EP0357548B1 - Verfahren zum Färben und Bedrucken von cellulosischen Fasermaterialien mit Küpenfarbstoffen - Google Patents

Verfahren zum Färben und Bedrucken von cellulosischen Fasermaterialien mit Küpenfarbstoffen Download PDF

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Publication number
EP0357548B1
EP0357548B1 EP89810553A EP89810553A EP0357548B1 EP 0357548 B1 EP0357548 B1 EP 0357548B1 EP 89810553 A EP89810553 A EP 89810553A EP 89810553 A EP89810553 A EP 89810553A EP 0357548 B1 EP0357548 B1 EP 0357548B1
Authority
EP
European Patent Office
Prior art keywords
dyeing
weight
vat
process according
vat dyes
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 - Lifetime
Application number
EP89810553A
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German (de)
English (en)
French (fr)
Other versions
EP0357548A1 (de
Inventor
Walter Marte
Paul Prof. Dr. Rys
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Priority to AT89810553T priority Critical patent/ATE66260T1/de
Publication of EP0357548A1 publication Critical patent/EP0357548A1/de
Application granted granted Critical
Publication of EP0357548B1 publication Critical patent/EP0357548B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/22—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
    • D06P1/22—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
    • 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
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile

Definitions

  • the present invention relates to a process for dyeing and printing cellulosic fiber materials with vat dyes in the presence of endiols as reducing agents and alkali.
  • the dyeing and printing of cellulosic fiber materials with vat dyes is generally carried out in alkaline media with sodium dithionite (hydrosulfite) as a reducing agent and usually in the presence of considerable amounts of complexing agents.
  • Hydrosulfite already has a high reducing power at low temperature, but is sensitive to oxygen in alkaline solution. Oxidation of the hydrosulfite creates sodium sulfate, which can only be incompletely removed from the paint waste water.
  • Wastewater with a high sulfite / sulfate load is corrosive and can e.g. Destroy sewage pipes (concrete pipes). If sulfate deposits occur, anaerobic degradation can also result in hydrogen sulfide.
  • the presence of the complexing agents in the waste water is also problematic.
  • FR-A-2164824 a process for dyeing and printing cellulosic fiber materials with vat or sulfur dyes is known, in which, as the reducing agent, reductones, etc. also endiols, which are characterized by strongly negative redox potentials in alkaline medium, and quinoid compounds are used as oxidation stabilizers.
  • BE-A-686620 discloses a similar process which is carried out in the presence of an aldehyde sulfoxylate, in particular formaldehyde sulfoxylate, and a colorless, saturated carbonyl compound as an oxidation stabilizer.
  • the present invention therefore relates to a process for dyeing and printing cellulosic fiber materials with vat dyes in the presence of endiols as reducing agents and alkali, characterized in that organic, water-miscible solvents from the group of low molecular weight alcohols, ketones, are additionally used to reduce the vat dyes , Ethers, acetals, glycols, glycol ethers, thioglycols, nitriles, pyridines, lactones, lactams, acid amides, ureas, sulfones, sulfoxides or alkanolamines.
  • the process according to the invention for dyeing cellulosic fiber materials with vat dyes from aqueous alkaline dye liquors and in the presence of endiols as reducing agents is characterized in that the dye liquors additionally contain 0.1 to 10% by weight of the water-miscible organic solvent.
  • the invention furthermore relates to the aqueous alkaline dye liquors or printing pastes for carrying out the dyeing process according to the invention, vat dye preparations (stock vats) from which the dye liquors / printing pastes can be produced, and the dyed and printed (textile) cellulosic fiber materials obtained according to the process.
  • Vat dyes in the sense of the present invention are to be understood in addition to the indigoid dyes, with indigo itself being preferred also to mean anthrachinoid dyes and possibly also non-pre-reduced sulfur dyes. See the sections for details Vat and sulfur dyes (vat / sulfur dyes) in the Color Index (CI), third edition, 1971, published by the Society of Dyers and Colors.
  • aqueous alkaline liquors in which the dyeings are carried out are strongly alkaline, i.e. they have pH values in the range from about 11 to 14, preferably 12 to 14 or 13 to 14.
  • the pH values are generally set using aqueous alkali metal hydroxide, in particular sodium hydroxide, and optionally also potassium hydroxide solutions.
  • Endiols are used to reduce vat dyes in the process according to the invention.
  • these are ⁇ -hydroxycarbonyl compounds which are distinguished by a strongly reducing action in an alkaline medium.
  • Typical compounds that form endiols (endiolates) in an alkaline medium are, in particular, low molecular weight (C2-C6) ⁇ -hydroxyketones and ⁇ -hydroxyaldehydes, such as e.g. Monohydroxyacetone, dihydroxyacetone, glycol aldehyde, dihydroxybutanone, 2,3-dihydroxyacrylaldehyde (triose reductone), ascorbic acid, cyclopentenediol-one (reductic acid).
  • C2-C6 low molecular weight
  • ⁇ -hydroxyketones and ⁇ -hydroxyaldehydes such as e.g. Monohydroxyacetone, dihydroxyacetone, glycol aldehyde, dihydroxybutanone, 2,3-dihydroxyacrylaldehyde (triose reductone), ascorbic acid, cyclopentenediol-one (reductic acid).
  • Mono- and dihydroxyacetone are particularly preferred.
  • the reducing agents are generally used in amounts of about 20 to 100% by weight, preferably 20 to 80% by weight, based on the dye.
  • organic solvents which are suitable for the process according to the invention should be miscible with water, ie with at least in the stated amounts from 0.1 to 10, in particular from 0.1 to 5% by weight in which they are used in the dye baths Water form a homogeneous phase.
  • the solvents mentioned should preferably still be miscible with water in a much larger amount, ie somewhat to 50% by weight (range 0, 1 to 50% by weight).
  • the process according to the invention which is carried out using a combination of endiols as reducing agents and organic, water-miscible solvents, is practically suitable for all dyeing and printing processes with vat dyes, in particular indigo.
  • the method according to the invention is also suitable for continuous dyeing, e.g. Suitable as a pad-steam process or as a cold storage process.
  • the vat dye as a pigment
  • the textile material which is then usually dried; then an aqueous liquor with the reducing agent / solvent combination is applied and at higher temperatures, e.g. in a steam atmosphere at 100 ° C, developed (reduced) and then, as usual, e.g. Rinsing, oxidizing and soaping finished.
  • the pad-steam process using hydroxyacetone as the reducing agent results in a saving of more than 50% by weight of reducing agent compared to the dithionite previously used for this process.
  • the process according to the invention can also be carried out as a single-bath padding process by applying an aqueous liquor, which contains the vat dye, alkali, the reducing agent and the organic solvent, to the textile material and developing the dyeing by steaming or cold storage and then finishing as usual.
  • an aqueous liquor which contains the vat dye, alkali, the reducing agent and the organic solvent
  • the method according to the invention can also be carried out as a printing method, e.g. as a two-phase printing process by printing on the vat dyes with a printing paste containing conventional thickeners and reducing agents, intermediate drying, padding on a padding liquor containing solvents and alkali, and developing in a damper suitable for two-phase printing, again being finished as usual by rinsing, oxidizing and soaping.
  • a printing method e.g. as a two-phase printing process by printing on the vat dyes with a printing paste containing conventional thickeners and reducing agents, intermediate drying, padding on a padding liquor containing solvents and alkali, and developing in a damper suitable for two-phase printing, again being finished as usual by rinsing, oxidizing and soaping.
  • the printing paste contains the dye, thickener, alkali, reducing agent and solvent.
  • aqueous dyeing liquors / printing pastes for carrying out the dyeing process according to the invention from a bath are a further subject of the present invention. They are characterized in that they contain the vat dye, an alkali metal hydroxide, an endiol as a reducing agent and 0.1 to 10% by weight, based on the dyeing liquor / printing paste, a water-miscible organic solvent and other conventional auxiliaries.
  • the amounts of dye, alkali and reducing agent in these dyeing liquors can vary within wide limits.
  • the amount of dye which is dependent on the desired depth of color, is 0.1 to 7% by weight, based on the substrate to be colored.
  • the amount of alkali should be sufficient to set a pH in the range from 11 to 14, preferably 12 to 14 or 13 to 14.
  • the amount of reducing agent is about 0.01 to 10 wt .-%, based on the weight of the dye liquor.
  • vat dye preparations - and these are a further subject of the present invention - can be used, in addition to the vat dye, the reducing agents and solvents mentioned, and optionally also conventional auxiliaries such as dispersing and adjusting agents, and water.
  • the amount of reducing agent is about 1 to 2, preferably 1.4 to 1.6, so-called linking equivalents per equivalent of dye, the linking equivalent being the amount of reducing agent which can ensure adequate (complete) linking.
  • the amount of solvent is chosen so that the specified amount of 0.1 to 10% by weight is present after the dyeing liquors have been prepared.
  • the amount of water depends on whether it is solid, dough-like or liquid vat dye preparations.
  • vat dyes can be linked during the actual dyeing / printing process, but also separately (pre-linked dye preparations which can be used to produce dyeing liquors or printing pastes).
  • the (pre) linking of the dyes and the actual dyeing and printing of textile materials can also be continuously connected to one another by directly using the (stable) preparations with the linked dyes for dyeing and printing
  • vat dye preparations or the dyebaths / printing pastes can, if appropriate, also be improved further by adding water, alcohols, reducing agents, surfactants, alkali metal hydroxides and other components from the suspensions containing the sparingly soluble vat dyes optionally contain other conventional additives, uses ultrasound.
  • Dye preparations or dyebaths or printing pastes can be obtained by such an ultrasonication, which have a much more homogeneous and fine-grained distribution of vat dyes, which at the same time enables an improved reduction (higher concentration of the conjugated dye) and thus also a higher dye yield on the substrate.
  • the amount of reducing agents and the other components used can thus generally be reduced.
  • the procedure is generally such that the dye suspension is first stirred and then the dye agglomerates are ground using ultrasound.
  • the process of dissolving and combining the vat dyes can thus be shortened considerably; as indicated, this also opens up the possibility of continuously carrying out the dyeing process with the vat dyes.
  • the ultrasonic waves that are used according to the method are generated in a conventional ultrasonic generator.
  • Their frequency is in the range of 16 kHz and above, e.g. in the range from 18 to 35 kHz, preferably 20 to 25 kHz.
  • the ultrasonic energy to be used depends on the type of dye but also on the other reaction conditions, such as temperature, solvent, grain size of the dye, etc. Typically, 50 to 100 watts (5 to 10 mkg / s) of energy is sufficient for dye preparations as used in the examples below.
  • the process according to the invention for dyeing and printing with vat dyes can be used for cellulosic fiber materials in a wide variety of textile processing states.
  • the appropriate dyes e.g. acid or dispersion dyes
  • the process according to the invention achieves surprising advantages in the field of dyeing and printing cellulosic textile fiber materials with vat dyes, in particular indigo.
  • vat dyes no over-reduction
  • the high stability of the reduced (combined) dye liquor no precipitation of the combined dye up to relatively high concentrations - which is particularly important when using so-called vats, which should have a sufficiently long service life (several hours). This makes dyeing in deep shades easier and gives you level dyeings.
  • the dyestuffs can optionally be recovered from the dyeing wastewater in a relatively simple manner and without being disturbed by excessive salt content, e.g. through ultrafiltration.
  • organic components can be removed from the wastewater and this wastewater purified in this way can finally be returned to the dyeing process.
  • the solvents can at least partially be recovered and reused or otherwise used.
  • Pre-cleaned cotton fabric is placed in a jigger containing a dye liquor of the following composition:
  • the temperature of the fleet is 50 ° C.
  • the liquor ratio is 1: 6.
  • the fabric After a dyeing time of 30 minutes, the fabric is oxidized and soaped as usual.
  • the residual dye is recovered from the almost exhausted fleet by means of ultrafiltration and the residual waste water can be sent directly to biological disposal and reused if necessary.
  • Raw yarn is dyed continuously at a speed of 40 m / minute in a corresponding dyeing machine using a stock vat method.
  • the stock vat is continuously introduced into the dye bath at a 1:20 dilution.
  • the trunk is linked outside the dye bath at 50 ° C.
  • the trunk has the following composition:
  • the temperature of the dye liquor is 40 ° C.
  • the liquor absorption is 60% by weight.
  • the dye pigment detached during the washing process is recovered using an ultrafiltration system and the permeate is disposed of anaerobically.
  • a cotton fabric is printed with a printing paste containing a non-pre-reduced sulfur dye and monohydroxyacetone and dried. This is followed by padding on an aqueous solution containing alkali and solvent of the following composition:
  • a black-dyed cotton fabric with good levelness is obtained.
  • the process is characterized by its good reproducibility in terms of color strength and levelness. Another advantage is the high durability of the paste despite the presence of the reducing agent.
  • Pre-cleaned cotton fabric is dyed in a jigger containing the following dye liquors:
  • the liquor ratio is 1:20, the pH 13.1. After a dyeing time of 45 minutes, the fabric is oxidized and soaped as usual.
  • ethanol instead of methanol, you can also use ethanol, n-propanol, iso-propanol, n-butanol, acetone, methyl ethyl ketone, cyclohexanone, diisopropyl ether, dioxane, tetrahydrofuran, glycerol formal, glycol formal, ethylene glycol, propylene glycol, ethylene glycol dimethyl ether, ethylene glycol monomethyl ether, with analog results - or -butyl ether, diethylene glycol monomethyl or ethyl ether, thiodiglycol, acetonitrile, pyridine, ⁇ -butyrolactone, pyrrolidone, N-methylpyrrolidone, 1,5-dimethylpyrrolidone, formamide, N, N-dimethylformamide, acetamide, N, N-dimethylacetamide, tris - (Dimethylamido) phosphate,
  • Cotton fabric is placed on a commercial jet system at a fleet. ratio of 1:10 at 55 to 60 ° C.
  • the dyebath is prepared in a similar way to a vat process:
  • the trunk has the following composition:
  • the viling takes place at 55 ° C; the pH is 12.9. After about 20 minutes of reaction, the stock vat is diluted 1: 5 with water.
  • the dye liquor obtained in this way is pumped into the dyeing machine and circulated there at 55 to 60 ° C. for 45 minutes. It is then oxidized and finished as usual.
  • the veneer can also be sonicated by the trunk (55 ° C, frequency: 20 kHz, 50 to 100 watts), e.g. for dyes C.I. Vat Red 10 or C.I. Vat Green 3, speed up.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
EP89810553A 1988-07-29 1989-07-20 Verfahren zum Färben und Bedrucken von cellulosischen Fasermaterialien mit Küpenfarbstoffen Expired - Lifetime EP0357548B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT89810553T ATE66260T1 (de) 1988-07-29 1989-07-20 Verfahren zum faerben und bedrucken von cellulosischen fasermaterialien mit kuepenfarbstoffen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH2891/88A CH680180B5 (enrdf_load_stackoverflow) 1988-07-29 1988-07-29
CH2891/88 1988-07-29

Publications (2)

Publication Number Publication Date
EP0357548A1 EP0357548A1 (de) 1990-03-07
EP0357548B1 true EP0357548B1 (de) 1991-08-14

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP89810553A Expired - Lifetime EP0357548B1 (de) 1988-07-29 1989-07-20 Verfahren zum Färben und Bedrucken von cellulosischen Fasermaterialien mit Küpenfarbstoffen

Country Status (13)

Country Link
US (1) US4950306A (enrdf_load_stackoverflow)
EP (1) EP0357548B1 (enrdf_load_stackoverflow)
JP (1) JPH02133684A (enrdf_load_stackoverflow)
KR (1) KR900001924A (enrdf_load_stackoverflow)
CN (1) CN1036148C (enrdf_load_stackoverflow)
AT (1) ATE66260T1 (enrdf_load_stackoverflow)
BR (1) BR8903787A (enrdf_load_stackoverflow)
CH (1) CH680180B5 (enrdf_load_stackoverflow)
DE (1) DE58900214D1 (enrdf_load_stackoverflow)
ES (1) ES2025380B3 (enrdf_load_stackoverflow)
IE (1) IE61204B1 (enrdf_load_stackoverflow)
YU (1) YU151689A (enrdf_load_stackoverflow)
ZA (1) ZA895767B (enrdf_load_stackoverflow)

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EP3927879B1 (de) * 2019-02-19 2023-05-10 Gebrüder Otto Baumwollfeinzwirnerei GmbH & Co. KG Verfahren zur herstellung farbiger fasermaterialien und deren verwendung

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US5611818A (en) * 1991-05-23 1997-03-18 Sandoz Ltd. Dry leuco sulphur dyes in particulate form
DE4230870A1 (de) * 1992-09-16 1994-03-17 Basf Ag Verfahren zum Färben und Bedrucken von textilen Materialien aus Cellulosefasern
US5961670A (en) * 1995-05-03 1999-10-05 Clariant Finance (Bvi) Limited Sulfur dyes
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ITMI20020204A1 (it) * 2002-02-05 2003-08-05 Pinuccio Giordano Procedimento per la tintura di materiale tessile
JP2004332148A (ja) * 2003-05-07 2004-11-25 Tango Orimono Kogyo Kumiai ポリエステル系繊維製品の藍染め方法
DE102004014764A1 (de) * 2004-03-26 2005-10-06 Wella Ag Haarfärbemittel mit Küpenfarbstoffen
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JP4771057B2 (ja) * 2005-02-15 2011-09-14 カール事務器株式会社 パンチ補助具及び補助具付きパンチ
CN1308542C (zh) * 2005-04-15 2007-04-04 夏建明 活性染料染色用液体固色碱剂
US8523957B2 (en) * 2005-08-09 2013-09-03 Sanko Tekstil Isletmeleri San. Ve Tic. A.S. Process for introducing vat dyes and chemicals into textiles
US20070107136A1 (en) * 2005-08-17 2007-05-17 Tao Xiao-Ming Method and apparatus for wet treatment of textiles and textile articles at low temperatures
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FR2949334B1 (fr) * 2009-09-02 2015-10-23 Oreal Composition comprenant un colorant hydrophobe, un compose organique particulier i et un compose particulier ii, et utilisation en coloration
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CN107558253B (zh) * 2017-08-23 2020-01-10 四川省宜宾惠美线业有限责任公司 一种用还原染料染色人棉纤维的方法
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EP3927879B1 (de) * 2019-02-19 2023-05-10 Gebrüder Otto Baumwollfeinzwirnerei GmbH & Co. KG Verfahren zur herstellung farbiger fasermaterialien und deren verwendung

Also Published As

Publication number Publication date
CH680180B5 (enrdf_load_stackoverflow) 1993-01-15
YU151689A (en) 1991-04-30
EP0357548A1 (de) 1990-03-07
ES2025380B3 (es) 1992-03-16
BR8903787A (pt) 1990-03-20
ATE66260T1 (de) 1991-08-15
JPH0545718B2 (enrdf_load_stackoverflow) 1993-07-09
ZA895767B (en) 1990-03-28
CN1039860A (zh) 1990-02-21
US4950306A (en) 1990-08-21
CN1036148C (zh) 1997-10-15
IE892465L (en) 1990-01-29
KR900001924A (ko) 1990-02-27
JPH02133684A (ja) 1990-05-22
CH680180GA3 (enrdf_load_stackoverflow) 1992-07-15
DE58900214D1 (de) 1991-09-19
IE61204B1 (en) 1994-10-19

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