EP0242324B1 - Procédé de teinture de fibres cellulosiques ayant une égalité de nuance entre les extrémités du tissu - Google Patents

Procédé de teinture de fibres cellulosiques ayant une égalité de nuance entre les extrémités du tissu Download PDF

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Publication number
EP0242324B1
EP0242324B1 EP87810172A EP87810172A EP0242324B1 EP 0242324 B1 EP0242324 B1 EP 0242324B1 EP 87810172 A EP87810172 A EP 87810172A EP 87810172 A EP87810172 A EP 87810172A EP 0242324 B1 EP0242324 B1 EP 0242324B1
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Prior art keywords
formula
process according
radical
dye
alkyl
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German (de)
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EP0242324A1 (fr
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Jean-Marie Sire
Peter Dr. Scheibli
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Novartis AG
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Ciba Geigy AG
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    • 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
    • D06P3/62—Natural or regenerated cellulose using direct 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
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/62—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/628—Compounds containing nitrogen
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6422—Compounds containing nitro or nitroso 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6426—Heterocyclic compounds
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6429—Compounds containing nitrogen bound to a six-membered aromatic carbocyclic ring
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl 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
    • 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

  • the present invention relates to a new process for dyeing textile cellulosic fibers with direct and / or reactive dyes according to the padding, padding or pad process by using an aqueous liquor which, in addition to at least one direct and / or reactive dye, is used contains a water-soluble, anionic, fiber-affine, colorless organic compound.
  • the padding, padding or pad process is a dyeing process known for cellulose fibers, which allows large amounts of wear and tear to be achieved by soaking or impregnating the fiber with the dye solution in a trough with the shortest liquor ratio and usually only passing through the pad once with a short dyeing time to dye textile fiber materials and then fix them.
  • Tailing / reversed tailing is the difference in strength and nuance between the beginning and the end of a game.
  • 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 dye depletion of the liquor is caused by the dye being drawn up during the padding process. Differences in strength and shade based on tailing occur particularly with dyes with medium to high substantivity, and very particularly often when coloring light shades.
  • Reversed 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 reversed tailing occur with dyes of low substantivity, especially when coloring dark shades.
  • the present invention relates to a new process for dyeing cellulose fibers at the same end, preferably in light shades.
  • the present invention thus relates to a process for dyeing cellulose fibers or cellulose-containing mixed fibers with direct and / or reactive dyes using the padding process, which is characterized in that an aqueous liquor containing at least one water-soluble direct and / or reactive dye and at least one water-soluble anionic, fiber-affine, colorless organic compound with an affinity factor A at a concentration of 0.2-0.3 g / l on mercerized cotton of 1.1 to 4, the factor A being the quotient of the concentration of the water-soluble, fiber-affine , colorless organic compound in a dye-free liquor before impregnation to the concentration of the water-soluble, fiber-affine, colorless organic compound in the dye-free squeezed liquor.
  • compounds are termed colorless if their absorption maximum lies outside the visible spectral range or their absorption is very low in the visible range.
  • the water-soluble, fiber-affine, colorless organic compound used in the process according to the invention is a compound with "dye character", i.e. the behavior of this compound under dyeing conditions corresponds to the behavior of a substantive dye, i.e. the compound has a certain substantivity for cellulose.
  • the fiber-affine, colorless organic compounds advantageously contain 1 to 6, preferably 1 to 4 acidic water-solubilizing groups, which are in particular carboxyl groups or especially sulfonic acid groups.
  • the water-soluble, fiber-affine, colorless organic compounds preferably contain no further ionic groups and no halogen-containing heterocycles of aromatic character, such as halotriazines.
  • the method according to the invention is suitable for all pure cellulose fibers, e.g. mercerized or leached or bleached cotton or cellulose, as well as for cellulose-containing mixed fibers, e.g. Polyester / cellulose blended fabrics, equally applicable, without being limited to certain direct or reactive dyes or certain fiber-reactive groups of the reactive dyes; It is also surprising that regardless of the concentration of the dyes, regardless of the electrolyte content or alkali, regardless of conventional dyeing aids (wetting agents) and regardless of the dipping time and the trough content, identical dyeings are obtained.
  • the direct dyes which can be used in the process according to the invention are the customary direct dyes, for example the "Direct Dyes” mentioned in Color Index, 3rd edition (1971) Volume 2 on pages 2005 to 2478.
  • Reactive dyes are understood to be the usual dyes that form a chemical bond with the cellulose, e.g. the "Reactive Dyes” listed in Color Index, Volume 3 (3rd edition, 1971) on pages 3391 to 3560 and in Volume 6 (revised 3rd edition, 1975) on Pages 6268 to 6345.
  • direct or reactive dyes with an affinity factor B for mercerized cotton at a concentration of 0.1 gram per liter of at least 1.1 are used in the process according to the invention, the affinity factor B being the quotient of the concentration of the dye in the original liquor without addition the water-soluble, fiber-affine, colorless organic compound to the concentration of the dye in the squeezed liquor.
  • dye mixtures are used in the process according to the invention, e.g. Mixtures of different reactive dyes or different direct dyes or mixtures of different direct and reactive dyes, at least one of the dyes used should have an affinity factor B of at least 1.1.
  • the determination of the affinity factor A for the water-soluble, fiber-affine, colorless organic compound or the determination of the affinity factor B for the direct or reactive dyes is carried out by measuring the concentration of the original liquor and the squeezed liquor by forming the ratio of the measured concentrations, ie
  • the concentration of the original liquor corresponds to the amounts of dye or colorless organic compound used.
  • the concentration in the squeezed or original liquor is measured by methods known per se, such as spectrophotometric e.g. at the absorption maximum or by chromatographic means (e.g. HPLC).
  • Mercerized cotton is used both for the determination of the affinity factor A from 1.1 to 4 and for the determination of the affinity factor B of at least 1.1, the concentration of water-soluble, fiber-affine, colorless organic compound being 0.2 to 0.3 g / I and 0.1 g / I of direct or reactive dye in the original liquor.
  • the water-soluble, fiber-affine, colorless organic compound alone or the direct or reactive dye alone is used.
  • the mercerized cotton [140 g / m 2 , thread count / cm 2 : warp / weft 25/22, yarn number: Tex warp / weft 30/30] 25 ° C and 60% relative humidity is conditioned to constant weight, the fabric is impregnated with a liquid absorption of approx. 200 percent by weight at room temperature with the original liquor containing a salt, in particular Na 2 S0 4, for example 10 g / l Na 2 S0 4 is squeezed to 70% weight gain after a diving time of approx. 2-4 seconds (including air passage) and the concentration of the squeezed liquor of dye or colorless compound is determined.
  • a salt in particular Na 2 S0 4
  • 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 0.05 g / l or less to about 20 g / i.
  • a particularly preferred embodiment of the process according to the invention is characterized in that a mixture of (1) at least one direct or reactive dye or at least one direct and at least one reactive dye and (2) at least one water-soluble anionic, fiber-affine, colorless organic compound is used, so that the dye affinity factor (B) in the mixture is 0.9 to 1.15, in particular 0.95 to 1.1.
  • the designation g / I means grams per liter.
  • the amount of water-soluble, fiber-affine, colorless organic compound in the process according to the invention depends in particular on the amount of dye used and the factor B, a minimum amount of 0.5 g / l having proven to be advantageous.
  • C 1 -C 4 alkyl means alkyl radicals or alkyl constituents which contain 1 to 4 carbon atoms and can be straight-chain or branched. Examples are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. Butyl, isobutyl and tert. Butyl.
  • Halogen means for example fluorine, bromine or preferably chlorine.
  • Acyl is especially formyl, C 1 -C 4 alkylcarbonyl, such as acetyl or propionyl, or benzoyl.
  • Suitable water-solubilizing group Z are, in particular, carboxyl groups or especially sulfonic acid groups.
  • a compound can contain both only carboxy groups or only sulfo groups as well as both carboxy and sulfo groups.
  • m is preferably 1 to 4.
  • Compounds of the formulas (1) to (3) preferably contain 2 to 4 acidic water-solubilizing groups Z, while the other compounds of the formula (4) contain in particular 1 or 2 water-solubilizing groups Z.
  • the phen group and the rings a and ⁇ can be hydroxyl, cyano, nitro, halogen, such as fluorine, chlorine or bromine, C 1 -C 4 alkyl, such as methyl, ethyl, propyl, isopropyl or butyl, trifluoromethyl, C 1 -C 4 alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy or butoxy, C 2 -C 5 alkoxycarbonyl, amino, mono- or di-C 1 -C 4 alkylamino, phenylamino, carbamoyl, sulfamoyl, ureido, C 1 -C 7 -Acylamino, such as acetylamino, propionylamino or benzoylamino, Ci-C 4 alkylsulfonyl, such as methylsulfonyl, sulfomethyl or sulfatoe
  • V is preferably R 2 -X 2 - and W is especially R 3 -X 3 -.
  • Compounds of the formula (1) in which Xi, X 2 and X 3 are -NH- or V and W, independently of one another, are preferably -OH or -NH 2 are particularly preferred.
  • Xi, X 2 and Xs each represent -NH-, R i , R 2 and Rs, independently of one another, phenyl or naphthyl, Z is the sulfonic acid group and m 2 or preferably 3 .
  • the compounds used in the process according to the invention are either in the form of the free acid or preferably as their salts.
  • suitable salts are the alkali metal, alkaline earth metal or ammonium salts or the salts of an organic amine.
  • suitable salts include the sodium, potassium or ammonium salts or the salt of triethanolamine.
  • the water-soluble, fiber-affine, colorless organic compounds used in the process according to the invention are known per se and can be prepared by methods known per se.
  • the reactive dyes of the formula (25) can contain up to six identical or different types of reactive radicals.
  • Fiber-reactive radicals X are to be understood as those which react with the hydroxyl groups of cellulose, the amino, carboxy, hydroxyl and thiol groups in wool and silk, or with the amino and possibly carboxy groups of synthetic polyamides to form covalent chemical bonds capital.
  • X is preferably a fiber-reactive radical of the aliphatic, aromatic or heterocyclic series which is bonded to the radical D directly or via a bridge member.
  • X is preferably directly or via an optionally monoalkylated amino group, such as -NH-, -N (CHa) -, -N (C 2 Hs) - or -N (C 3 H 7 ) - or via a bridge member containing an amino group, for example, phenylene bonded to the radical D.
  • an optionally monoalkylated amino group such as -NH-, -N (CHa) -, -N (C 2 Hs) - or -N (C 3 H 7 ) - or via a bridge member containing an amino group, for example, phenylene bonded to the radical D.
  • fiber-reactive radicals X of the heterocyclic series such as, for example, 2,4-dichlorotriazinyl-6, mono-, di- or trihalopyrimidinyl radicals, such as 2,4-dichloropyrimidinyl-6-, 2,4,5-trich - lorpyrimidinyl-6-, 2,4-Dichtor-5-nitro- or 5-methyl- or -5-carboxymethyl- or -5-carboxy- or -5-cyano- or -5-vinyl- or -5-sulfo - or -5-mono-, -di or -trichloromethyl- or 5-methylsulfonylpyrimidinyl-6-, 2,5-dichloro-4-methylsulfonyl-pyrimidinyl-6-, 2-fluoro-4-pyrimidinyl-, 2,6 -Difluoro-4-pyrimidinyl-, 2,6-difluoro-5-chloro
  • Particularly interesting fiber-reactive residues are fluorine or chloro-1,3,5-triazine residues of the formula where the substituents Qi on the triazine ring are in particular: -NH 2 , alkylamino, N, N-dialkylamino, cycloalkylamino, N, N-dicycloalkylamino, aralkylamino, arylamino groups, mixed substituted amino groups, such as N-alkyl-N- cyclohexylamino and N-alkyl-N-arylamino groups, furthermore amino groups which contain heterocyclic radicals which may have further fused-on carbocyclic rings, and amino groups in which the amino nitrogen atom is a member of an N-heterocyclic ring which optionally contains further heteroatoms, and hydrazino and Semicarbazido.
  • alkyl radicals can be straight-chain or branched, low molecular weight or higher molecular weight; alkyl radicals having 1 to 6 carbon atoms are preferred; suitable cycloalkyl, aralkyl and aryl radicals are, in particular, cyclohexyl, benzyl, phenethyl, phenyl and naphthyl radicals; heterocyclic radicals are especially furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzothiazole and benzoxazole; and as amino groups in which the amino nitrogen atom is a member of an N-heterocyclic ring, preference is given to residues of six-membered N-heterocyclic compounds which, as further heteroatoms, are nitrogen, May contain oxygen or sulfur.
  • alkyl, cycloalkyl, aralkyl and aryl radicals, the heterocyclic radicals and the N-heterocyclic rings can be further substituted, for example by: halogen, such as fluorine, chlorine and bromine, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C. 1-4 alkyl, C 1-4 alkoxy, acylamino groups such as acetylamino or benzoylamino, ureido, hydroxyl, carboxyl, sulfomethyl or sulfo.
  • halogen such as fluorine, chlorine and bromine, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C. 1-4 alkyl, C 1-4 alkoxy
  • acylamino groups such as acetylamino or benzoylamino, ureido, hydroxyl, carboxyl,
  • amino groups are: -NH 2 , methylamino, ethylamino, propylamino, isopropylamino, butylamino, hexylamino, ß-methoxyethylamino, ⁇ methoxypropylamino, ß-ethoxyethylamino, N, N-dimethylamino, N, N-diethylamino, ß ⁇ -cyanoethylamino, y-cyanopropylamino, ⁇ -carboxyethylamino, sulfomethylamino, ⁇ -sulfoethylamino, ß-hydroxyethylamino, N, N-di-ß-hydroxyethylamino, y-hydroxypropylamino, benzylamino, phenethylamino, cyclohexinoamino, phenylaminoilino, phenyla
  • the cation Ka in formula (26) means e.g. a hydrogen, sodium, potassium, lithium or ammonium ion or the cation of an organic amine, e.g. of triethanolamine.
  • Suitable water-soluble reactive dyes of the formula (26) are the dye residues D given under formula (25) which contain one to six, in particular up to two, reactive residues X.
  • the reactive dyes of the formula (25) or (26) can contain up to six identical or different reactive groups.
  • the reactive dyes of the formula (25) or (26) preferably contain highly reactive radicals X. These are radicals X which are more reactive than the 2-chloro-1,3,5-triazinyl radicals which are in the 4-position by one of the above mentioned substituents Q 1 are substituted.
  • Examples of such highly reactive radicals X are, for example: 2-fluoro-4- (Q 1 ) -triazinyl-6-, where the substituents given above for Qi are suitable, 2,4-dichlorotriazinyl-6-, 2,4 -Dichloropyrimidine-5-carbonyl-, 5-cyano- or 5-methylsulfonyl-2,4-dichloropyrimidinyl-6, difluorochloropyrimidinyl-, such as 2,4-difluoro-5-chloropyrimidinyl-6-, 2,3-dichloroquinoxaline-6 -carbonyl-, vinylsulfonyl-, ß-sulfatoethylsulfonyl-, ß-chloroethylsulfonyl-, ⁇ -thiosulfatoethylsulfonyl-, ⁇ -acetoxyethylsulfonyl-.
  • Reactive dyes of the formula (26) in which X is a radical of the formula are particularly preferably used in the process according to the invention , wherein R is hydrogen or C 1-4 alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl or tert-butyl, and Q 2 is an optionally substituted amino, a phenylenediamine bound difluorochloropyrimidinyl radical or a vinylsulfonyl-, ⁇ -sulfatoethylsulfonyl, ⁇ -thiosulfatoethylsulfonyl, ⁇ -chloroethylsulfonyl or ⁇ -acetoxyethylsulfonyl radical bound directly or via an aromatic or aliphatic bridge member.
  • R is hydrogen or C 1-4 alkyl, such as methyl, ethyl, propyl, isoprop
  • the dye liquor may also contain alkaline compounds for fixing the reactive dyes, for example sodium carbonate, sodium bicarbonate, sodium hydroxide, disodium phosphate, trisodium phosphate, borax, aqueous ammonia or alkali donors, such as e.g. Sodium trichloroacetate.
  • alkali donors such as e.g. Sodium trichloroacetate.
  • a mixture of water glass and a 30% aqueous sodium hydroxide solution has proven itself very well as an alkali.
  • the pH of the dye liquors containing alkali is generally 7.5 to 13.2, preferably 8.5 to 11.5.
  • the padding liquors are expediently prepared by dissolving the dye and by adding the water-soluble, fiber-affine, colorless organic compound and alkali.
  • the dyeing liquors can contain other conventional additives, e.g. Electrolytes, e.g. Sodium chloride or sodium sulfate as well as urea, glycerin and / or sodium formate.
  • thickeners such as e.g. Alginates, starch ether or locust bean gum may be contained therein.
  • 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 padding liquor are more appropriately between 1 to 10 g, preferably 0.5 to 3 g, per liter of liquor.
  • Dye fixation on pure cellulose fibers is carried out by customary methods, the fixing time and fixing temperature depending on the fiber material and, in the case of reactive dyes, on the reactivity of the reactive dyes used. Steaming times in saturated steam between 30 seconds and 15 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 8 minutes. In particular, the reactive dyes are fixed with steam at a temperature of 100 ° C to 150 ° C for 30 seconds to 12 minutes.
  • the dyes containing at least one reactive dye are fixed at 100 to 200 ° C., the fixing time being in particular between 10 seconds and 10 minutes at preferably 150 ° C. to 200 ° C. If necessary, the textile material is dried before fixing.
  • fixation can also be carried out using the cold dwell process; such as. 6 to 12 hours residence time at room temperature.
  • the dyed cellulose material can be washed out in the usual way 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.
  • Suitable cellulose fibers are natural fibers, such as mercerized or bleached cotton and linen (bleached), and regenerated fibers, such as viscose, polynosic and copper rayon. Mainly woven or knitted fabrics of these fibers are used.
  • the dive time is 2 seconds.
  • the affinity factor B 1 of the dye specified above in the padding liquor above is 1.05.
  • the affinity factor is determined spectrophotometrically (UVICON 810), the concentration of the padding liquor prior to impregnation and the concentration of the squeezed liquor being determined.
  • the affinity factor is defined as:
  • the affinity factor is a critical variable for the end inequality based on differences in affinity of the dyes. With a value approximating the ideal affinity factor of 1.0 of approx. 0.95 to 1.05, no end inequality is discernible.
  • the quantity stated for the water-soluble, fiber-affine, colorless organic compound and the numerical values for the affinity factor A relate to commercially available pure substances with an active substance content of at least 70%.
  • the cotton cretonne fabric is dried at 100 ° for one minute, padded with a liquor containing 250 g / l NaCl and 10 ml / l 30% NaOH with a squeezing effect of about 80% and then for one minute fixed in saturated steam at 101 to 103 ° .
  • the cotton cretonne fabric is then rinsed first with cold water and then with hot to boiling water, soaped at the boil with 1 to 2 g / l of a detergent, rinsed again with hot and then with cold water and then dried.
  • Comparative Example 1 If the procedure described in Example 1 is followed, but a padding liquor is used without the compound of the formula (201), then a cotton cretonne fabric dyed differently in orange color is obtained, the beginning of the lot towards the end of the lot is colored darker because the squeezed liquor is depleted of dye and thus diluted.
  • the affinity factor of the orange-colored dye from Example 1 in the padding liquor without the compound of the formula (201) is 1.23.
  • the dive time is 2 seconds.
  • the affinity factor of the above-mentioned dye in the above padding liquor, determined according to the information in Example 1 at ⁇ max 550 nm, is 1.04.
  • the padded fabric is then dried on the hot flue at 100 ° for 1 minute and then heat set on the hot flue at 160 ° for 1 minute.
  • Comparative Example 2 If the procedure described in Example 2 is followed, but a padding liquor is used without the compound of the formula (202), a cotton cretonne fabric dyed in different shades of red is obtained, the beginning of the lot compared to the end of the lot is colored much darker.
  • the affinity factor of the red-coloring dye from Example 2 in the padding liquor without the compound of the formula (202) is 1.21; determined according to the information in Example 1.
  • the cellulose is steamed with saturated steam at 101 to 103 ° for one minute.
  • a cellulosic cretonne fabric dyed in beige color with good fastness properties is obtained.
  • the dive time is 2 seconds.
  • the affinity factor of the above-mentioned dye in the above liquor, determined according to the information in Example 1 at ⁇ max 625 nm, is 1.02.
  • the cotton fabric is dried on the hot flue for one minute, padded with a liquor containing 250 g / l NaCl and 10 ml / l 30% NaOH with a squeezing effect of approx. 80% and then with saturated steam at 101 to 103 ° steamed for one minute.
  • a cotton fabric dyed in the same shade of blue with good fastness properties is obtained.
  • Comparative Example 4/1 If the procedure is as described in Example 4, but a padding liquor is used without the compound of the formula (204), a cotton fabric dyed in a different shade of blue is obtained. The affinity factor of the dye used in the padding liquor without the compound of the formula (204) is 1.40.
  • the affinity factor of H-acid in a pad liquor containing 10 g / l Na2S04 with 0.3 g / i H-acid is 1.00.
  • a colorless, water-soluble, organic compound with an affinity factor of 1.0 used in the padding liquor has no influence on the affinity factor of the dye used and thus the end imbalance is not improved.
  • the dive time is 2 seconds.
  • the goods speed is 10 m / minute.
  • the fabric is then fixed in a continuous steamer with saturated steam from 101 ° to 103 ° for 2 minutes.
  • the fabric is then rinsed and dried several times.
  • Comparative Example 5 If the procedure is as described in Example 5, but a padding liquor is used without the compound of the formula (205), a piece of fabric colored differently in the end is obtained.
  • the affinity factor of the dye without the compound of formula (205) in the padding liquor is 1.11.
  • the dive time is 2 seconds.
  • polyester / cotton blend is then dried at 100 ° for 1 minute and then thermosolated at 210 °.
  • Example 2 After the washing, soaping and rinsing and drying given in Example 2, a piece of fabric of the same color, dyed in yellow, is obtained.
  • Comparative Example 6 If the procedure is as described in Example 6, but a padding liquor is used without the compound of the formula (206), a polyester / cotton blend fabric dyed yellow is obtained. The affinity factor of the dye without the compound of formula (206) in the padding liquor is 1.24.
  • the cotton jersey is then left to stand for 6 hours at room temperature with no air.

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Claims (35)

1. Procédé pour la teinture à égalité de nuance d'un bout à l'autre de fibres cellulosiques ou de fibres mélangées contenant de la cellulose avec des colorants directs et/ou réactifs selon le procédé par fou- lardage, caractérisé par le fait que l'on utilise un bain aqueux contenant au moins un colorant direct et/ou réactif et au moins un composé organique incolore, soluble dans l'eau, anionique, présentant une affinité pour les fibres, ayant un facteur d'affinité A pour le coton mercerisé, pour une concentration de 0,2-0,3 gramme par litre, de 1,1 à 4, le facteur A étant le quotient de la concentration du composé organique incolore, soluble dans l'eau, présentant une affinité pour les fibres, dans un bain sans colorant avant l'imprégnation sur la concentration du composé dans le bain sans colorant après l'exprimage.
2. Procédé selon la revendication 1, caractérisé par le fait que l'on utilise de colorants directs ou réactifs qui ont un facteur d'affinité B pour le coton mercerisé, pour une concentration de 0,1 gramme par litre, d'au moins 1,1, le facteur B étant le quotient de la concentration du colorant dans le bain d'origine sans addition du composé organique incolore sur la concentration du colorant dans le bain après expri- mage.
3. Procédé selon la revendication 1, caractérisé par le fait que l'on utilise un bain aqueux dans lequel la concentration globale du colorant et du composé organique incolore, soluble dans l'eau, présentant une affinité pour les fibres, est d'au maximum 20 grammes par litre.
4. Procédé selon la revendication 3, caractérisé par le fait que la concentration globale du colorant et du composé incolore s'élève au maximum à 10 grammes par litre.
5. Procédé selon la revendication 4, caractérisé par le fait que la concentration globale du colorant et du composé incolore s'élève à 3 à 8 grammes par litre.
6. Procédé selon la revendication 1, caractérisé par le fait que la concentration du colorant est inférieure à 5 grammes par litre, en particulier est inférieure à 3 grammes par litre.
7. Procédé selon la revendication 1, caractérisé par le fait que l'on utilise un composé organique incolore, soluble dans l'eau, anionique, présentant une affinité pour les fibres, ayant un facteur d'affinité A compris entre 1,15 et 2,5, en particulier compris entre 1,2 et 1,6.
8. Procédé selon la revendication 1, caractérisé par le fait que l'on utilise un mélange comprenant (1) au moins un colorant direct ou réactif ou leur mélange en même temps que (2) au moins un composé organique incolore, soluble dans l'eau, anionique, présentant une affinité pour les fibres, le facteur d'affinité B pour le colorant dans le mélange étant compris entre 0,9 et 1,15, en particulier entre 0,95 et 1,1.
9. Procédé selon la revendication 1, caractérisé par le fait que l'on utilise comme composé organique incolore
(a) un composé de formule
Figure imgb0114
où
Q représente
Figure imgb0115
ou
Rx représente un hydrogène, un halogène, un cyano, un reste alkyle en Ci-C4 ou un reste alkylsulfo- nyle en C1-C4,
V et W représentent, indépendamment l'un de l'autre, R2-X2, R3-X3, un hydroxy, un reste alcoxy en C1-C4 ou un groupe amino non substitué ou bien mono- ou disubstitué par un reste alkyle en C1-C4, le reste alkyle étant non substitué ou à substituant(s) hydroxy, cyano, sulfo ou sulfato,
Ri, R2, R3 représentent, indépendamment les uns des autres, un reste aromatique ou hétéroaroma- tique,
Xi, X2 et X3 représentent, indépendamment les uns des autres,
-O-, -S-,
Figure imgb0116
ou -NH-CO-Phen-NH-,
R4 représente un hydrogène, un reste alkyle alkyle en Ci-C4 ou un reste phényle, Phen représente un groupe phénylène non substitué ou substitué,
Z représente un groupe acide, solubilisateur dans l'eau, et
m représente 1 à 6, ou bien
b) un composé de formule
Figure imgb0117
où Ri, R2, Z et m ont la signification indiquée,
A représent la liaison directe, -CO-, -CONH- ou
Figure imgb0118
et les cycles a et p sont substitués ou bien
c) un composé de formule
Figure imgb0119
ou
Rs et R6 représentent, indépendamment l'un de l'autre, -NH2, -NH-CO-R7, -N02 ou
Figure imgb0120
R7 représente un reste alkyle en Ci-Ce ou un reste aryle et V, W, Z et m ont la signification indiquée ci-dessus, ou bien
d) un composé de formule
Figure imgb0121
ou
R8 représente un hydrogène ou R9-CO- et
R9 représente un aliphatique, aromatique ou hétérocyclique, les cycles a et β sont substitués ou non substitués et Z et m ont la signification indiquée ci-dessus.
10. Procédé selon la revendication 9, caractérisé par le fait que l'on utilise un composé de formule (1) où Q représente -N=.
11. Procédé selon une des revendications 9 et 10, caractérisé par le fait que l'on utilise un composé de formule (1) où V représente R2-X2- et W représente R3-X3-.
12. Procédé selon une des revendications 9 à 11, caractérisé par le fait que, dans la formule (1), X1, X2 et X3 représentent chacun -NH-.
13. Procédé selon une des revendications 9 à 12, caractérisé par le fait que, dans la formule (1), Ri, R2 et Rs représentent chacun un reste aryle.
14. Procédé selon une des revendications 9 à 10, caractérisé par le fait que, dans la formule (I), V représente un hydroxyle et W représente R3-X3-.
15. Procédé selon la revendication 9, caractérisé par le fait que, dans la formule (3), R5 et R6 représentent chacun le reste triazinyle:
Figure imgb0122
16. Procédé selon une des revendications 9 à 15, caractérisé par le fait que, dans les formules correspondantes, m est 1 à 4.
17. Procédé selon une des revendications 9 à 16, caractérisé par le fait que Z représente le groupe sulfonique.
18. Procédé selon la revendication 9, caractérisé par le fait que l'on utilise comme composé organique incolore un composé de formule
Figure imgb0123
Rx représente un hydrogène, un halogène, un cyano, un reste alkyle en C1-C4 ou un reste alkylsulfony- le en C1-C4, Ri, R2 et R3 représentent, indépendamment les uns des autres un reste phényle, biphénylyle, naphtyle, stilbényle ou quinolinyle, qui est non substitué ou à substituant(s) alkyle en C1-C4, halogène, trifluorométhyle, nitro, cyano, hydroxy, alcoxy en C1-C4, amino, monoalkylamino en C1-C4, dialkyl-C1-C4-amino, phénylamino, acylamino en C1-C7, carbamoyle, uréido, sulfamoyle, alcoxy-C2-C5-carbonyle, alkyl-C1-C4-sulfonyle ou sulfométhyle,
Xi, X2 et X3 représentent, indépendamment les uns des autres, -O-, -S-,
Figure imgb0124
ou
Figure imgb0125
où R4 représente un hydrogène, un reste alkyle en C1-C4, ou le reste phényle et le cycle benzènique a n'est pas substitué ou est substitué par un des substituants indiqués pour Ri, Z représente un groupe carboxyle ou sulfonique et m représente 2 à 6.
19. Procédé selon la revendication 9, caractérisé par le fait que l'on utilise comme composé organique incolore un composé de formule
Figure imgb0126
où Rx représente un hydrogène, un halogène, un cyano, un reste alkyle en C1-C4 ou un reste alkyl-C1-C4-sulfonyle,
V' et W' représentent, indépendamment l'un de l'autre, un hydroxy, un reste alcoxy en Ci-C4 ou un groupe amino non substitué ou mono- ou disubstitué par un reste alkyle en C1-C4, le reste alkyle étant non substitué ou à substitué ou à substituant(s) hydroxy, cyano, sulfo ou sulfato, et V' représente aussi le reste R2-X2-,
R1 et R2 représentent, indépendamment l'un de l'autre, un reste phényle, biphénylyle, naphtyle, stilbényle ou quinolinyle, qui n'est pas substitué ou qui est à substituant(s) alkyle en Ci-C4, halogène, trifluorométhyle, nitro, cyano, hydroxy, alcoxy en C1-C4, amino, monoalkylamino en C1-C4, dialkyl-C1-C4-amino, phénylamino, acylamino en Ci-C7, carbamoyle, uréido, sulfamoyle, alcoxy-C2-C5-carbonyle, alkyl-C1-C4-sulfonyle ou sulfométhyle,
X1 et X2 représentent, indépendamment l'un de l'autre, -O-, -S-,
Figure imgb0127
ou
Figure imgb0128
où R4 est un hydrogène, un reste alkyle en C1-C4 ou le reste phényle et le cycle benzénique a n'est pas substitué ou est substitué par un des substituants indiqués pour Ri,
Z représente un groupe carboxyle ou sulfonique et m représente 2 à 4.
20. Procédé selon la revendication 9, caractérisé par le fait que l'on utilise comme composé organique incolore un composé de formule
Figure imgb0129
où R1, R2 et R3 représentent, indépendamment les uns des autres, un reste phényle, biphenylyle, naphtyle, stilbényle ou quinolinyle, qui n'est pas substitué ou est à substituant(s) alkyle en C1-C4, halogène, trifluorométhyle, nitro, cyano, hydroxy, alcoxy en C1-C4, amino, monoalkylamino en C1-C4, dialkyl-C1-C4- amino, phénylamino, acyl-C1-C7-amino, carbamoyle, uréido, sulfamoyle, alcoxy-C2-C5-carbonyle, alkyl-C1-C4-sulfonyle ou sulfométhyle,
X1, X2 et X3 représentent, indépendamment les uns des autres, -0-, -S-,
Figure imgb0130
ou
Figure imgb0131
ou R4 représente un hydrogène, un reste alkyle en C1-C4 ou le reste phényle et le cycle benzènique a n'est pas substitué ou est substitué par un des substituants indiqués pour R1, Z représente un groupe carboxyle ou sulfonique et m représente 2 à 6.
21. Procédé selon la revendication 20, caractérisé par le fait que l'on utilise un composé triazinique de formule (7), ou X1, X2 et Xs représentent chacun -NH-, Ri, R2 et Rs représentent, indépendamment les uns des autres, le reste phényle ou le reste naphtyle, Z représente le groupe sulfonique et m signifie 2 ou 3.
22. Procédé selon la revendication 9, caractérisé par le fait que l'on utilisé comme composé organique incolore un composé de formule
Figure imgb0132
où V' et W' représentent, indépendamment l'un de l'autre, un hydroxy, un reste alcoxy en C1-C4 ou un groupe amino non substitué ou mono- ou disubstitué par un reste alkyle en C1-C4, le reste alkyle n'étant pas substitué ou étant à substituant(s) hydroxy, cyano, sulfo ou sulfato et V' représente aussi le reste R2-X2-,
Ri et R2 représentent, indépendamment l'un de l'autre, un reste phényle, biphénylyle, naphtyle, stilbényle ou quinolinyle, qui n'est pas substitué ou qui est à substituant(s) alkyle en C1-C4, halogène, trifluorométhyle, nitro, cyano, hydroxy, alcoxy en C1-C4, amino, monoalkylamino en C1-C4, dialkyl-C1-C4-amino, phénylamino, acyl-Ci-C7-amino, carbamoyle, uréido, sulfamoyle, alcoxy-C2-C5-carbonyle, alkyl-C1-C4-sulfonyle ou sulfométhyle,
X1 et X2 représentent, indépendamment l'un de l'autre, -0-, -S-,
Figure imgb0133
ou
Figure imgb0134
où R4 représente un hydrogène, un reste alkyle en C1-C4 ou le reste phényle et le cycle benzénique a n'est pas substitué ou est substitué par un des substituants indiqués pour Ri, Z représente un groupe carboxyle ou sulfonique et m représente 2 à 4.
23. Procédé selon la revendication 9, caractérisé par le fait que l'on utilise comme composé organique incolore un composé de formule
Figure imgb0135
où R1 et R2 représentent, indépendamment l'un de l'autre, un reste phényle, biphenylyle, naphtyle, stilbényle ou quinolinyle, qui n'est pas substitué ou qui est à substituant(s) alkyle en Ci-C4, halogène, trifluorométhyle, nitro, cyano, hydroxy, alkoxy en Ci-C4, amino, monoalkylamino en C1-C4, dialkyl-C1-C4-amino, phénylamino, acyl-C1-C7-amino, carbamoyle, uréido, sulfamoyle, alcoxy-C2-C5-carbonyle, alkyl-C1-C4-sulfonyle ou sulfométhyle,
Z représente un groupe carboxyle ou sulfonique et m représente 2 à 4.
24. Procédé selon la revendication 9, caractérisé par le fait que l'on utilise comme composé organique incolore un composé de formule
Figure imgb0136
où R1 et R2 représentent, indépendamment l'un de l'autre, un reste phényle, biphénylyle, naphtyle, stilbényle ou quinolinyle, qui n'est pas substitué ou qui est à substituant(s) alkyle en C1-C4, halogène, trifluorométhyle, nitro, cyano, hydroxy, alcoxy en Cl-C4, amino, monoalkylamino en C1-C4, dialkyl-Ci-C4-amino, phénylamino, acyl-C1-C7-amino, carbamoyle, uréido, sulfamoyle, alcoxy-C2-C5-carbonyle, alkyl-C1-C4-sulfonyle ou sulfométhyle, Z représente un groupe carboxyle ou sulfonique et m représente 2 à 4.
25. Procédé selon la revendication 9, caractérisé par le fait que l'on utilise comme composé organique incolore un composé de formule
Figure imgb0137
où R1 et R2 représentent, indépendamment l'un de l'autre un reste phényle, biphénylyle, naphtyle, stilbényle ou quinolinyle, qui n'est pas substitué ou qui est à substituant(s) alkyle en C1-C4, halogène, trifluorométhyle, nitro, cyano, hydroxy, alcoxy en Ci-C4, amino, monoalkylamino en CI-C4, dialkyl-C1-C4-amino, phénylamino, acyl-Ci-C7-amino, carbamoyle, uréido, sulfamoyle, alcoxy-C2-C5-carbonyle, alkyl-C1-C4-sulfonyle ou sulfométhyle, Z représente un groupe carboxyle ou sulfonique et m représente 2 à 4.
26. Procédé selon la revendication 9, caractérisé par le fait que l'on utilise comme composé organique incolore un composé de formule
Figure imgb0138
où Ri et R2 représentent, indépendamment l'un de l'autre, reste phényle, biphénylyle, naphtyle, stilbényle ou quinolinyle, qui n'est pas substitué ou qui est à substituant(s) alkyle en C1-C4, halogène, trifluorométhyle, nitro, cyano, hydroxy, alcoxy en C1-C4, amino, monoalkylamino en Ci-C4, dialkyl-C1-C4-amino, phénylamino, acyl-C1-C7-amino, carbamoyle, uréido, sulfamoyle, alcoxy-C2-C5-carbonyle, alkyle-Ci-C4-sulfonyle ou sulfométhyle, Z représente un groupe carboxyle ou sulfonique et m représente 2 à 4, et les cycles benzèniques α et p ne sont pas substitués ou sont substitués par un des substituants indiqués pour Ri.
27. Procédé selon la revendication 1, caractérisé par le fait que l'on utilise au moins un colorant réactif soluble dans l'eau de formule
Figure imgb0139
où D est le reste d'un colorant organique de la série monozoïtique, polyazoïque, azoïque à complexe métallique, anthraquinone, phthalocyanine formazan, azométhine, nitroaryle, dioxazine, phénazine ou stilbène, X est un reste réactif sur les fibres de la série aliphatique, aromatique ou hétérocyclique, qui est lié au reste D directement ou par un chaînon pontant, et q = 1, 2, 3, 4, 5 ou 6.
28. Procédé selon la revendication 27, caractérisé par le fait que l'on utilise au moins 2 ou 3 colorants réactifs de formule (25).
29. Procédé selon la revendication 28, caractérisé par le fait que l'on utilise pour la teinture en trichromie au moins un colorant en jaune ou en orange, au moins un colorant réactif colorant en rouge et au moins un colorant réactif colorant en bleu.
30. Procédé selon la revendication 27, caractérisé par le fait que l'on utilise au moins un colorant réactif soluble dans l'eau de formule
Figure imgb0140
où D représente le reste d'un colorant monoazoïque, disazoïque, azoïque à complexe métallique, anthra- quinonique, formazan ou dioxazine, Ka représente un cation et n = 1, 2, 3, 4, 5 ou 6, et X et q ont les significations indiquées dans la revendication 27 sous la formule (25).
31. Procédé selon la revendication 30, caractérisé par le fait que l'on utilise au moins un colorant réactif soluble dans l'eau de formule (26), où X est un reste de formule
Figure imgb0141
où R représente un hydrogène ou un reste alkyle en C1-C4, Q2 représente un groupe amino éventuellement substitué, un reste difluorochloropyrimidinyle lié par un reste phénylènediamine ou un reste vinyl- sulfonyle, β-sulfatoéthylsulfonyle, β-thiosulfatoéthylsulfonyle, β-chloréthylsulfonyle ou β-acétoxy- éthylsulfonyle, lie par un chaînon pontant aromatique ou aliphatique, et Y' représente un fluor ou un chlore.
32. Procédé selon la revendication 1, caractérisé par le fait que l'on teint des fibres cellulosiques pures.
33. Procédé selon la revendication 1, caractérisé par le fait que l'on teint des fibres mélangées polyester/cellulose.
34. Procédé selon la revendication 1, caractérisé par le fait que l'on teint en continu.
35. Procédé selon la revendication 1, caractérisé par le fait que l'on teint les fibres cellulosiques avec des colorants réactifs et que l'on fixe ceux-ci à la vapeur à une température comprise entre 100°C und 150°C pendant 30 secondes à 12 minutes.
EP87810172A 1986-04-07 1987-03-24 Procédé de teinture de fibres cellulosiques ayant une égalité de nuance entre les extrémités du tissu Expired EP0242324B1 (fr)

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US4886518A (en) * 1987-10-01 1989-12-12 Ciba-Geigy Corporation Dyeing cellulose fibres without incurring ending with colorless pyrimidine, triazine, aromatic, furfuryl or quinolinyl compound
EP0356394A3 (fr) * 1988-08-26 1990-03-21 Ciba-Geigy Ag Colorants réactifs, leur préparation et leur utilisation
EP0373117A1 (fr) * 1988-12-06 1990-06-13 Ciba-Geigy Ag Procédé de teinture de matières fibreuses contenant de la cellulose avec des colorants réactifs
FR2768645A1 (fr) * 1997-09-22 1999-03-26 Valbopan Fibras De Madeira Sa Composition et procede de fabrication de materiaux composites a base de fibres de bois et materiaux obtenus
US6184226B1 (en) 1998-08-28 2001-02-06 Scios Inc. Quinazoline derivatives as inhibitors of P-38 α
CN103556339A (zh) * 2013-11-11 2014-02-05 江苏通海线业有限公司 一种丝光棉、茶纤维和桑皮纤维的混纺纱
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US2928711A (en) * 1960-03-15 New colouration process
GB482345A (en) * 1936-09-25 1938-03-25 Of Chemical Industry Soc Improvements in or relating to the production of dyed or printed materials
DE1059399B (de) * 1956-11-21 1959-06-18 Ici Ltd Verfahren zum Faerben und Bedrucken von cellulosehaltigen Textilien
GB884158A (en) * 1959-08-28 1961-12-06 Ici Ltd New colouration process for cellulose textile materials
DE1147191B (de) * 1961-02-23 1963-04-18 Basf Ag Verfahren zum Faerben, Bedrucken und bzw. oder optischen Aufhellen von Textilgut
US3400121A (en) * 1966-03-30 1968-09-03 Hoechst Ag 2, 4, 6-tri-(1-amino-substituted aromatic)-s-triazines
CH532684A (de) * 1969-01-30 1972-09-29 Ciba Geigy Ag Verfahren zum Färben und Bedrucken von Zellulosefasern
GB1318879A (en) * 1969-09-15 1973-05-31 Ici Ltd Colouration process
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
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