EP0509397A1 - Procédé de teinture de matériaux fibreux contenant de la cellulose modifié avec des polymères basiques, contenant de l'azote, avec des colorants anioniques et le matériau fibreux cellulosique modifié en lui même - Google Patents

Procédé de teinture de matériaux fibreux contenant de la cellulose modifié avec des polymères basiques, contenant de l'azote, avec des colorants anioniques et le matériau fibreux cellulosique modifié en lui même Download PDF

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Publication number
EP0509397A1
EP0509397A1 EP92106157A EP92106157A EP0509397A1 EP 0509397 A1 EP0509397 A1 EP 0509397A1 EP 92106157 A EP92106157 A EP 92106157A EP 92106157 A EP92106157 A EP 92106157A EP 0509397 A1 EP0509397 A1 EP 0509397A1
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Prior art keywords
hydrogen
methyl
carbon atoms
cellulose fiber
grafted
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German (de)
English (en)
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EP0509397B1 (fr
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Jörg Dr. Dannheim
Karl-Heinz Dr. Keil
Thomas Dr. Martini
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Hoechst AG
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Hoechst AG
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
    • D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
    • D06M14/20—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin
    • D06M14/22—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin of vegetal origin, e.g. cellulose or derivatives thereof
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
    • D06M14/02—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin
    • D06M14/04—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin of vegetal origin, e.g. cellulose or derivatives thereof
    • 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
    • D06P3/6008—Natural or regenerated cellulose using acid 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
    • 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
    • D06P3/66—Natural or regenerated cellulose using reactive dyes

Definitions

  • Textile materials such as fabrics, knitted fabrics, yarns and threads, which consist of cellulose fibers or a mixture of cellulose fibers with other fibers, are dyed using anionic dyes, in particular anionic fiber-reactive dyes, according to the usual application techniques, for example in such a way that , in particular when using fiber-reactive dyes, the dyeing process in the presence of an alkali, such as sodium hydroxide solution, sodium carbonate and sodium silicate, and in the presence of electrolytes, such as sodium chloride or sodium sulfate, at elevated temperatures, such as at 60 ° C. Continuous and semi-continuous dyeing methods are also used for this purpose, such as the pad-steam method or the pad-cold retention method.
  • anionic dyes in particular anionic fiber-reactive dyes
  • the textile material is first padded with the aqueous liquor containing the dye (fiber-reactive dye) and the alkali required for fixation is applied to the textile material in a later, separate impregnation step.
  • Suitable alkali are preferably sodium hydroxide solution, potassium hydroxide solution, sodium carbonate (in aqueous solution) and aqueous water glass solutions.
  • the fiber materials dyed in this way are distinguished by a high brilliance of the coloring and by very good fastness to use, such as, for example, wet fastness, rubbing fastness, cooking fastness and light fastness.
  • the present invention therefore relates to a process for dyeing cellulose fiber materials with anionic dyes, in particular fiber-reactive dyes, which is characterized in that the dyeing is carried out using low-electrolyte and alkali-free dyeing liquors and a modified cellulose fiber described below is used as the cellulose fiber material.
  • Modified cellulose fiber materials which can be used in the dyeing process according to the invention are cellulose fiber materials onto which a polymer has been grafted which contains at least one polymerizable, N-containing, basic monomer from the group of the general formulas (1), (1A), (2 ) and (2A) as building block contains:
  • Monovalent anions Y (-) are, for example, monovalent residues of a mineral acid, sulfonic acid or carboxylic acid or a residue of a polybasic mineral acid, sulfonic acid or carboxylic acid equivalent to a monovalent anion.
  • Monovalent anions Y (-) are, for example, the nitrate, bisulfate, benzenesulfonate, fluoride, chloride, bromide, iodide, acetate or propionate anion or the anionic radical of another aliphatic or aromatic carboxylic acid.
  • a part of a multivalent anion equivalent to a monovalent anion is, for example, half the equivalent of a sulfate anion or the third equivalent of a phosphate anion.
  • Y (-) is a halogen anion, such as the bromide or iodide anion and especially the chloride anion.
  • Alkyl radicals in the above formulas are, for example, the methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec.-butyl, iso-butyl, n-pentyl and n-hexyl radical .
  • Cycloalkyl radicals are, for example, the cyclopentyl, cyclohexyl and cycloheptyl radical, preferably the cyclohexyl radical thereof.
  • Hydroxyalkyl radicals are, for example, 2-hydroxyethyl, 2-hydroxy-n-propyl, 3-hydroxy'-n-propyl, 2-, 3- or 4-hydroxy-n-butyl and 2-methyl-3 -hydroxy-n-propyl radical. If R1 and R2 or R6 and R7 together with the N atom to which they are attached form a 5- or 6-membered, saturated or unsaturated, optionally interrupted by heteroatoms, these are, for example, the pyrrolidinyl, piperidino -, Pyrrolyl, pyridinyl-piperazinyl, morpholino or thiomorpholino radical.
  • Phenylalkyl radicals in which the alkyl radical can be straight-chain or branched are, for example, the benzyl, phenethyl, 3-phenyl-n-propyl, 2-phenyl-n-propyl, 3-phenyl-n-propyl, 3-phenyl-n-butyl or 4-phenyl-n-butyl radical, preferably the benzyl radical thereof.
  • Examples of a radical of the formula - (CH2-CH2-O) p -phenyl are, for example, the ⁇ - (phenoxy) ethyl radical or radicals in which p represents the number 2 or 4.
  • the abovementioned monomers are particularly preferred in the form of their quaternized compounds corresponding to the general formula (1A), the three alkyl radicals on the quaternary nitrogen atom preferably having the same meaning.
  • Y (-) has one of the meanings mentioned above and is preferably the chloride anion.
  • radical R7 is an allyl radical, preferably the dimethylallyl radical, are to be mentioned as preferred.
  • Substituents in the radical R 11 are, for example, alkyl radicals of 1 to 4 carbon atoms and hydroxyalkyl radicals of 2 to 4 carbon atoms.
  • R 12 is preferably a hydrogen atom.
  • the 5-membered, heterocyclic, saturated or unsaturated radicals representing the radical R11 are, for example, the imidazolyl, imidazolinyl, pyrrolyl, pyrrolinyl, pyrrolidinyl and the indolyl radical.
  • Five-membered ring compounds of the general formula (5) are, for example, N-vinyl-imidazole, 1-vinyl-2-imidazoline, 2-vinyl-4-methyl-imidazoline, 2-vinyl-5-methyl-imidazoline, 1-vinyl-2 -methyl imidazole, 1-vinyl-4- ( ⁇ -hydroxyethyl) imidazole, N-vinyl pyrrole, 2-isopropenyl-2-imidazoline and 1-vinyl-2,4-dimethyl-imidazole.
  • Residues R11, the Six-membered heterocyclic, saturated or unsaturated radicals are, for example, the pyrridinyl or quinolinyl radical.
  • Six-membered heterocyclic compounds of the general formula (5) are, for example, 2-vinyl-pyridine, 3-vinyl-pyridine, 4-vinyl-pyridine, 3-isopropenyl-pyridine, 2-vinyl-quinoline, 2-methyl-3-vinyl- 8-hydroxy-quinoline, 2-vinyl-quinoline, 2-methyl-3-vinyl-isoquinoline, 1-methyl-5-vinyl-isoquinoline and 2-isopropenyl-quinoline.
  • vinyl pyridine and its derivatives are particularly preferred.
  • the polymer grafted onto the cellulose fiber material can be constructed from monomeric building blocks of one or more compounds of the formulas (1), (1A), (2), (2A) and / or (5) mentioned above. It can also contain other polymerizable monomers.
  • the polymer grafted onto the cellulose fiber material according to the invention contains, for example, 20 to 100 mol%, preferably 40 to 100 mol% and particularly preferably 80 to 100 mol%, of one or more compounds of the above formulas.
  • the division between the monomers of the above formulas is arbitrary.
  • the grafted-on polymer contains only one of the compounds of the above formulas, i.e. a cellulose fiber material with a grafted-on homopolymer is preferred.
  • Copolymers which may be grafted onto the cellulose fiber material are those which, in addition to the above-mentioned monomers of the general formulas (1), (1A), (2), (2A) and / or (5), are one or more comonomers corresponding to those
  • the following general formulas (6) and (7) contain:
  • Monomers of the general formula (6) are, for example, acrylamide and methacrylamide.
  • Compounds of the general formula (7) are, for example, the (C1-C6) alkyl esters, in particular the methyl and ethyl esters, acrylic and methacrylic acid.
  • the grafting of the mono- or copolymer onto the cellulose fiber is carried out in such a way that one or more monomers of the formulas (1), (1A), (2), (2A) and / or (5) optionally in the presence of one or more monomers of the general formula (6) and / or (7) are polymerized.
  • the polymerization or copolymerization on the fiber takes place in a suitable solvent.
  • a suitable solvent such are in particular water in a mixture with a water-miscible solvent which is inert to the monomers.
  • Such solvents are, for example, lower alcohols, such as alkanols of 1 to 5 carbon atoms, for example methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, glycols and diols, such as, for example, ethylene glycol, propylene glycol and propane-1 , 3-diol, di- and polyglycols, such as, for example, diethylene glycol and triethylene glycol, glycol ethers, such as, for example, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono n-butyl ether, ethylene glycol dimethyl ether and ethylene glycol diethyl ether, and also ketones, such as acetone and methyl ethyl ketone.
  • the homopolymerization and the copolymerization in the presence of the cellulose fiber material can also be carried out in a mixture of different solvents which contains water. If one or more components are used in the form of aqueous solutions, a further addition of water is generally not necessary. Water in a mixture of alcohols, such as alkanols, in particular those having 1 to 4 carbon atoms, and in a mixture with diols and / or glycols is preferred. It may be expedient to add organic solvent or solvent mixture once or in particular several times during the homo- or copolymerization.
  • the pH is adjusted to values from 3 to 11.5, preferably from 3 to 8.5.
  • An acid preferably an organic acid, in particular formic acid, acetic acid, glycolic acid and / or citric acid, is generally used for this.
  • the homo- and copolymerization is carried out in the presence of the cellulose fiber material at room temperature (10 to 30 ° C) or at a higher temperature of up to about 160 ° C, but usually at a temperature between 40 and 100 ° C and preferably between 60 and 90 ° C, particularly preferably between 65 to 85 ° C, performed.
  • Suitable polymerization initiators such as, for example, radical-forming substances, are used for this in the usual way.
  • the action of high-energy radiation, such as UV rays, and also microwaves and the action of ultrasound can also serve to start the polymerization.
  • Free radical initiators are, for example, benzoyl peroxide, tert-butyl hydroperoxide, cumene peroxide, methyl ethyl ketone peroxide, lauryl peroxide, tert-butyl perbenzoate, di-tert-butyl perphthalate, azodiisobutyronitrile, 2,2'-azobis (2 , 4-dimethylvaleronitrile), 2-phenyl-azo-2,4-dimethyl-4-methoxy-valeronitrile, 2-cyano-2-propyl-azo-formamide, azodiisobutyramide, dimethyl-, diethyl- or di-n-butyl- azobismethylvalerate, tert-butyl perneodecanoate, di-isononanoyl peroxide, tert-amyl perpivalate, Di-2-ethylhexyl peroxydicarbonate, dilauroyl per
  • the polymerization or copolymerization or the grafting in the absence of oxygen. This can be done in a manner known per se by purging or passing through an inert gas, such as nitrogen.
  • the monomer components are used in amounts such that the polymer grafted onto the cellulose contains at least 20 mol%, preferably at least 40 mol% and particularly preferably at least 80 mol% of one or more compounds of the formulas (1), (1A), ( 2), (2A) and / or (5) in copolymerized form.
  • the grafting can be carried out in such a way that the cellulose fiber material to be grafted is introduced into the polymerization vessel together with the solution of the monomer (s) and the homopolymerization or copolymerization is carried out.
  • the homo- or copolymerization is usually complete after about 0.5 to 4 hours, in many cases after 0.5 to 2.5 hours.
  • the cellulose fiber material is then removed from the polymerization container, freed from adhering liquid, for example by squeezing, rinsed with water and dried.
  • the grafting of the cellulose fiber can also be carried out in such a way that the monomer solution is applied to the cellulose fiber material by padding, slapping, soaking or spraying, and then the homo- or copolymerization at normal temperature or elevated temperature, expediently by the action of high-energy rays or ultrasound is triggered.
  • the cellulose fiber material is then stored in a moist condition for a further 2 to 36 hours, preferably 10 to 24 hours, and is then dried, after rinsing, if necessary.
  • Cellulose fiber materials which are suitable for modification in the manner according to the invention are, for example, cotton and rayon as well as the linen, jute and ramie fibers and regenerated cellulose fibers, preferably the cotton fiber.
  • the modified cellulose fiber materials can also be present as a proportion in blended fabrics, such as blended fabrics of such modified cellulose fibers with polyester fibers.
  • the modification of the cellulose fiber according to the invention can take place in the blended fabric itself and in all processing states, such as yarn, flake, sliver and piece goods.
  • Cellulose fiber material has already been modified by polymerization according to the specification of US Pat. No. 4,464,523 using N, N-diallyl-N, N-dialkylammonium halides as monomers, such modified cellulose derivatives being used as auxiliaries in shampoos and other hair treatment agents.
  • modified cellulose derivatives being used as auxiliaries in shampoos and other hair treatment agents.
  • the use of cellulose fiber materials modified in this way, such as cotton modified in this way, as a substrate for dyeing with anionic, in particular fiber-reactive, dyes is not yet known.
  • the modification by grafting on the polymers, including copolymers, of compounds of the general formulas (1), (1A), (2) and / or (2A) is new.
  • the present invention thus also relates to cellulose fiber materials which, in the manner according to the invention, are grafted onto the polymer Compounds of the general formula (1) and / or (2) or their quaternized derivatives have been modified.
  • the dyeing of cellulose fiber materials modified in this way in the manner according to the invention is carried out analogously to the known dyeing methods for dyeing cellulose fiber materials using anionic dyes, in particular anionic fiber-reactive dyes, and using the temperature ranges and customary amounts of dye known for this purpose, but with the exception according to the invention that for the dye baths and padding liquors of the dyeing process according to the invention, an addition of alkaline compounds, as are usually used for fixing fiber-reactive dyes, such as sodium carbonate, potassium carbonate, sodium hydroxide solution and water glass, can be excluded, and furthermore the usual addition of electrolyte salts, which in particular the migration of the Dye should increase on the fiber, not or only to a small extent, ie up to a maximum of 10 g per liter of dye bath or dye liquor is required.
  • the dyeing process according to the invention is accordingly carried out within a pH range from 3 to 7.5, preferably from 4.5 to 7.
  • Dyeing processes which can be used according to the invention are, for example, the various exhaust processes, such as dyeing on the jigger and on the reel runner or dyeing from a long or short liquor, dyeing in jet dyeing machines, dyeing using the pad-cold-dwell method or after a block hot steam fixing process.
  • the pull-out process can be carried out in the usual liquor ratio of 1: 3 to 1:20.
  • the dyeing temperature can be between 30 and 90 ° C, preferably at temperatures below 60 ° C; As can be seen from the above-mentioned application of the pad-cold residence method according to the invention, dyeing is also advantageously possible at room temperature (10 to 30 ° C.).
  • auxiliaries such as surfactants (wetting agents), urea and leveling aids or auxiliaries, which improve the solubility of dyes in the concentrated padding liquors, such as condensation products of formaldehyde and optionally alkyl-substituted naphthalenesulfonic acids.
  • anionic dyes which have one or more sulfo and / or carboxy groups and which can optionally contain fiber-reactive groups are suitable for the dyeing methods according to the invention. They can belong to the class of azo dyes, copper complex, cobalt complex and chromium complex azo dyes, copper and nickel phthalocyanine dyes, anthraquinone, copper formazane and triphendioxazine dyes. Such dyes have been described in numerous literature and are well known to those skilled in the art.
  • the dyeings of the modified cellulose fiber materials obtainable in the manner according to the invention do not require any further aftertreatment after removal from the dyebath or after the dye has been fixed on the substrate, in particular no complicated aftertreatment process including washing. As a rule, it is sufficient to rinse the colored substrate once or several times with cold, warm or hot water, which may optionally contain a nonionic wetting agent. A final boiling treatment of the dyed substrate with a washing solution to improve the fastness properties is not necessary.
  • the cotton cloth is then removed from the reaction flask, squeezed off, rinsed twice with 500 ml of water each time, squeezed out in between and then dried at 100 ° C. for 5 minutes.
  • the absorption of polymer is 5.3%.
  • a pH of 8.5 to 9.0 is set with 231 g of glacial acetic acid. 960 g of water and 2060 mg of 2,2'-azobis (2-amidino-propane) dihydrochloride as initiator are added; the flask is then evacuated three times, rendered inert with nitrogen and heated to 79 to 80 ° C.
  • the active substance concentration of polymer is 25%.
  • the K value of a 1% aqueous solution is: 112600.
  • Example 2 When Example 2 is repeated, the cotton cloth is replaced by a 3.4 g heavy, 8 x 47 cm large cellulose cloth. The absorption of polymer is 2.95%.
  • Example 3 When Example 3 is repeated, the cotton cloth is replaced by a 5.7 g, equally large cloth made from a 65:35% polyester / cotton blended fabric. The absorption of polymer is 3.4%.
  • a solution is released in a 3 liter three-necked flask equipped with an anchor stirrer, gas inlet tube and reflux condenser 200 g of distilled water, 56.7 g of table salt, 287 mg of ethylenediaminetetraacetic acid disodium salt, 250 g ethanol and 1210 g of dimethyl-diallylammonium chloride as 61% aqueous solution.
  • a solution 200 ml water, 18.1 g of table salt, 206, 18 g dimethylaminopropyl methacrylamide, 63.9 g of ethanol and 81.4 mg disodium salt of ethylenediaminetetraacetic acid is adjusted to a pH of 8.5 to 9.0 with glacial acetic acid and applied to a cotton cloth via a padder and squeezed off.
  • the liquor intake after squeezing is 114.4%.
  • the damp cloth is subjected to a microwave treatment (30 seconds with 90 watts and then 4 times 30 seconds with 720 watts). Thereafter, the damp cloth is left for 24 hours at room temperature and then dried for 5 minutes at 100 ° C. The absorption of polymer is 29.5%.
  • Example 6 The monomer solution given in Example 6 is applied to a cotton cloth and squeezed off in the manner given in Example 6.
  • the damp cloth is exposed to UV radiation to trigger the polymerization and grafting.
  • the aftertreatment of the cloth is carried out as indicated in Example 6.
  • the absorption of polymer is 30.8%.
  • the polymer solution obtained is 38% (to determine the content, a sample is heated at 120 ° C. for 2 hours at a pressure of 200 mbar). The viscosity of the solution is measured in a DIN cup (nozzle diameter 6 mm) for 44.6 seconds. The cloth is removed and treated as in Example 1. The absorption of polymer is 4.7%.
  • a cotton fabric modified according to Example 1 is first treated for 15 minutes by boiling in water and then dried. This fabric is then dyed according to a pad cold-dyeing process.
  • the fabric sealed with the dye solution is wound up on a dock, wrapped in a plastic sheet and left at 20 ° C. for 16 hours and then rinsed with cold and hot water and dried.
  • a strong, uniformly colored orange coloration is obtained which has good general fastness properties, in particular good fastness to rubbing and light.
  • Example A an orange coloration with good general fastness properties, in particular good fastness to rubbing and light, is obtained.
  • a cotton fabric modified according to Example 1 is first boiled in water for 15 minutes and then dried and dyed according to a block-cold-dyeing process.
  • an aqueous dye solution containing 28.6 parts of a 50% electrolyte-containing (predominantly sodium chloride) dye powder of the dye of the formula in 1000 parts by volume contains 100 parts of urea and 3 parts of a commercially available nonionic wetting agent in solution, using a padder with a liquor absorption of 80%, based on the weight of the fabric, applied to the fabric at 20 ° C. That with this Tissue solution padded fabric is wound up on a dock, wrapped in a plastic sheet and left at 20 ° C for 16 hours and then rinsed with cold and hot water and dried.
  • a strong, uniformly colored bluish red coloration is obtained which has good general fastness properties, in particular good fastness to rubbing, washing and light.
  • a cotton fabric modified according to Example 1 is first treated for 15 minutes by boiling in water and then dried. This fabric is then treated with an aqueous dye solution containing 28.5 parts of a 50% electrolyte-containing (predominantly sodium chloride) dye powder of the known dye of the formula in 1000 parts by volume Contains 100 parts of urea and 3 parts of a commercially available nonionic wetting agent dissolved, using a padder with a liquor absorption of 80%, based on the weight of the fabric, at 20 ° C. The padded fabric is wound on a dock, wrapped in a plastic wrap and left at 20 ° C for 16 hours and then rinsed with cold and hot water and dried.
  • an aqueous dye solution containing 28.5 parts of a 50% electrolyte-containing (predominantly sodium chloride) dye powder of the known dye of the formula in 1000 parts by volume Contains 100 parts of urea and 3 parts of a commercially available nonionic wetting agent dissolved, using a padder with a liquor absorption
  • a strong, uniformly colored red dyeing is obtained which has good general fastness properties, in particular good fastness to rubbing and light.
  • Example D an orange coloration with good general fastness properties, in particular good fastness to rubbing and light, is obtained.
  • a cotton fabric modified according to Example 1 is first boiled in water for 15 minutes and then dried and dyed according to a block-cold-dyeing process.
  • an aqueous dye solution containing 28.6 parts of a 50% electrolyte-containing (predominantly sodium chloride) dye powder of the dye of the formula in 1000 parts by volume (which can be prepared in the usual manner from the diazo and coupling components shown in the formula), containing 100 parts of urea and 3 parts of a commercially available nonionic wetting agent, by means of a padder with a liquor absorption of 80%, based on the weight of the fabric, applied to the fabric at 20 ° C.
  • the fabric padded with this dye solution is wound onto a dock, wrapped in a plastic film and left at 20 ° C. for 16 hours and then rinsed with cold and hot water and dried.
  • a strong, uniformly colored orange-red dyeing is obtained which has good general fastness properties, in particular good fastness to rubbing, washing and light.
  • a cotton fabric modified according to Example 1 is first boiled in water for 15 minutes and then dried and then with an aqueous dye solution which contains 28.5 parts of the dye powder described in Example G, 100 parts of urea and 3 parts of a commercial dye in 1000 parts by volume contained nonionic wetting agent dissolved, with a liquor absorption of 80%, based on the weight of the fabric, padded at 20 ° C.
  • the padded fabric is wound on a dock, wrapped in a plastic wrap and left at 20 ° C for 16 hours and then rinsed with cold and hot water and dried.
  • a strong, uniformly colored yellow color is obtained which has good general fastness properties, in particular good fastness to rubbing, washing and light.
  • a cotton fabric modified in accordance with Example 9 is first boiled in water for 15 minutes and then dried. This fabric is then dyed according to a pad cold-dyeing process.
  • an aqueous dye solution containing 28.5 parts of the dye powder described in Example A, 100 parts of urea and 3 parts of a commercially available nonionic wetting agent dissolved in 1000 parts by volume, using a padder with a liquor absorption of 80%, based on the Weight of the fabric, applied to the fabric at 20 ° C.
  • the fabric sealed with the dye solution is wound onto a dock, wrapped in a plastic sheet and left at 20 ° C. for 16 hours and then rinsed with cold and hot water and dried.
  • a strong, uniformly colored orange coloration is obtained which has good general fastness properties, in particular good fastness to rubbing and light.
  • Example A an orange coloration with good general fastness properties, in particular good fastness to rubbing and light, is obtained.
  • a cotton fabric modified according to Example 9 is first boiled in water for 15 minutes and then dried and dyed according to a block-cold-dyeing process.
  • an aqueous dye solution which contains 28.6 parts of the dye powder described in Example C, 100 parts of urea and 3 parts of a commercially available nonionic wetting agent dissolved in 1000 parts by volume, using a padder with a liquor absorption of 80%, based on the Weight of the fabric, applied to the fabric at 20 ° C.
  • the fabric padded with this dye solution is wound onto a dock, wrapped in a plastic film and left at 20 ° C. for 16 hours and then rinsed with cold and hot water and dried.
  • a strong, uniformly colored bluish red coloration is obtained which has good general fastness properties, in particular good fastness to rubbing, washing and light.
  • a cotton fabric modified in accordance with Example 9 is first boiled in water for 15 minutes and then dried. This fabric is then treated with an aqueous dye solution which contains 28.5 parts of the in Contains dye powder described in Example D, 100 parts of urea and 3 parts of a commercially available nonionic wetting agent dissolved, padded at 20.degree. C. using a padding machine with a liquor absorption of 80%, based on the weight of the fabric.
  • the padded fabric is wound on a dock, wrapped in a plastic wrap and left at 20 ° C for 16 hours and then rinsed with cold and hot water and dried.
  • a strong, uniformly colored red dyeing is obtained which has good general fastness properties, in particular good fastness to rubbing and light.
  • Example D an orange coloration with good general fastness properties, in particular good fastness to rubbing and light, is obtained.
  • a cotton fabric modified according to Example 9 is first boiled in water for 15 minutes and then dried and dyed according to a block-cold-dyeing process.
  • an aqueous dye solution which contains 28.6 parts of the dye powder described in Example F, 100 parts of urea and 3 parts of a commercially available nonionic wetting agent dissolved in 1000 parts by volume, using a padder with a liquor absorption of 80%, based on the Weight of the fabric, at 20 ° C on the fabric upset.
  • the fabric padded with this dye solution is wound onto a dock, wrapped in a plastic film and left at 20 ° C. for 16 hours and then rinsed with cold and hot water and dried.
  • a strong, uniformly colored orange-red dyeing is obtained which has good general fastness properties, in particular good fastness to rubbing, washing and light.
  • a cotton fabric modified according to Example 9 is first boiled in water for 15 minutes and then dried and then with an aqueous dye solution containing 28.5 parts of the dye powder described in Example G, 100 parts of urea and 3 parts of a commercial dye in 1000 parts by volume contained nonionic wetting agent dissolved, with a liquor absorption of 80%, based on the weight of the fabric, padded at 20 ° C.
  • the padded fabric is wound on a dock, wrapped in a plastic wrap and left at 20 ° C for 16 hours and then rinsed with cold and hot water and dried.
  • a strong, uniformly colored yellow color is obtained which has good general fastness properties, in particular good fastness to rubbing, washing and light.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Coloring (AREA)
  • Graft Or Block Polymers (AREA)
EP92106157A 1991-04-15 1992-04-09 Procédé de teinture de matériau fibreux cellulosique modifié avec des polymères basiques contenant de l'azote avec des colorants anioniques réactifs, et le matériau fibreux cellulosique modifié en soi Expired - Lifetime EP0509397B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4112227 1991-04-15
DE4112227 1991-04-15

Publications (2)

Publication Number Publication Date
EP0509397A1 true EP0509397A1 (fr) 1992-10-21
EP0509397B1 EP0509397B1 (fr) 1997-03-12

Family

ID=6429594

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EP92106157A Expired - Lifetime EP0509397B1 (fr) 1991-04-15 1992-04-09 Procédé de teinture de matériau fibreux cellulosique modifié avec des polymères basiques contenant de l'azote avec des colorants anioniques réactifs, et le matériau fibreux cellulosique modifié en soi

Country Status (7)

Country Link
EP (1) EP0509397B1 (fr)
JP (1) JPH05140880A (fr)
KR (1) KR920020011A (fr)
BR (1) BR9201379A (fr)
DE (1) DE59208153D1 (fr)
TR (1) TR25952A (fr)
TW (1) TW201803B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0665311A1 (fr) * 1994-01-29 1995-08-02 Hoechst Aktiengesellschaft Fibres synthétiques cellulosiques aminées
DE4422758A1 (de) * 1994-06-29 1996-01-04 Hoechst Ag Aminierte Cellulose-Regeneratfasern
CN110041463A (zh) * 2018-12-28 2019-07-23 福建清源科技有限公司 一种改性罗望子胶聚合物及其制备方法和用途
GR1010528B (el) * 2022-05-09 2023-08-29 Ιδρυμα Τεχνολογιας Και Ερευνας / Ινστιτουτο Επιστημων Χημικης Μηχανικης (Ιτε / Ιεχμη), Μεθοδος βελτιωσης της βαφικης ικανοτητας σε βαμβακερα υφασματα

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013141222A1 (fr) * 2012-03-19 2013-09-26 Jsr株式会社 Procédé de formation d'un motif de réserve et composition de photoréserve
JP7079624B2 (ja) * 2018-03-07 2022-06-02 株式会社日本触媒 繊維材料捺染又は染色用組成物、捺染又は染色用の処理層を有する繊維材料の製造方法、ならびに捺染又は染色された繊維材料の製造方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3514385A (en) * 1966-07-19 1970-05-26 Du Pont Process for radiation grafting onto a partially swollen cellulosic substrate
EP0265768A2 (fr) * 1986-10-27 1988-05-04 National Starch and Chemical Investment Holding Corporation Traitement de tissu pour augmenter son affinité pour les colorants

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JPS5696972A (en) * 1979-12-28 1981-08-05 Toray Industries Enhancement of dyeing fastness
DE3709766A1 (de) * 1987-03-25 1988-10-06 Hoechst Ag Verfahren zum alkali-freien faerben mit reaktivfarbstoffen
DE3831464A1 (de) * 1988-09-16 1990-03-29 Hoechst Ag Verfahren zum alkali-freien faerben und bedrucken von cellulosefasern

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Publication number Priority date Publication date Assignee Title
US3514385A (en) * 1966-07-19 1970-05-26 Du Pont Process for radiation grafting onto a partially swollen cellulosic substrate
EP0265768A2 (fr) * 1986-10-27 1988-05-04 National Starch and Chemical Investment Holding Corporation Traitement de tissu pour augmenter son affinité pour les colorants

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 95, 28. Dezember 1981, Columbus, Ohio, US; abstract no. 221247, 'Improvement of colorfastness of textiles.' *
WORLD PATENTS INDEX Derwent Publications Ltd., London, GB; AN 68-11046Q & SU-A-193 020 (KAUSKANSKII DA) *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0665311A1 (fr) * 1994-01-29 1995-08-02 Hoechst Aktiengesellschaft Fibres synthétiques cellulosiques aminées
US5865858A (en) * 1994-01-29 1999-02-02 Hoechst Aktiengesellschaft Aminated cellulosic synthetic fibers
DE4422758A1 (de) * 1994-06-29 1996-01-04 Hoechst Ag Aminierte Cellulose-Regeneratfasern
CN110041463A (zh) * 2018-12-28 2019-07-23 福建清源科技有限公司 一种改性罗望子胶聚合物及其制备方法和用途
CN110041463B (zh) * 2018-12-28 2021-06-04 福建清源科技有限公司 一种改性罗望子胶聚合物及其制备方法和用途
GR1010528B (el) * 2022-05-09 2023-08-29 Ιδρυμα Τεχνολογιας Και Ερευνας / Ινστιτουτο Επιστημων Χημικης Μηχανικης (Ιτε / Ιεχμη), Μεθοδος βελτιωσης της βαφικης ικανοτητας σε βαμβακερα υφασματα

Also Published As

Publication number Publication date
KR920020011A (ko) 1992-11-20
JPH05140880A (ja) 1993-06-08
TR25952A (tr) 1993-11-01
BR9201379A (pt) 1992-12-01
TW201803B (fr) 1993-03-11
EP0509397B1 (fr) 1997-03-12
DE59208153D1 (de) 1997-04-17

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