EP0419413A1 - Procédé de teinture ou d'impression de fibres mélangées contenant des fibres de cellulose et de la soie - Google Patents

Procédé de teinture ou d'impression de fibres mélangées contenant des fibres de cellulose et de la soie Download PDF

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Publication number
EP0419413A1
EP0419413A1 EP19900810694 EP90810694A EP0419413A1 EP 0419413 A1 EP0419413 A1 EP 0419413A1 EP 19900810694 EP19900810694 EP 19900810694 EP 90810694 A EP90810694 A EP 90810694A EP 0419413 A1 EP0419413 A1 EP 0419413A1
Authority
EP
European Patent Office
Prior art keywords
formula
amino
reactive dyes
silk
dye
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.)
Ceased
Application number
EP19900810694
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German (de)
English (en)
Inventor
Friedhelm Niemann
Hermann Flensberg
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
Ciba Geigy GmbH
Original Assignee
Ciba Geigy AG
Ciba Geigy GmbH
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, Ciba Geigy GmbH filed Critical Ciba Geigy AG
Publication of EP0419413A1 publication Critical patent/EP0419413A1/fr
Ceased 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
    • 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
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8219—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and amide 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
    • D06P1/38—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 reactive 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
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8214—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester and amide groups
    • 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
    • Y10S8/917—Wool or silk
    • 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 invention relates to a new process for dyeing or printing mixed fibers made of cellulose-containing fiber materials and silk with reactive dyes by impregnating these mixed fibers with reactive dyes and then steaming them.
  • Reactive dyes have long been used extensively for dyeing and printing textiles made of fiber materials. In view of the increasing demands on reactive dyeing in terms of economy, application technology and authenticity level, the technical level achieved is often not fully satisfactory. In recent years, efforts have also been made to optimize dyeing processes, both in terms of the choice of dyes and in terms of the dyeing process. In order to achieve satisfactory and reproducible results here, one has to rely on dyeing processes, e.g. characterized by the following criteria: simplest process control, good structure of the dyes on the fiber and complete fixation.
  • a particularly interesting problem relates to the dyeing of fiber mixtures, in particular of cellulose-containing fiber materials with silk, such as e.g. Viscose silk or cotton / silk fiber blends.
  • the problem of tone-on-tone dyeing of both fiber materials arises, which has hitherto led to the subjecting of fiber mixtures of cellulose-containing fiber materials and silk to two different dyeing processes, i.e. on the one hand, a dyeing process with dyes for one type of fiber with post-treatment and then a dyeing process with other dyes for the other type of fiber with post-treatment.
  • a dyeing process with dyes for one type of fiber with post-treatment i.e. on the one hand, a dyeing process with dyes for one type of fiber with post-treatment and then a dyeing process with other dyes for the other type of fiber with post-treatment.
  • Such a process consisting of two dyeing processes is cost-intensive and time-consuming.
  • the method according to the invention allows the dyeing or printing of mixed fibers from cellulose-containing fiber materials and silk with reactive dyes in order to achieve good tone-on-tone dyeing of both types of fiber in the simplest way, without having the disadvantages mentioned.
  • the method according to the invention is particularly suitable for dyeing the mixed fibers mentioned.
  • radical D in formula (1) can be substituted in the customary manner, in particular the radical D contains one or more sulfonic acid groups.
  • alkyl groups with 1 to 4 carbon atoms such as methyl, ethyl, propyl, isopropyl and butyl
  • alkoxy groups with 1 to 4 carbon atoms such as methoxy, ethoxy, propoxy, isopropoxy and butoxy
  • alkanoylamino groups with 1 up to 6 carbon atoms such as acetylamino and propionylamino
  • benzoylamino amino, alkylamino with 1 to 4 carbon atoms, phenylamino, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy radical, nitro, cyano, trifluoromethyl, halogen, such as fluorine, chlorine and bromine, sulfamoyl, carbamoyl.
  • Ureido hydroxy, carboxy, sulfomethyl and sulfo.
  • Those reactive dyes in which D is the residue of an azo dye contain, in particular, methyl, ethyl, methoxy, benzoylamino, amino, acetylamino, ureido, sulfomethyl, hydroxy, carboxy, halogen or sulfo as substituents.
  • the radical of an optionally substituted C 1 -C 4 -alkyl radical R is, for example, a straight-chain or branched radical which can be further substituted, for example by halogen, hydroxy, aminosulfonyl, cyano, alkoxy, alkoxycarbonyl, carboxy, sulfato or sulfo, or an unsubstituted alkyl radical with 1 to 4 carbon atoms.
  • R examples are: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, carboxymethyl, ⁇ -carboxyethyl, ⁇ -carboxypropyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, ⁇ -methoxyethyl, ⁇ -ethoxyethyl , ⁇ -methoxypropyl, ⁇ -chloroethyl, y-chloropropyl, y-bromopropyl, ß-hydroxyethyl, ⁇ -hydroxybutyl, ß-cyanoethyl, sulfomethyl, ß-sulfoethyl, aminosulfonylmethyl, ß-sulfatoethyl.
  • the residue Y is e.g. into consideration: a, ß-dichloroethyl, a, ß-dibromoethyl, a-chlorovinyl and a-bromovinyl.
  • the dyes of the formula (1) contain at least one fiber-reactive radical of the formula (3).
  • Fiber-reactive compounds are to be understood as those which are able to react with the hydroxyl groups of cellulose or with the amino groups of natural or synthetic polyamides to form covalent chemical bonds.
  • the reactive dyes of the formula (1) which can be used according to the invention are known. They can be made by using a dye of the formula or a dye precursor with at least one equivalent of an acyl halide of the formula wherein Hal is a halogen atom, acylated, where D, R and Y in the formulas (4) and (5) have the meanings given under formula (1), and that, if dye precursors are used, they are converted into the desired end dyes .
  • the process variant which starts from dye precursors, is suitable for the preparation of reactive dyes of the formula (1), in which D is the remainder of a dye composed of two or more than two components.
  • dyes composed of two or more than two components are: monoazo, disazo, trisazo, tetrazo, metal complexazo, formazan and azomethine dyes.
  • a diazo component which, in addition to the amino group to be diazotized, contains a group -N (R) H or a coupling component which contains a group -N (R) H can be reacted with an acyl halide of the formula (5), and then convert the product obtained into the desired azo dye by coupling with the other component and, if appropriate, connect a further conversion reaction.
  • reactive dyes of the formula (1) which contain two reactive dyes can be prepared by using a diazo component and a coupling component, each of which contains a group -N (R) H, and acylated before or after the coupling.
  • Dyes of the formula (1) which contain two reactive radicals can also be prepared by using dyes of the formula (4) which already contain a group of the formula (3) in the radical D, or the two groups -N ( R) contain H, and these are acylated together. If there are groups capable of metal complex formation in the reactive dyes produced, the reactive dyes can also be subsequently metallized.
  • Dyes of the formula (4) in which D is the remainder of a mono- or disazo dye are preferably used as starting materials.
  • the reactive dyes of the formula (1) of all classes of dyes can be prepared in a manner known per se or analogously to known procedures by starting from precursors or intermediates for dyes which contain fiber-reactive radicals of the formula (3), or these fiber-reactive radicals in introduces suitable intermediate products with a dye character.
  • acylation of the dyes of the formula (4) or of the dye precursors with the acyl halides of the formula (5) is carried out by methods known per se, preferably in aqueous solution or suspension and in the presence of alkaline, acid-binding agents, e.g. aqueous alkali metal hydroxides, carbonates or bicarbonates.
  • Another conversion reaction which can be connected to the synthesis is, for example, that a reactive dye of the formula (1), in which the rest of the formula (3) is an a, ß-dibromopropionyl amino residue, with hydrogen halide-releasing agents such as sodium hydroxide , treated so that the a, ß-dibromopropionyl group is converted into the a-bromoacryloyl group.
  • a reactive dye of the formula (1) in which the rest of the formula (3) is an a, ß-dibromopropionyl amino residue
  • hydrogen halide-releasing agents such as sodium hydroxide
  • Dyes of the following structure types are particularly suitable as amino dyes: wherein acyl is, for example, acetyl or optionally substituted benzoyl and B is -SO 3 H or
  • Cu (1: 1 complex) or Cr and Co (1: 2 complex) are preferred as the metal atom; Cr and Co complex can contain the azo compound of the above formula once or twice, ie they can be symmetrical or with any other Ligand groups have an asymmetrical structure.
  • the condensed rings indicated by dashed lines represent alternative naphthalene systems.
  • Pc represents the Cu or Ni phthalocyanine residue.
  • the total number of substituents on the Pc framework is 4.
  • the dyes of the formulas given above can be further substituted in the alkyl or aryl radicals, in particular by the substituents mentioned in the explanation of D in formula (1).
  • azo dyes of the formula (2) are particularly important azo dyes of the formula (2): and wherein K is the rest of a coupling component of the benzene, naphthalene or heterocyclic series, acyl is a low molecular weight, aliphatic acyl radical containing at most 3 carbon atoms or an aromatic radical containing at most 8 carbon atoms, and R is the meanings given in the explanation of formula (2) has, as well as the metal complex azo dyes of the formulas wherein R and acyl have the meanings given above and Me stands for Cu, Cr or Co.
  • the diazo component or the coupling component must have an acylatable amino group.
  • the intermediate products containing a diazotizable amino group are generally diazotized by the action of nitrous acid in aqueous mineral acid solution at low temperature, and the coupling at weakly acidic, neutral to weakly alkaline pH values.
  • Suitable acylating agents which contain a reactive radical in addition to the acylating site are, in particular, the halides or anhydrides of organic acids which contain easily exchangeable atoms or groups of atoms.
  • reactive compounds obtainable via corresponding methylols according to Einhorn, such as e.g. 1-amino-3-chloro-acetylaminomethyl-benzene-6-sulfonic acid.
  • acylations with the fiber-reactive acylating agents are expediently carried out using acid-binding agents, such as sodium carbonate or sodium hydroxide, and under such conditions that exchangeable halogen atoms, unsaturated bonds or the like remain in the reactive radical in the finished product, i.e. e.g. in organic solvents or at relatively low temperatures in an aqueous medium.
  • acid-binding agents such as sodium carbonate or sodium hydroxide
  • the following dyes are very particularly preferably used alone or in any possible combination in the process according to the invention: 1: 2 chromium mixed complex of the dyes of the formulas such as
  • dyeing or printing is carried out in an aqueous medium.
  • the design is such that the reactive dyes of the formula (1) are applied at a temperature between 15 and 100 ° C., in particular between 20 and 80 ° C., and are fixed on the fiber material by means of vapors in the presence of alkaline agents.
  • the method according to the invention is used for the production of dyeings and prints of mixed fibers from cellulose-containing fiber materials and silk.
  • Suitable cellulose-containing fiber materials are, for example, natural cellulose fiber, such as cotton, linen and hemp, as well as cellulose and regenerated cellulose. Mixtures of different cellulose fibers are also suitable, e.g. Cotton and linen or cotton and viscose.
  • the silk used is not only natural or cultivated silk (mulberry silk, Bombyx mori) but also the various wild silk, especially Tussah silk, also Eri and Fagara silk, Nester silk, Senegal silk, Muga silk, and shell and spider silk Consider.
  • the textile material mentioned can be in a wide variety of processing forms, e.g. as fiber, yarn, woven or knitted fabric.
  • all ratios of the mixed fiber i.e. all ratios of the proportion of cellulose-containing fiber, in particular viscose, and the proportion of silk are dyed or printed, e.g. a silk content of 5 to 95 percent by weight.
  • Mixed fibers with a silk content of 5 to 70 percent by weight, in particular 5 to 40 percent by weight, of silk are preferred.
  • Mixed fibers with a share of 5 to 15 percent by weight silk are also interesting.
  • mixed fibers are also lineni-cotton / silk blends and cotton / viscose / silk blends, the proportion of silk corresponding to the weight percentages mentioned.
  • the process according to the invention is characterized in that the mixed fiber is impregnated or padded with a dye solution or suspension, the liquor absorption being between 50 and 120 percent by weight, in particular between 50 and 80 percent by weight.
  • the padding liquor can already contain the necessary amount of fixing alkali.
  • the padding liquor preferably contains no fixing alkali.
  • the material can, for example, be dried as a post-treatment to a residual moisture of about 5 to 20, in particular 5 to 15 percent by weight, and then impregnated again with a liquor which contains the fixing alkali and this is followed by the fixation by steaming the goods.
  • a printing paste comprising, in addition to one or more of said reactive dyes, at least one alkali-acting agent such as Na 2 C0 3, NaHCO 3, CH 3 COONa, optionally a solubilizer, such as urea, E-caprolactam , Dicyan diamid, a thickener, in particular alginates, such as sodium alginate, and emulsions or half-emulsions and optionally an oxidizing agent, such as the sodium salt of m-nitrobenzenesulfonic acid, applied to the fiber material.
  • alkali-acting agent such as Na 2 C0 3, NaHCO 3, CH 3 COONa
  • a solubilizer such as urea, E-caprolactam , Dicyan diamid
  • a thickener in particular alginates, such as sodium alginate, and emulsions or half-emulsions and optionally an oxidizing agent, such as the sodium salt of m-nitrobenzenesulfonic acid,
  • the amount of fixing salt depends, for example, on the type and number of fiber-reactive residues. An amount of 30 to 90 g, in particular 50-70 g of fixing alkali per kg of printing paste has proven to be favorable. A quantity of 0 to 200 g, for example urea, per kg of printing paste is used as the solubilizer. A 5% alginate thickening with about 500 g per kg of printing paste has proven to be advantageous as a thickening agent. The amount of the oxidizing agent is between 10 and 20 g per kg of printing paste. After printing, the goods are steamed, if necessary after drying, to fix the dyes on the fiber.
  • a particularly preferred embodiment of the method according to the invention is characterized in that the mixed fiber is impregnated with a liquor which contains the dye solution or suspension, so that the liquor absorption is 50 to 80 percent by weight, then the goods up to a residual moisture content of 5 to 15 Weight percent dries, for example between 70 and 150 ° C. then the product is impregnated with a liquor which contains the fixing alkali, so that the liquor absorption is 50 to 80 percent by weight, and then the goods are steamed.
  • the liquor ratio of the padding liquor with which the reactive dyes of the formula (1) are applied to the fiber material is preferably 1: 0.5 to 1: 1.2, in particular 1: 0.5 to 1: 0.8.
  • the order of the fleet is carried out at a temperature between 15 and 100 ° C, in particular between 20 and 80 0 C and particularly preferably between 20 and 30 ° C.
  • Alkali metal hydroxides such as, for example, have been found to be fixative alkali which can be used in the process according to the invention.
  • NaOH, KOH and LiOH alkali carbonates such as e.g. Sodium carbonate and potassium carbonate and alkali hydrogen carbonates, e.g. Sodium bicarbonate and potassium bicarbonate, as well as trisodium phosphate and disodium phosphate, optionally together with neutral salts, e.g. Sodium chloride, proved to be suitable.
  • a mixture of viscose silk has proven to be particularly suitable as a mixed fiber.
  • the pH of the liquor is between 8.5 and 14.
  • the pH of this liquor is between 8.5 and 14.
  • a temperature between 100 and 220 ° C, in particular 100 'to 105 C in saturated steam, or 150 ° to 190 0 C in a hot-water vapor atmosphere, based on a pressure of 1 bar proven to be particularly advantageous.
  • the steaming time is 30 seconds to 20 minutes, in particular 60 seconds to 3 minutes.
  • the dyes are used in amounts of about 0.1 to 10%, depending on the desired depth of color.
  • the dyes used in the process according to the invention are either in the form of their free acid or preferably as their salts.
  • suitable salts are the alkali, alkaline earth or ammonium salts or the salts of an organic amine.
  • suitable salts include the sodium, lithium, potassium or ammonium salts or the salt of triethanolamine.
  • the dyeings and prints are rinsed with cold and hot water, if appropriate with the addition of a dispersing agent and promoting the diffusion of the unfixed portions.
  • a preferred embodiment is characterized in that the colored or printed Goods are washed in an aqueous washing liquor at a pH of 8.5 to 9 and elevated temperature, preferably 70 to 85 ° C., optionally in the presence of a nonionic detergent.
  • the dyeings and prints produced with the reactive dyes used according to the invention are distinguished by very good tone-on-tone nuances on the goods. High fixation rates and a very good build-up are achieved, and the dyeings and prints have good general fastness properties, in particular good light fastness properties and very good wet fastness properties.
  • the dye liquors and printing pastes can contain the generally customary additives, for example the aqueous solutions of inorganic salts, such as e.g. of alkali chlorides or alkali sulfates, urea, thickeners such as e.g. Alginate thickeners, water-soluble cellulose alkyl ethers as well as dispersants, leveling agents and migration inhibitors, also sodium m-nitrobenzenesulfonate and as further thickeners, e.g. Methyl cellulose, starch ether or emulsion thickeners, preferably an alginate, e.g. Sodium alginate and wetting agents.
  • inorganic salts such as e.g. of alkali chlorides or alkali sulfates, urea
  • thickeners such as e.g. Alginate thickeners, water-soluble cellulose alkyl ethers as well as dispersants, leveling agents and migration inhibitors, also sodium m-nitro
  • the following examples serve to illustrate the invention.
  • the parts are parts by weight and the percentages are percentages by weight.
  • the temperatures are given in degrees Celsius.
  • the relationship between parts by weight and parts by volume is the same as that between grams and cubic centimeters.
  • the amounts of dye given relate to commercially available dye.
  • a level gray coloration is obtained.
  • 40 g / l of the dye in the form of the free acid of the formula corresponds to 10 g / l of a migration inhibitor based on a polyacrylic acid derivative, 2 g / l of the sodium salt of m-nitrobenzenesulfonic acid and 2 g / l of a wetting agent.
  • the liquor is applied at a temperature of 25 °.
  • the mixed fabric is then dried at 120 ° for 40 seconds until a residual moisture of approx. 5 to 15 percent by weight remains on the goods.
  • the mixed fabric is impregnated on the pad with a squeezing effect of 75% at 25 ° with a liquor of the following composition: 200 g / l sodium chloride 15 ml / l of an aqueous sodium hydroxide solution with a density of 1.331 at 15 °.
  • the mixed fabric is then steamed in saturated steam at 102 ° for 60 seconds. Then it is rinsed cold and hot, soaped at the boil for 5 minutes with a nonionic detergent, rinsed again and dried. A red dyeing of the mixed fabric is obtained, which is excellently colored tone-on-tone.
  • a level gray coloration is obtained.
  • Example 14 If the procedure described in Example 14 is followed, but instead of the dyestuff of the formula (103), the following dyestuffs are used in the stated amounts, and a fabric made of 53% by weight of viscose, 12% by weight of silk and 35% by weight of cotton is used as the mixed fabric, dyeings are obtained in the specified color, with all types of fibers, cotton, viscose and silk, dyed in tone.
  • the following dyestuffs are used in the stated amounts, and a fabric made of 53% by weight of viscose, 12% by weight of silk and 35% by weight of cotton is used as the mixed fabric, dyeings are obtained in the specified color, with all types of fibers, cotton, viscose and silk, dyed in tone.
  • a mixed fabric of 88 percent viscose and 12 percent silk is printed with an order quantity of 100 gim 2 with a printing paste of the following composition: Strips of approx. 4 cm width are printed on the blended fabric using a flat template. The prints are then dried for 5 minutes at 100 ° and steamed for 20 minutes in saturated steam at 100-102 °, rinsed thoroughly with cold water and then treated for 5 minutes at 50 ° with a dye-affine auxiliary based on a polyglycol ether and an aliphatic amine in order to bleed to prevent unprinted areas with unfixed dye. This treatment is repeated on a fresh bath, but with the addition of 1 ml / l of a 25% aqueous ammonia solution for 5 minutes at 80 °. It is then rinsed warm and cold and then dried. A print of a yellow shade is obtained on the blended fabric, which is printed well tone-on-tone.

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  • Textile Engineering (AREA)
  • Coloring (AREA)
EP19900810694 1989-09-22 1990-09-13 Procédé de teinture ou d'impression de fibres mélangées contenant des fibres de cellulose et de la soie Ceased EP0419413A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH3445/89 1989-09-22
CH344589 1989-09-22

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EP0419413A1 true EP0419413A1 (fr) 1991-03-27

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Cited By (1)

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CN101418132B (zh) * 2008-11-11 2012-10-10 天津德凯化工股份有限公司 一种毛用紫色活性染料及其制备方法

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EP0726296B1 (fr) * 1995-02-10 2001-08-16 Ciba SC Holding AG Colorants azoiques
CN101585974B (zh) * 2008-12-12 2013-05-08 天津德凯化工股份有限公司 一种毛用活性染料艳蓝的制备方法
CN101481524A (zh) * 2008-12-12 2009-07-15 天津市德凯化工有限公司 一种活性红3g染料的制备方法
CN101735657B (zh) * 2009-11-16 2013-03-20 天津德凯化工股份有限公司 一种紫色毛用活性染料的制备方法
CN101705014B (zh) * 2009-11-16 2012-09-05 天津德凯化工股份有限公司 一种毛用橙色活性染料及其制备方法
CN101705015B (zh) * 2009-11-16 2012-09-05 天津德凯化工股份有限公司 一种橙色活性染料及其制备方法
CN101705010B (zh) * 2009-11-16 2013-08-14 天津德凯化工股份有限公司 一种毛用紫色活性染料
CN101723863B (zh) * 2009-11-16 2012-09-05 天津德凯化工股份有限公司 一种紫色活性染料的制备方法
CN101704770B (zh) * 2009-11-16 2012-09-05 天津德凯化工股份有限公司 紫色活性染料的制备方法
CN101705018B (zh) * 2009-11-16 2012-10-10 天津德凯化工股份有限公司 一种毛用橙色活性染料
CN103711008B (zh) * 2013-12-24 2015-07-01 淄博大染坊丝绸集团有限公司 丝棉交织服装面料半料染色工艺

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ES2053804T3 (es) * 1987-09-21 1994-08-01 Ciba Geigy Ag Procedimiento para teñir o estampar materiales de fibras poliamidicas naturales o sinteticas con colorantes reactivos.

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GB875163A (en) * 1959-09-28 1961-08-16 Ici Ltd Dyeing process
DE1919597A1 (de) * 1968-04-17 1969-10-30 Ici Ltd Faerbeverfahren
FR2006388A7 (fr) * 1968-04-17 1969-12-26 Ici Ltd
EP0202436A2 (fr) * 1985-04-06 1986-11-26 Hoechst Aktiengesellschaft Procédé de teinture ou d'impression de fibres de cellulose ou de fibres mixtes de cellulose

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CN101418132B (zh) * 2008-11-11 2012-10-10 天津德凯化工股份有限公司 一种毛用紫色活性染料及其制备方法

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