EP1504149A2 - Procede pour azurer des materiaux textiles - Google Patents

Procede pour azurer des materiaux textiles

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Publication number
EP1504149A2
EP1504149A2 EP03717323A EP03717323A EP1504149A2 EP 1504149 A2 EP1504149 A2 EP 1504149A2 EP 03717323 A EP03717323 A EP 03717323A EP 03717323 A EP03717323 A EP 03717323A EP 1504149 A2 EP1504149 A2 EP 1504149A2
Authority
EP
European Patent Office
Prior art keywords
compound
weight
dyes
compounds
general formula
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.)
Granted
Application number
EP03717323A
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German (de)
English (en)
Other versions
EP1504149B1 (fr
Inventor
Dieter Weber
Helmut Reichelt
Gerhard Wagenblast
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BASF SE
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BASF SE
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Publication of EP1504149B1 publication Critical patent/EP1504149B1/fr
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—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 azo dyes
    • D06P1/04—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 azo dyes not containing metal
    • D06P1/08—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 azo dyes not containing metal cationic azo dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60—Optical bleaching or brightening
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40—Dyes ; Pigments
    • C11D3/42—Brightening agents ; Blueing agents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60—Optical bleaching or brightening
    • D06L4/614—Optical bleaching or brightening in aqueous solvents
    • D06L4/636—Optical bleaching or brightening in aqueous solvents with disperse brighteners
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60—Optical bleaching or brightening
    • D06L4/657—Optical bleaching or brightening combined with other treatments, e.g. finishing, bleaching, softening, dyeing or pigment printing
    • 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
    • D06P1/13—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 azomethine 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
    • D06P1/16—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 dispersed, e.g. acetate, dyestuffs
    • D06P1/18—Azo 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
    • D06P1/16—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 dispersed, e.g. acetate, dyestuffs
    • D06P1/20—Anthraquinone dyes

Definitions

  • the present invention relates to a process for lightening textile materials by treatment with optical brighteners in an aqueous liquor, characterized in that 20 to 80% by weight, based in each case on the sum of all brightening compounds, of compound I
  • R is selected from C -C -oalkyl
  • the treatment optionally being carried out in the presence of one or more blue or violet shading dyes from the class of the anthraquinones, azo dyes or methine dyes.
  • radicals R 1 and R 2 can be, for example, hydrogen, fluorine, chlorine, phenyl, trifluoromethyl, alkyl or numerous other radicals and where V is selected from
  • Compounds of the general formula 1 can be applied at low temperature, but their abundance is limited, ie a lot of product is required to achieve the desired whitening effect. Also known is a process for lightening textiles by treating the textiles with distyrylbenzene compounds, for example from CH-A 366 512, CH-A 382 709, CH-A 388 294, CH-A 389 585, CH-A 411 329 , CH-A 416 078 and CH-A 465 548 are known.
  • EP-A 0 023 027 and EP-B2 0 030 917 and the literature cited in EP-B2 0 030 917 demonstrate the use of mixtures of two or more dicyanostyrylbenzene compounds for the optical brightening of polyesters.
  • EP 0 023 026 discloses mixtures of optical brighteners which contain 0.05 to 0.95 parts by weight of one or more compounds of the formula 2 p
  • A is a phenyl group substituted with an ortho- or para-cyano group, and 0.95 to 0.05
  • radicals R 1 and R 2 can mean: hydrogen, fluorine, chlorine, phenyl, trifluoromethyl, Ci-Cg-alkyl, alkoxy, alkylamino and numerous other radicals, which are listed on page 2, lines 14-21, and V as defined above,
  • R 4 from -CC alkoxy groups and R 5 is selected for example from Ci-Cg-alkyl and B is preferably a functional group, or further with compounds of the formulas 5b to 6b
  • radicals R 6 to R 10 are in each case selected from different groups and V is defined as above.
  • the brighteners defined in this way are applied using various methods and give a good degree of whiteness according to CIE.
  • EP-A 0 023 028 claims mixtures containing 0.05 to 0.95 parts by weight of a mixture consisting of 20 to 100% by weight of 2 p, o '
  • R 1 and R 2 independently of one another denote H or -CC 6 alkyl
  • A is selected from N and CH and X is selected from
  • the mixtures show a synergistic effect with regard to the CIE whiteness and good light fastness.
  • EP-A 0 321 393 describes the use of compounds of type 1 b
  • D is a C ⁇ -C alkyl group
  • compounds of formula 2 described in brightener dispersions.
  • the compounds of type 1 b or 2 are disclosed either individually or as special mixtures, referred to in the cited document as mixtures 1 to 6 (page 6-8). It is essential to the invention in EP-A 0 321 393 that the mixture contains a copolymer of 2-vinylpyrrolidone with 3-vinylpropionic acid (page 9, line 18).
  • EP-A 0 682 145 improves the light fastness of textiles by treating them with formulations which contain a fluorescent UV absorber which absorbs at a wavelength of 280 to 400 nm, selected from 4.4 ⁇ -bis- Triazinyl-aminostilbene-2, 2'-disulfonic acids, 4, 4 v -diphenylstilbenes, 4,4'-distyrylbiphenyls, 4-phenyl-4 v -benzoxazyl-stilbenes, stilbenylnaphthotriazoles, 4-styrylstilbenes, coumarins, pyrazolines, naphthalimides Triazinylpyrenes, 2-styrylbenzoxzaol or 2-styrylnaphthoxazole derivatives, benzimidazolbenzofurans, oxanilide derivatives and bis-benzoxazol-2-yl and bis-benzimidazol-2-yl derivatives applies
  • R 14 is independently hydrogen or -CC alkyl or tert. -Butyl or
  • R 15 and R 16 are the same or different and are selected from H, -CC 4 alkyl and CH 2 -CH 2 -OH,
  • R 17 radicals are the same or different and are selected from H and S0 3 _
  • X is selected from
  • a brilliant white is of great economic importance for a wide variety of products, such as textiles and plastic moldings.
  • the brighteners have a better spread, i.e. one achieves an effect of the same size or even greater with less brightener.
  • Textile materials within the meaning of the present invention include fibers, roving, yarn, twine, woven goods, knitted fabrics,
  • Nonwovens, garments understood from, for example, polyesters or polyester mixtures.
  • the textile materials preferably consist of synthetic polyester or of mixtures containing 45 to 90% by weight of polyester.
  • brightening or optically brightening compounds are understood to be fluorescent compounds which can absorb in the range from 280 to 400 nm and emit at a higher wavelength.
  • Examples of compounds from the class of the stilbenes, distyrylbenzenes, diphenyldistyryls, triazinyls, benzoxazoles, bisbenzoxazoles, bisbenzoxazolylthiophenes, bisbenzoxazolylnaphthalenes, pyrenes, coumarins and naphthalene peridicarboximides are mentioned.
  • brightening or optically brightening compounds are understood to be those of the formulas I, II and III. Data in% by weight relate to the following on the sum of the brightening compounds, unless expressly stated otherwise.
  • aqueous liquors are also understood to mean those liquors which, in addition to water as the main constituent, contain up to 40% by volume of one or more further solvents, for example alcohols such as ethanol.
  • the pH of the liquors used according to the invention is preferably from 3 to 12, preferably 3 to 8.
  • textile materials are treated with 20 to 80, preferably 20 to 70% by weight and particularly preferably 30 to 50% by weight of the compound of the formula I.
  • R is selected from C 4 -C ⁇ o-alkyl, for example n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, sec-pentyl, neo-pentyl, 1, 2 -Dimethylpropyl, iso-amyl, n-hexyl, iso-hexyl, sec.-hexyl, n-heptyl, iso-heptyl, n-octyl, 2-ethylhexyl, n-nonyl and n-decyl; n-butyl and 2-ethylhexyl are preferred.
  • I also means mixtures of isomers which contain 0.2 to 40 mol%, preferably 0.7 to 20 mol%, of cis isomer.
  • the proportion of cis isomer is determined by spectroscopic or chromatographic methods familiar to the person skilled in the art, see FIG. for example J. Chromat. 1967, 27 (2), 413-22.
  • the dicyanostyryl compounds II p, o ', II m, p', II p, p 'and II o, o' used are used in the form of their trans isomers.
  • Suitable shading dyes generally come from the class of disperse dyes and vat dyes. These are common names. The color index contains such dyes e.g. listed as Disperse Blue or Disperse Violet or Vat Blue or Vat Violet.
  • Blue dyes from the class of anthraquinones, azo dyes or methine dyes are particularly suitable.
  • Dyes from the class of anthraquinones obey, for example, the formulas A 1 to A 4
  • Ci-Cio-alkyl which is optionally interrupted 1 or 2 oxygen atoms in ether function and can be substituted by -C-C 4 alkoxycarbonyl or cyano or optionally substituted by -C-C 4 alkoxy, phenyl, substituted phenyl,
  • Ci-Cio-alkyl which is optionally interrupted by 1 or 2 oxygen atoms in ether function and can be substituted by hydroxy, phenyl or Ci-Cs-Al oxycarbonyl, Z 3 oxygen or NH,
  • Z 4 is hydrogen, Ci-Cio-alkyl which may be interrupted by 1 or 2 oxygen atoms in ether function and which may be substituted by C 1 -C 4 -alkoxycarbonyl or cyano, or unsubstituted or C ⁇ -C 4 alkoxy,
  • Z 5 is hydrogen or halogen or CN
  • Z 6 is hydrogen or nitro
  • Z 7 is C 2 -C 6 alkylene or phenylene.
  • Dyes of the formula A2 are e.g. in US-A 2,628,963, US-A 3,835,154, DE-A 12 66 425 or DE-A 20 16 794.
  • Dyes that obey the formula AI, A3 and A4 are e.g. from K. Venkataraman, "The Chemistry of Synthetic Dyes", Volume 3, pages 391 to 423, 1970.
  • Suitable azo dyes are in particular monoazo dyes with a diazo component from the aniline or heterocyclic series and a coupling component from the aniline or heterocyclic series.
  • Suitable heterocycles from which the diazo components are derived are e.g. from the class of aminothiophenes, aminothiazoles, aminoisothiazoles, aminothiadiazoles or aminobenzisothiazoles.
  • Suitable heterocycles from which the coupling components are derived are e.g. from the class of the thiazoles or diamino-pyridines.
  • Such azo dyes in particular correspond to one of the formulas B 1 to B 7
  • Z 9 is hydrogen, halogen, Ci-Cs-alkoxy, phenoxy, Ci-C ⁇ -alkylthio, phenylthio, C ⁇ -C 4 alkylsulfonyl, phenylsulfonyl, methyl or optionally substituted by chlorine, methoxy, ethoxy or methyl-substituted phenyl,
  • Ci-Cs-alkyl which can be interrupted by 1 to 3 oxygen atoms in ether function and by hydroxy, cyano, chlorine, phenyl, Ci-C ß -alkoxy, Ci-C ⁇ -alkoxycarbonyl, Ci -C ⁇ -alkoxycarbonyloxy or C ⁇ -Cs-mono- or dialkylaminocarbonyloxy may be substituted, or C 3 -C 4 -alkenyl or Z 11 , but not Z 12 also hydrogen,
  • Y 1 is hydrogen, C ⁇ -C 4 alkyl, C ⁇ C 4 alkoxy, chlorine, bromine or a radical of the formula -NH-CO-R 11 , where R 11 is C 1 -C 4 alkyl, which is by C ⁇ - C 4 alkoxy, Cyano, hydroxy, chlorine or -CC 4 -alkanoyloxy can be substituted, or C 2 -C -alkenyl is,
  • Y 2 is hydrogen, -CC 4 alkyl or -C ⁇ alkoxy
  • Z 13 optionally substituted by C 1 -C 4 -alkoxy-C 4 alkyl, optionally substituted by C 1 -C 4 -alkoxy benzyl, optionally substituted by chlorine, methyl, methoxy or ethoxy-phenyl, pyrid-2-yl or pyrid-3- yl,
  • Z 15 optionally substituted by -CC 4 alkoxy or acetylamino thienyl or pyridyl and
  • Z 16 is cyano, chlorine or bromine.
  • Dyes of the formula B1 and B2 are e.g. in US 5,283,326 or US 5,145,952.
  • Dyes of the formula B3 are known from EP-A 0 087 616, EP-A 0 087 677, EP-A 0 121 875, EP-A 0 151 287 and US 4,960,873.
  • Dyes of the formula B4 are known from US Pat. No. 5,216,139.
  • No. 5,132,412 describes dyes of the type of the formula B5.
  • Dyes of the formulas B6 and B7 are e.g. in US 3,981,883, DE-A 31 12 427, EP-A 0 064 221 or in Venkataraman "The Chemistry of Synthetic Dyes", volume 3, pages 444 to 447, or can be obtained by the methods mentioned therein.
  • Suitable methine dyes obey e.g. of the formula C.
  • Z 18 -CC 2 o-alkyl which is optionally substituted and can be interrupted by one or more oxygen atoms in ether function, optionally substituted phenyl or hydroxy
  • Z 19 is a 5-membered aromatic heterocyclic radical
  • Z 20 is hydrogen, cyano, carbamoyl, carboxyl or -CC 4 alkoxy carbonyl,
  • Z 21 is oxygen or a radical of the formula C (CN) 2 , C (CN) COOZ 23 or C (COOZ 23 ) 2 , where Z 23 each represents C 1 -C 8 -alkyl, which may be interrupted by 1 or 2 oxygen atoms in ether function is stands
  • Z 22 is hydrogen or -CC 4 alkyl.
  • substituted alkyl radicals occur in formula C, the following may be used as substituents, unless stated otherwise, for example phenyl, C 1 -C 4 -alkylphenyl, C 1 -C 4 -alkoxyphenyl, halophenyl,
  • the alkyl radicals generally have 1 or 2 substituents.
  • alkyl radicals which are interrupted by oxygen atoms in ether function occur in formula C, unless otherwise noted, preference is given to those alkyl radicals which are interrupted by 1 to 4 oxygen atoms, in particular 1 to 2 oxygen atoms, in ether function.
  • substituted phenyl or pyridyl radicals occur in formula C, the substituents, e.g. Ci-Cs-alkyl, Ci-Cs-alkoxy, halogen, in particular chlorine or bromine, or carboxyl.
  • the phenyl or pyridyl radicals generally have 1 to 3 substituents.
  • Z 19 radicals can be derived, for example, from components from the pyrrole, thiazole, thiophene or indole series.
  • Important Z 19 radicals are, for example, those of the formulas C 1 to C 4
  • Z 24 and Z 25 are the same or different and independently of one another are each hydrogen or -CC-alkyl, which is optionally substituted and can be interrupted by one or more oxygen atoms in ether function, optionally substituted phenyl or together with the nitrogen atom connecting them is a 5- or 6-membered saturated heterocyclic radical which may have further heteroatoms,
  • Z 26 is hydrogen, halogen, Ci-Cs-alkyl, optionally by
  • Z 27 are the same or different and are each independently hydrogen, hydroxy, optionally substituted by phenyl or C 4 -C 4 -alkylphenyl Ci-C ⁇ -alkyl, optionally substituted by phenyl or C 1 -C 4 -alkylphenyl Ci-Cs-alkoxy, C ⁇ - C 8 -alkanoylamino, C ⁇ -C 8 -alkylsulfonylamino or Ci-C ⁇ -mono- or dialkylaminosulfonylamino, Z 28 cyano, carbamoyl, C 1 -C 8 -mono- or dialkylcarbamoyl,
  • 4 -alkylthio optionally substituted by C ⁇ -C 4 alkyl or C ⁇ -C, Z 29 halogen are hydrogen, C 4 -alkyl, C 4 -alkoxy, C, 4 alkoxy-substituted phenyl or thienyl.
  • Such methine dyes are e.g. described in the older German patent application DE-A 44 03 083.
  • the process can be carried out particularly well in the presence of the dye of the formula A 3.1
  • the lightening of the textile materials is usually done using the pull-out or thermosol process.
  • the pull-out process usually works in aqueous liquors at temperatures of 90 to 135, usually around 130 ° C. In the case of application above 100 ° C, work must be carried out in an autoclave, a high-pressure device or a high-pressure machine.
  • Thermosol process is used at atmospheric pressure.
  • the textile material to be lightened is generally brought into an aqueous liquor at a temperature of 10 to 35 ° C., which contains the optically brightening compounds, optionally a blue or violet one
  • Shading dye or a mixture thereof and optionally an additive e.g. Contains dispersants, carboxylic acids or alkali donors and whose pH is usually 3 to 12, preferably 3 to 8.
  • the liquor ratio (weight ratio of textile material: liquor) is 1: 3 to 1:40, preferably 1: 5 to 1:20.
  • the bath is then heated to a temperature of 90 to 130 ° C., preferably 95 to 100 ° C., within 15 to 30 minutes and held at this temperature for 15 to 60 minutes. Then the lightened textile material is rinsed and dried.
  • the textile material to be lightened is usually padded with an aqueous liquor which contains the optical brightening substances, optionally a blue or violet shading dye or mixtures thereof and optionally an additive (see above).
  • the liquor intake is generally 50 to 100%.
  • the textile material is then dried and fixed at a temperature of 150 to 200 ° C for 5 to 60 seconds.
  • Dispersants which are colorless and which are stable against yellowing at temperatures of up to at least 210 ° C. are preferably used as dispersants.
  • Particularly suitable dispersants are e.g. Anionic or nonionic, in particular those from the class of ethylene oxide adducts with fatty alcohols, higher fatty acids or alkylphenols or ethylenediamine-ethylene oxide-propylene oxide adducts.
  • Particularly preferred dispersants are alkoxylation products which are based on aliphatic or alkylaromatic hydroxy, amine and aminohydroxy compounds under the brand names S nperonic® and Ukanil®, Dehypon®, Neopol®-Ethoxylate, Emulan®, Lutensol®, Plurafac® and Pluronic® or Elfapur® are commercially available.
  • S nperonic® and Ukanil® Dehypon®, Neopol®-Ethoxylate, Emulan®, Lutensol®, Plurafac® and Pluronic® or Elfapur® are commercially available.
  • Particularly preferred oxyalkylated phenols are oxyalkylated phenols of the general formulas IV and V
  • a and b are integers
  • a is in the range from 0 to 180, preferably from 0 to 125
  • b is in the range from 20 to 180, in particular from 35 to 125, where b ⁇ a;
  • M is an alkali metal, preferably Na or K and particularly preferably Na;
  • d 0 or 1.
  • VI VII with propylene oxide and subsequent reaction of the adduct with ethylene oxide or by reacting VI or VII with ethylene oxide.
  • the adducts can then be completely or partially reacted with chlorosulfonic acid or sulfur trioxide to give half-sulfuric acid and the half-esters obtained can be neutralized with alkaline agents.
  • the oxyalkylation can be carried out, for example, by the process described in US 2,979,528.
  • the sulfuric acid half-esters are prepared by reacting the oxyalkylation products with chlorosulfonic acid or sulfur trioxide, the amount of chlorosulfonic acid or sulfur trioxide being selected such that all free hydroxyl groups or only a certain percentage is sulfated. In the latter case, mixtures are formed from compounds of the formula IV or V which contain free and sulfated hydroxyl groups.
  • the half esters of sulfuric acid obtained in the reaction are converted into water-soluble salts.
  • the alkali metal salts for example the sodium or potassium salts, are advantageously considered as such.
  • Two equivalents are required in the case of chlorosulfonic acid, and one equivalent in the case of sulfur trioxide. The latter is used for moderately aqueous alkali metal hydroxide. The temperature should not exceed 70 ° C during neutralization.
  • the salts obtained can be isolated in the form of aqueous solutions or else as such and used in solid form.
  • Dispersants IV and V are preferred in which a is 0 to 2.5 on average, b is 25 to 250 on average and d is 0 to 0.5 on average. Dispersants IV and V are particularly preferred in which a is 0 to 2.5 on average, b is 50 to 100 on average and d is 0.5 on average.
  • Additional additives to be added are, for example, the biocides or water retention agents commonly used in the textile industry. Further additives to be added optionally are the copolymers of N-vinylpyrrolidone with 3-vinylpropionic acid described in EP-A 0 321 393.
  • a formulation which, in addition to water, in each case based on the weight of the preparation, 1 to 40% by weight, preferably 3 to 10% by weight, of the mixture of brightener and shading dye described in more detail above, 3 to 12 wt .-% anionic or nonionic
  • Dispersant 1 to 15% by weight copolymers of N-vinylpyrrolidone with vinyl acetate or vinyl propionate or mixtures thereof, and 1 to 25% by weight of other additives (e.g. water retention agents or biocides).
  • textile materials can be brightened with excellent white effects both in the pull-out and in the thermosol process.
  • the lightened materials show excellent fastness properties.
  • the individual predispersed substances having an optically brightening effect, and also the shading dyes, dispersants and / or other additives used, if appropriate, can be metered separately.
  • optically brightening compounds and optionally one or more of the shading dyes, dispersants and other additives described above are preferably used as formulations brought.
  • the present invention therefore furthermore relates to formulations comprising
  • Formulations according to the invention generally contain water 20 and, based in each case on the weight of the preparation, 1 to 40% by weight, preferably 3 to 25% by weight, of the mixtures of brightening compounds specified above, optionally 0.001 to 0, 1% by weight of shading dye, optionally 0.5 to 40% by weight of dispersant and 5 to 60% by weight, preferably 5 to 25 52% by weight, of additives.
  • Another object of the present invention is the use of the formulation according to the invention for lightening textile materials, in particular polyester or polyester mixtures.
  • the isomer distribution was as follows: I trans-cis, 95: 5 mol%; II p, o ', II mp'- II o, o', each over 95 mol% trans, determined in each case by 1 H-NMR spectroscopy.
  • polyester fabric was padded at room temperature with an aqueous liquor containing a total of 0.8 g / l of optically brightening compounds of the composition given below.
  • the pH was adjusted to 5.5 with acetic acid.
  • the fleet uptake was 60%.
  • the fabric was then dried at 110 ° C. for 20 s and then fixed at the temperature shown in Table 2 for 30 seconds.
  • the comparative tests V 2.13 to V 2.16 were carried out analogously to the examples according to the invention, but 1.5 g / l of a mixture of 70% by weight II o, p 'and 30% by weight II o, o' were used.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Inorganic Chemistry (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Diaphragms For Electromechanical Transducers (AREA)
  • Detergent Compositions (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé pour azurer des matériaux textiles par traitement avec des agents d'azurage optiques dans un bain aqueux, lequel se caractérise en ce que l'on utilise en tant qu'agent d'azurage optique 20 à 80 % en poids, par rapport à la somme de tous les composés ayant un effet d'azurage, d'un composé (I) dont 40 % en moles peuvent se présenter sous la forme d'un isomère cis, ainsi que 80 à 20 % en poids d'au moins un composé (II), sélectionné parmi les composés correspondant aux formules suivantes (II m, p'), (II p, o'), (II o, o') et (II p, p'), et 0 à 30 % en poids d'un composé correspondant à la formule (III), dans laquelle R représente un alkyle C4-C10. Le traitement est effectué en présence d'au moins un colorant de nuançage de la classe des anthraquinones, des colorants azoïques ou des colorants au méthine.
EP03717323A 2002-05-03 2003-04-30 Procede pour azurer des materiaux textiles Expired - Lifetime EP1504149B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10219993 2002-05-03
DE10219993A DE10219993A1 (de) 2002-05-03 2002-05-03 Verfahren zum Aufhellen von textilen Materialien
PCT/EP2003/004497 WO2003093565A2 (fr) 2002-05-03 2003-04-30 Procede pour azurer des materiaux textiles

Publications (2)

Publication Number Publication Date
EP1504149A2 true EP1504149A2 (fr) 2005-02-09
EP1504149B1 EP1504149B1 (fr) 2005-08-24

Family

ID=29265083

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03717323A Expired - Lifetime EP1504149B1 (fr) 2002-05-03 2003-04-30 Procede pour azurer des materiaux textiles

Country Status (15)

Country Link
US (1) US20050235429A1 (fr)
EP (1) EP1504149B1 (fr)
JP (1) JP2005529245A (fr)
KR (1) KR100973535B1 (fr)
CN (1) CN1333129C (fr)
AT (1) ATE302871T1 (fr)
AU (1) AU2003222312A1 (fr)
BR (1) BR0309642B1 (fr)
DE (2) DE10219993A1 (fr)
ES (1) ES2246470T3 (fr)
HR (1) HRPK20041141B3 (fr)
MX (1) MXPA04010130A (fr)
TW (1) TWI279468B (fr)
WO (1) WO2003093565A2 (fr)
ZA (1) ZA200409769B (fr)

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BR0317151A (pt) * 2002-12-10 2005-11-01 Ciba Sc Holding Ag Misturas de agentes de branqueamento fluorescentes
AR049538A1 (es) * 2004-06-29 2006-08-09 Procter & Gamble Composiciones de detergentes para lavanderia con colorante entonador eficiente
ES2322864T3 (es) 2004-09-23 2009-06-30 Unilever N.V. Composiciones de tratamiento de ropa sucia.
US20080034511A1 (en) * 2004-09-23 2008-02-14 Batchelor Stephen N Laundry Treatment Compositions
DE102005039971A1 (de) * 2005-08-23 2007-03-08 Basf Ag Flüssigwaschmittelformulierung
US20070174972A1 (en) * 2005-11-14 2007-08-02 Invista North America S.A R.I. Spandex having enhanced whiteness, and fabrics and garments comprising the same
WO2007082803A1 (fr) * 2006-01-18 2007-07-26 Ciba Holding Inc. Procédé de traitement de matériaux fibreux
CA2636869C (fr) * 2006-01-23 2013-05-28 Milliken & Company Compositions de lessive avec un colorant de thiazolium
US7642282B2 (en) * 2007-01-19 2010-01-05 Milliken & Company Whitening agents for cellulosic substrates
US20080177089A1 (en) 2007-01-19 2008-07-24 Eugene Steven Sadlowski Novel whitening agents for cellulosic substrates
WO2009074488A1 (fr) * 2007-12-10 2009-06-18 Basf Se Formulation de colorant et procédé pour le traitement de matériaux à base de fibres
BRPI0821867A2 (pt) * 2008-01-11 2015-07-28 Unilever Nv Composição de tratamento para lavagem de tecidos, processo doméstico para o tratamento de tecidos e corante de tiazol
ES2491104T3 (es) * 2010-04-29 2014-09-05 Unilever N.V. Colorantes azoicos bis heterocíclicos
US8715368B2 (en) 2010-11-12 2014-05-06 The Procter & Gamble Company Thiophene azo dyes and laundry care compositions containing the same
BR112013017496A2 (pt) * 2011-01-20 2016-09-27 Huntsman Adv Mat Switzerland formulações de agentes de branqueamento fluorescentes em forma dispersa
US9163146B2 (en) 2011-06-03 2015-10-20 Milliken & Company Thiophene azo carboxylate dyes and laundry care compositions containing the same
US9796952B2 (en) 2012-09-25 2017-10-24 The Procter & Gamble Company Laundry care compositions with thiazolium dye
CN112048075B (zh) * 2020-08-26 2022-11-08 盐城工学院 一种光致变色萘酰亚胺基Cd-MOF、其制备方法、光致变色印花浆及应用

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DE2929591A1 (de) * 1979-07-21 1981-02-05 Hoechst Ag Mischungen von optischen aufhellern
DE2929687A1 (de) * 1979-07-21 1981-02-12 Hoechst Ag Mischungen von optischen aufhellern
DE3104992A1 (de) * 1981-02-12 1982-08-26 Hoechst Ag, 6000 Frankfurt "mischungen von optischen aufhellern"
EP0240461B1 (fr) * 1986-04-02 1991-04-17 Ciba-Geigy Ag Mélanges d'agents de blanchiment optique
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EP0682145B1 (fr) * 1994-05-12 2004-08-25 Ciba SC Holding AG Traitement textile
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Also Published As

Publication number Publication date
TWI279468B (en) 2007-04-21
CN1650064A (zh) 2005-08-03
CN1333129C (zh) 2007-08-22
DE10219993A1 (de) 2003-11-20
WO2003093565A2 (fr) 2003-11-13
TW200407483A (en) 2004-05-16
HRPK20041141B3 (en) 2006-12-31
KR100973535B1 (ko) 2010-08-03
HRP20041141A2 (en) 2005-06-30
EP1504149B1 (fr) 2005-08-24
US20050235429A1 (en) 2005-10-27
MXPA04010130A (es) 2005-03-31
ZA200409769B (en) 2006-06-28
BR0309642A (pt) 2005-03-01
AU2003222312A1 (en) 2003-11-17
ES2246470T3 (es) 2006-02-16
KR20040106453A (ko) 2004-12-17
BR0309642B1 (pt) 2013-11-05
DE50301054D1 (de) 2005-09-29
AU2003222312A8 (en) 2003-11-17
WO2003093565A3 (fr) 2004-03-04
JP2005529245A (ja) 2005-09-29
ATE302871T1 (de) 2005-09-15

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