EP0310556B1 - Verfahren zum endengleichen Färben von Cellulosefasern - Google Patents

Verfahren zum endengleichen Färben von Cellulosefasern Download PDF

Info

Publication number
EP0310556B1
EP0310556B1 EP88810652A EP88810652A EP0310556B1 EP 0310556 B1 EP0310556 B1 EP 0310556B1 EP 88810652 A EP88810652 A EP 88810652A EP 88810652 A EP88810652 A EP 88810652A EP 0310556 B1 EP0310556 B1 EP 0310556B1
Authority
EP
European Patent Office
Prior art keywords
formula
process according
independently
dyes
unsubstituted
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
EP88810652A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0310556A1 (de
Inventor
Jean-Marie Sire
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 AT88810652T priority Critical patent/ATE68836T1/de
Publication of EP0310556A1 publication Critical patent/EP0310556A1/de
Application granted granted Critical
Publication of EP0310556B1 publication Critical patent/EP0310556B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/68Preparing azo dyes on the material
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/22General 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/30General 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/62General 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 with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/628Compounds containing nitrogen
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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
    • D06P1/642Compounds containing nitrogen
    • D06P1/6429Compounds containing nitrogen bound to a six-membered aromatic carbocyclic ring
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916Natural fiber dyeing
    • Y10S8/918Cellulose textile

Definitions

  • the present invention relates to a novel process for dyeing textile cellulosic fibers with vat dyes, sulfur dyes, leuco vat ester dyes or azo development dyes using the padding process.
  • the foulard process is a dyeing process known for cellulose fibers, which allows large amounts of textile fiber materials to be dyed and soaked by impregnating or impregnating the fiber with the dye solution in a trough with the shortest liquor ratio and usually only once passing through the foulard with a short dyeing time then fix it.
  • Tailing / reverse tailing is the difference in strength and nuance between the beginning and end of a game. When only one dye is used, the end unevenness is noticeable in differences in strength, while shades in the shade can often also occur with combination dyeings.
  • Tailing is a weakening of the color strength between the beginning and end of the batch, which is due to a decrease in the dye concentration in the trough. This depletion of the dye in the liquor is caused by drawing up the dye in the padding process caused. Differences in strength and shade based on tailing occur particularly in the case of dyes with medium to high substantivity and very particularly often when coloring light shades.
  • Reverse tailing is an increase in color strength between the beginning and end of the batch, which is due to the increase in the dye concentration in the trough. This dye accumulation in the padding liquor is caused by a preferred water adsorption in the padding process. Differences in strength and shade based on reverse tailing occur with dyes of low substantivity, especially when coloring dark shades.
  • the azine compounds of formula (1) are preferred.
  • the colorless nitrogen-containing compound of formula (1) or (2) used in the process according to the invention is water-soluble and has substantivity for cellulose fibers, i.e. it is fiber-affine.
  • the amount of the fiber-affine compound in the processes according to the invention depends in particular on the amount of dye used, a minimum amount of 0.5 g / l and generally from 0.5 to 20 g / l, preferably 3 g / l to 10 g / l has proven to be very beneficial.
  • the fiber-affine compound contains 1 to 6, expediently 1 to 4, acidic water-solubilizing groups, which are in particular carboxyl groups or especially sulfonic acid groups.
  • the fiber-affine compound can contain only carboxyl groups or only sulfo groups as well as both carboxyl and sulfo groups.
  • the fiber-affine compound preferably contains 2 to 4 sulfonic acid groups.
  • C1-C5-alkyl means alkyl radicals or alkyl constituents which contain 1 to 5 carbon atoms and can be straight-chain or branched. Examples are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-amyl or isoamyl.
  • C1-C5 alkoxy examples are methoxy, ethoxy, isopropoxy, sec-butoxy, tert. Butoxy or tert-amyloxy.
  • aromatic or heteroaromatic radicals R1, R2 and R3 mean, for example, the phenyl, biphenylyl, naphthyl, stilbenyl, furfuryl or quinolinyl radical. Phenyl and naphthyl are preferred. In addition to Z, preferred substituents of these radicals are halogens and hydroxyl.
  • Halogen means for example fluorine, bromine or preferably chlorine.
  • the phen group hydroxy, cyano, nitro, halogen, C1-C5-alkyl, trifluoromethyl, C1-C5-alkoxy, C2-C5-alkoxycarbonyl, amino, mono- or di-C1-C5-alkylamino, phenylamino, carbamoyl, Sulfamoyl, ureido, C1-C7 acylamino, such as Acetylamino, propionylamino or benzoylamino, C1-C5 alkylsulfonyl, e.g. Contain methylsulfonyl, or sulfomethyl or sulfatoethyl.
  • the colorless nitrogen-containing compounds used in the process according to the invention are known per se or can be prepared by processes known per se. They are either in the form of the free acid or, preferably, as their salts.
  • suitable salts are the alkali, alkaline earth or ammonium salts or the salts of an organic amine. Examples include the sodium, potassium or ammonium salts or the salt of triethylamine or triethanolamine.
  • V is preferably R2-X2 ⁇ and W is especially R3-X3 ⁇ .
  • Azine compounds of the formula (1) in which X1, X2 and X3 each represent ⁇ NH- are particularly preferred.
  • aryl radical such as e.g. is a naphthyl or especially a phenyl radical.
  • V R2-X2 ⁇ and W are hydroxyl.
  • triazine compounds of the formula (5) in which X1, X2 and X3 each have ⁇ NH ⁇ , R1, R2 and R3, independently of one another, each phenyl or naphthyl, Z is the sulfonic acid group and m 2 to 4, preferably 2 or 3 mean.
  • triazine compounds of formula (6) in which V 'R2-X2 ⁇ and W' are hydroxyl.
  • colorless nitrogen-containing compounds which can be used according to the invention are and
  • Suitable cellulose fibers are natural fibers, such as mercerized or bleached cotton and linen (bleached), and regenerated fibers, such as viscose, rayon, polynosic and copper rayon. Mainly woven or knitted fabrics made of these fibers, especially cotton.
  • Fiber blends e.g. those made of polyester / cotton, the polyester portion being colored with disperse dyes, can also be used.
  • Suitable dyestuffs which can be used in the process according to the invention are the dyestuffs of the type mentioned which are customarily used for dyeing or printing cellulose textile materials.
  • the leuco vat ester dyes are e.g. from vat dyes of the indigo, anthraquinone or indanthrene series by reduction e.g. with iron powder and subsequent esterification e.g. available with chlorosulfonic acid and are referred to in the Color Index 3rd Edition, 1971, Vol. 3 as "Solubilized Vat Dyes".
  • vat dyes are, for example, higher fused and heterocyclic benzoquinones or naphthoquinones, in particular anthraquinone or indigoid dyes, especially sulfur dyes.
  • vat dyes which can be used according to the invention are listed in the Color Index 3rd Edition (1971) Vol. 3 on pages 3649 to 3837 under the names "Sulfur Dyes” and "Vat Dyes”.
  • the components for the azo development dyes are the color index 3rd edition 1971 as Azoic Coupling Components ("Naphthole”) and the chemical compounds listed as Azoic Diazo Components.
  • the amount of dyes in the process according to the invention generally depends on the desired color strength, with end unevenness especially in the case of light shades, i.e. at a concentration of 0.03 g / l to 10 g / l, preferably 0.05 to 6 g / l.
  • a particularly preferred embodiment of the process according to the invention consists in that an aqueous dye liquor is used which contains 1 to 6 g / l of dye and 3 to 10 g / l of azine compound.
  • the term g / l means grams per liter. For dyes, it refers to 100% powder trading form.
  • the dyeing liquors can contain other conventional additives in addition to the colorless compound, e.g. Alkali such as sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, trisodium phosphate, borax, aqueous ammonia, or alkali dispensers such as e.g. Sodium formate or sodium trichloroacetate, electrolytes such as e.g. Contain sodium chloride or sodium sulfate as well as urea, thiourea or glycerin. If necessary, thickeners such as e.g. Alginates, starch ether or locust bean gum may be contained therein.
  • Alkali such as sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, trisodium phosphate, borax, aqueous ammonia
  • alkali dispensers such as e.g. Sodium formate or sodium trichloroacetate, electrolytes such as e.g. Contain
  • Sodium dithionite sodium hydrosulfite
  • the linking is usually carried out in an alkaline medium.
  • alkali-resistant wetting agents e.g. Sulfonates of polycarboxylic acid esters, e.g. Dihexyl sulfosuccinate or dioctyl sulfosuccinate; Straight chain or branched chain alkylarylsulfonates with at least 6 carbon atoms, e.g. Dodecylbenzenesulfonates or preferably alkylsulfonates whose alkyl chain contains 8 to 20 carbon atoms, e.g. Add dodecyl sulfonates or pentadecyl sulfonates.
  • the sulfonates mentioned as wetting agents are generally present as alkali metal salts, in particular as sodium salts or also as ammonium salts.
  • the amounts in which the wetting agents are added to the dyeing liquor are more appropriately between 0.2 to 10 g, preferably 0.5 to 3 g, per liter of liquor.
  • the dye fixation on pure cellulose fibers is carried out by customary methods, the fixing time and fixing temperature depending on the fiber material and on the dye. Steaming times in saturated steam between 30 seconds and 5 minutes at 100 to 105 ° C. are generally sufficient to achieve a uniform and optimal dye fixation. High-temperature steaming or dry heat steaming is used to fix at 105-190 ° C for 20 seconds to 3 minutes. In particular, the dyes are fixed with steam at a temperature of 100 ° C to 120 ° C for 30 seconds to 3 minutes. If necessary, the textile material is dried before fixing.
  • fixation can also be carried out by the cold dwell process, such as 6 to 24 hours residence time at room temperature.
  • the dyed cellulose material can be washed out in a conventional manner in order to remove unfixed dye.
  • the substrate is treated, for example, at from 40 ° C. to cooking temperature in a solution which contains soap or synthetic detergent. Treatment with a fixative can then be carried out to improve wet fastness.
  • the dyeings are completed by rinsing in hot and / or cold water and, if appropriate, with subsequent washing in the presence of a commercially available detergent, followed by rinsing in water and drying.
  • the dive time is 3 seconds.
  • the fabric is steamed at 101-103 ° C for one minute and rinsed with water at 25 ° C.
  • the dyeing is then oxidized with 5 ml of hydrogen peroxide for 2 minutes at 70 ° C., then soaped and rinsed hot and cold.
  • a cotton cord fabric dyed in the same shade of red with very good fastness properties is obtained.
  • Example 1 If one proceeds as described in Example 1, but uses a liquor without the triazine compound of the formula (8), a cotton cord fabric dyed in a different shade of red is obtained, the beginning of the lot being darker in color compared to the end of the lot, because the squeezed liquor is depleted of dye and thus diluted.
  • the dyeing is treated with saturated steam at 101 ° C for 90 seconds and rinsed cold, then the dyeing is oxidized at 70 ° C for 60 seconds with 7 ml / l hydrogen peroxide, boiling soaped with 1 g / l detergent, hot and rinsed cold and dried.
  • the fabric is rinsed cold, neutralized with an aqueous solution containing 2 g / l sodium carbonate, soaped at the boil, rinsed hot and cold and finally dried.
  • a cotton fabric dyed in the same shade of blue with very good fastness properties is obtained.
  • the cotton cretonne fabric After 30 seconds of air, the cotton cretonne fabric is dried in a hot flue at 120 ° C. for 45 seconds. The color is then developed by impregnation on the pad with a squeezing effect of 80% liquor absorption with an aqueous liquor which contains 13 g / l of an Azoic Diazo Component 1 with a CI No. 37135. The dive time is 6 seconds. After passing the development pad, there is an air passage of 30 seconds. The cotton cretonne fabric is then rinsed with water at 70 ° C., soaped at the boil with 2 g / l detergent, rinsed hot and cold and dried.
  • the fabric is rinsed cold, neutralized with an aqueous solution containing 2 g / l sodium carbonate, soaped at the boil, rinsed hot and cold and finally dried.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP88810652A 1987-10-01 1988-09-23 Verfahren zum endengleichen Färben von Cellulosefasern Expired - Lifetime EP0310556B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT88810652T ATE68836T1 (de) 1987-10-01 1988-09-23 Verfahren zum endengleichen faerben von cellulosefasern.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH382387 1987-10-01
CH3823/87 1987-10-01

Publications (2)

Publication Number Publication Date
EP0310556A1 EP0310556A1 (de) 1989-04-05
EP0310556B1 true EP0310556B1 (de) 1991-10-23

Family

ID=4264234

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88810652A Expired - Lifetime EP0310556B1 (de) 1987-10-01 1988-09-23 Verfahren zum endengleichen Färben von Cellulosefasern

Country Status (8)

Country Link
US (1) US4886518A (xx)
EP (1) EP0310556B1 (xx)
JP (1) JPH01111078A (xx)
KR (1) KR890006914A (xx)
AT (1) ATE68836T1 (xx)
DE (1) DE3865800D1 (xx)
ES (1) ES2027036T3 (xx)
ZA (1) ZA887308B (xx)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0584044B1 (de) * 1992-08-18 1997-07-16 Ciba SC Holding AG Verfahren zur photochemischen und thermischen Stabilisierung von ungefärbten und gefärbten Polyesterfasermaterialien
DE59709127D1 (de) 1996-07-08 2003-02-20 Ciba Sc Holding Ag Triazinderivate als UV-Filter in Sonnenschutzmitteln
BRPI0804658B1 (pt) * 2008-08-11 2012-06-26 processo de tingimento têxtil de fibras celulósicas e suas combinações com outras fibras com banhos de tingimentos reutilizados, sem realizar nenhum tratamento de depuração posterior.
CN117005215B (zh) * 2023-08-16 2024-02-23 韶关市北纺智造科技有限公司 一种硫化黑染液及其应用

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2298533A (en) * 1942-10-13 Capillary active condensation
US2928711A (en) * 1960-03-15 New colouration process
CH155747A (de) * 1931-02-10 1932-07-15 Chem Ind Basel Küpenfarbstoffpräparat.
US2940814A (en) * 1953-12-04 1960-06-14 Gen Aniline & Film Corp Vat dye compositions containing pyrimidines
US3400121A (en) * 1966-03-30 1968-09-03 Hoechst Ag 2, 4, 6-tri-(1-amino-substituted aromatic)-s-triazines
CH610702B (de) * 1976-06-16 Ciba Geigy Ag Verfahren zur verbesserung von mit anionischen farbstoffen auf cellulosetextilmaterial erzeugten faerbungen.
DE2930756A1 (de) * 1979-07-28 1981-02-26 Cassella Ag Klotzhilfsmittel und verfahren zum faerben von cellulosefasern bzw. gemischen von cellulosefasern zusammen mit synthesefasern mit schwefel-, schwefelkuepen-, kuepen- und reaktivfarbstoffen
US4313732A (en) * 1980-10-30 1982-02-02 Burlington Industries, Inc. Process for improving washfastness of indigo-dyed fabrics
DE3174788D1 (en) * 1980-12-30 1986-07-10 Ciba Geigy Ag Process for dyeing or printing cellulosic materials and mixed cellulose/polyester fabrics
DE3247727A1 (de) * 1982-12-23 1984-06-28 Hoechst Ag, 6230 Frankfurt Nuancierverfahren unter verwendung reaktiver und nicht reaktiver farbstoffe
ATE47168T1 (de) * 1986-04-07 1989-10-15 Ciba Geigy Ag Verfahren zum endengleichen faerben von cellulosefasern.

Also Published As

Publication number Publication date
ZA887308B (en) 1989-06-28
US4886518A (en) 1989-12-12
DE3865800D1 (de) 1991-11-28
ES2027036T3 (es) 1992-05-16
ATE68836T1 (de) 1991-11-15
EP0310556A1 (de) 1989-04-05
KR890006914A (ko) 1989-06-16
JPH01111078A (ja) 1989-04-27

Similar Documents

Publication Publication Date Title
EP0040790B2 (de) Verfahren zum Färben und Bedrucken von Hydroxy- und/oder Carbonamidgruppen enthaltenden Fasermaterialien
DE1265698B (de) Verfahren zur Erzeugung von nassechten Faerbungen und Drucken
DE1619636A1 (de) Verfahren zum Faerben und Bedrucken
EP0310556B1 (de) Verfahren zum endengleichen Färben von Cellulosefasern
DE1059399B (de) Verfahren zum Faerben und Bedrucken von cellulosehaltigen Textilien
DE2238552A1 (de) Verfahren zum faerben von cellulosetextilien
EP0242324B1 (de) Verfahren zum endengleichen Färben von Cellulosefasern
EP0352222B1 (de) Faserreaktive Formazanfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung
CH485360A (fr) Moteur électrique synchrone monophasé de petites dimensions
DE1235257B (de) Verfahren zum Faerben oder Bedrucken von cellulosehaltigen Materialien faseriger Struktur
US3249394A (en) Vat dyeing with thiosulfate dyes
DE2757681C2 (de) Phenylazopyridon-Verbindung, Verfahren zu deren Herstellung, ihre Verwendung zum Färben oder Bedrucken von Fasermaterial aus natürlicher oder regenerierter Cellulose oder aus natürlichen, regenerierten oder synthetischen Polyamiden
EP0857762B1 (de) Wässrige Reaktivfarbstoff-Formulierungen sowie Verfahren zum Färben und Bedrucken von textilen Fasermaterialien
EP3521379A1 (de) Faserreaktive azofarbstoffe sowie farbstoffgemische, verfahren zu ihrer herstellung und ihre verwendung zum färben oder bedrucken
EP0410931A2 (de) Faserreaktive Formazanfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung
AT203457B (de) Verfahren zum Färben polyhydroxylierter Materialien nach dem Direktfärbeverfahren aus langer Flotte
EP0410930A2 (de) Faserreaktive Formazanfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung
DE1619543C3 (de) Verfahren zur Herstellung echter Färbungen oder Drucke auf Cellulosefasermaterialien mit wasserlöslichen Reaktivfarbstoffen
CH639121A5 (en) Monoazo compounds having a fibre-reactive radical, preparation thereof and use thereof in dyeing and printing leather
DE1229493B (de) Verfahren zum Faerben oder Bedrucken von Cellulose-Textilmaterialien
DE2638221C2 (de) Verfahren zum einbadigen Färben von Mischgeweben aus Cellulose- und Polyamidfasern
DE1923539C3 (de) Phthalocyaninfarbstoffe, deren Herstellung und Verwendung
AT219000B (de) Verfahren zur Herstellung von naßechten Färbungen und Drucken auf Cellulosematerialien
CH423708A (de) Verfahren zum Färben und Bedrucken von Textilmaterialien
DE1262213B (de) Verfahren zum Faerben oder Bedrucken von cellulosehaltigen Materialien faseriger Struktur

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19880926

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE ES FR LI

17Q First examination report despatched

Effective date: 19910208

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE ES FR LI

REF Corresponds to:

Ref document number: 68836

Country of ref document: AT

Date of ref document: 19911115

Kind code of ref document: T

ET Fr: translation filed
REF Corresponds to:

Ref document number: 3865800

Country of ref document: DE

Date of ref document: 19911128

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2027036

Country of ref document: ES

Kind code of ref document: T3

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 19940816

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 19940912

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19941215

Year of fee payment: 7

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: AT

Effective date: 19950923

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF THE APPLICANT RENOUNCES

Effective date: 19950925

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Effective date: 19950930

Ref country code: CH

Effective date: 19950930

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

BECN Be: change of holder's name

Effective date: 19961129

REG Reference to a national code

Ref country code: FR

Ref legal event code: TP

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19970421

Year of fee payment: 10

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19970430

Year of fee payment: 10

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19971104

Year of fee payment: 10

REG Reference to a national code

Ref country code: FR

Ref legal event code: CD

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19980930

BERE Be: lapsed

Owner name: CIBA SPECIALTY CHEMICALS HOLDING INC.

Effective date: 19980930

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19990531

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19990701

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 19991102