EP1725708B1 - Procede d'azurage optique de fibres synthetiques ou de fibres synthetiques en melange avec des fibres naturelles - Google Patents

Procede d'azurage optique de fibres synthetiques ou de fibres synthetiques en melange avec des fibres naturelles Download PDF

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EP1725708B1
EP1725708B1 EP05715882A EP05715882A EP1725708B1 EP 1725708 B1 EP1725708 B1 EP 1725708B1 EP 05715882 A EP05715882 A EP 05715882A EP 05715882 A EP05715882 A EP 05715882A EP 1725708 B1 EP1725708 B1 EP 1725708B1
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group
carbon atoms
radical
aliphatic
synthetic fibers
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EP1725708A2 (fr
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Karl Siemensmeyer
Dieter Weber
Andrea Misske
Heinz Heissler
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BASF SE
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BASF SE
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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
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • 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
    • D06L4/664—Preparations of optical brighteners; Optical brighteners in aerosol form; Physical treatment of optical 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
    • D06L4/671—Optical brightening assistants, e.g. enhancers or boosters

Definitions

  • the present invention relates to a process for optically brightening synthetic fibers or synthetic fibers in admixture with natural fibers, wherein the synthetic fibers or blends of the synthetic fibers with natural fibers are treated in a treatment bath containing optical brighteners to which a microemulsion has been added ,
  • optical brighteners are known for their property of giving a white color to textiles or plastics.
  • EP-A-33715 discloses an adjuvant mixture with various surfactants and its use for optically brightening polyester fiber materials.
  • EP-A-773 284 discloses microemulsions containing a non-water soluble solvent, an anionic surfactant and a branched fatty acid. They may also contain other components, such as brighteners, nonionic surfactants, water, and are used as laundry detergents for textile materials.
  • the EP 0 023 026 discloses compounds of general formula I. wherein the radicals R 1 and R 2 may be, for example, H, F, Cl, phenyl, CF 3 , alkyl or numerous other radicals, and wherein V is selected from
  • a disadvantage of using compounds of general formula I as optical brightener is that their yield is limited at low temperature, i. you need a lot of product to achieve the desired lightening effect.
  • EP-A 0 023 027 and EP-B2 0,032,917 , as well as in EP-B2 0 030 917 cited literature disclose the use of mixtures of two or more dicyanostyrylbenzene compounds for the optical whitening of polyesters.
  • the DE 102 19 993 A1 relates to a process for lightening textile materials, in which compounds of the general formula I, a dicyanostyrylbenzene compound and a compound of the general formula II, wherein R is selected from C 4-10 alkyl.
  • the optical whitening of textile materials is generally carried out by the exhaust or the Thermosolclar.
  • the textile material to be brightened is usually padded with an aqueous liquor which contains the optically brightening substances, optionally a blue or violet shading dye or mixtures thereof and optionally additives (see above).
  • the liquor pick-up is generally 30 to 100%.
  • the textile material is dried and fixed at a temperature of 150 to 200 ° C for 5 to 60 seconds.
  • thermosol process A disadvantage of the thermosol process is that the fixing temperature of 150 to 210 ° C, in particular from 170 to 190 ° C requires a high energy demand. At these high fixing temperatures, if necessary, additives or impurities adhering to the textile goods by previous treatment steps will smoke off and lead to gaseous emissions. Despite the high temperatures only a ring whitening is achieved in the thermosol process, which is inferior in the degree of whitening of a Ausziehfärbung. In the case of blends of the man-made fibers with natural fibers or with synthetic cellulose fibers, the natural or synthetic cellulose fiber may be browned.
  • Another known method is the exhaust process, which is usually carried out in aqueous liquor at temperatures of 90 to 135 ° C.
  • the leachable textile material is usually brought at a temperature of 10 to 50 ° C in an aqueous liquor, the optically brightening compounds, optionally a blue or violet Nuancierfarbstoff or a mixture thereof and optionally additives, such as dispersants, carboxylic acids or bases, and the pH is usually 3 to 12, preferably 3 to 8, is.
  • the liquor ratio (weight ratio of textile material: liquor) is 1: 1.5 to 1:40, preferably 1: 5 to 1:20.
  • the bath is then heated to a temperature of 95 to 135 ° C. within 15 to 60 minutes and held at this temperature for 15 to 60 minutes. Thereafter, the lightened textile material is rinsed and dried.
  • the HT process high temperature process is usually used.
  • the whitening process In order to sufficiently exceed the dyeing conversion temperature of the polyester, the whitening process must be performed at 130 ° C in order to achieve a brightening effect sufficient for practical use. Since the brightening takes place in an aqueous medium, it is necessary to work in an autoclave, a high-pressure apparatus or a high-pressure machine.
  • Such an aggregate is more expensive than an open unit, that the heating and cooling time and thus the machine occupancy is long and that the amount of energy required, especially for heating to 130 ° C is very high.
  • carriers are added to the whitening liquor, which reduce the dyeing conversion temperature by about 30 ° C.
  • Carriers are often formulations based on emulsifiers, sometimes solvents and the active component.
  • Active components are compounds based on liquid, halogenated benzene derivatives, alkylaromatic compounds, aromatic hydroxy compounds, aromatic alcohols, ketones, carboxylic acids and their esters, alkylphthalimides or substituted phenylglycols and their esters.
  • the most important active components are 1,2-dichlorobenzene, 1,2,4-trichlorobenzene, 2-phenylphenol, diphenyl, diphenyl ether, methyl, butyl or benzyl benzoates, methyl salicylates, dimethyl phthalates, phthalic acid-N-butylimides or chlorophenoxyethanol.
  • the Carrier process produces excellent whitening effects in a short brightening time with lower brightening temperature and thus lower energy consumption.
  • carriers can cause staining.
  • carriers are often carcinogenic.
  • a low-temperature process has been developed.
  • mixtures of nonionic and ionic surfactants with aliphatic or aromatic dicarboxylic acid esters are used instead of the carcinogenic carriers used. These mixtures are not fiber-active, but increase the solubility of the brightener in the dyeing liquor and thus allow the whitening at 98 to 110 ° C.
  • the mixtures of nonionic and ionic surfactants with aliphatic or aromatic dicarboxylic acid esters are also referred to as Diffusionaccelleratoren, ie, they accelerate the diffusion of the brightener of the dyeing liquor in the fiber.
  • the process has several disadvantages: When diluting, the diffusion accelerators undergo a swelling phase, which impairs the homogeneous distribution in the whitening bath. The resulting whiteness is inferior to that of carrier whitening. At whitening temperatures below 100 ° C, the whitening effect decreases rapidly. If acceptable white effects are achieved at 98 ° C, the resulting whiteness at 95 ° C is no longer sufficient for many requirements. In the textile finishing industry, however, temperatures above 95 ° C can often not be achieved in open aggregates, often in an aqueous medium.
  • the object of the present invention is to provide a brightening process which can be used in open aggregates, which achieves excellent whiteness, which is free of toxic or carcinogenic excipients, which avoids fleet inhomogeneities (in particular by swelling phases of surfactants) and which at temperatures around 95 ° C still produces excellent white effects.
  • This object is achieved according to the invention by a process for whitening synthetic fibers or mixtures of synthetic fibers with natural fibers, wherein the synthetic fibers or mixtures of synthetic fibers with natural fibers in a treatment bath containing optical brightener to which a microemulsion has been added, be treated.
  • microemulsions are already used in the dyeing of polyester in textile form as leveling agents. Dyes of polyester in textile form often become u-negal, uneven, stained. Such unevenness can be prevented or significantly reduced by adding microemulsions to the staining solutions.
  • the addition of the microemulsion stabilizes the disperse dye particles and controls the molecular transport process to the fiber and the dissolution process of the dye molecules in the polyester fiber.
  • Another task of the microemulsion is to control the dilution process when preparing the dye liquor so that no high-viscosity intermediate states are obtained.
  • microemulsion usable according to the invention includes nonionic surfactants, ionic surfactants, organic solubilizers and water.
  • microemulsions which can be used according to the invention can be prepared by mixing the corresponding components in any order.
  • the advantage of the microemulsion used according to the invention is its low viscosity at each mixing ratio with water.
  • the product can thus be used without problems in dosing systems.
  • the microemulsion is completely transparent.
  • the oil phase present in addition to the aqueous phase is thus finely distributed in the microemulsion so that no optical scattering is noticeable.
  • the mean size of the droplets of the disperse phase of the microemulsion used according to the invention can be determined according to the principle of quasi-elastic dynamic light scattering (the so-called z-mean droplet diameter d z of the unimodal analysis of the autocorrelation function).
  • the droplet size of the microemulsions used according to the invention are ⁇ 500 nm for d z .
  • the value for d z is preferably 50 nm to 300 nm, and the value for d z is particularly preferably 50 nm to 200 nm.
  • the process according to the invention makes it possible to optically lighten polyester, polyamides or mixtures of polyesters or polyamides with one another, wherein these may also be mixed with other synthetic or natural fibers.
  • Examples of other synthetic or natural fibers are cellulose fibers, polyacrylonitrile fibers, polyurethane fibers, acetate fibers or wool fibers.
  • the inventive method is particularly suitable for the optical brightening of polyester fibers or of mixtures of polyester fibers.
  • Polyesters are understood as meaning homopolymers, copolymers, blends and grafts of synthetic long-chain polyesters which, as an essential constituent, have recurring ester groups in the polymer backbone.
  • the polyesters used according to the invention are prepared from aromatic or aliphatic hydroxycarboxylic acids.
  • the aliphatic hydroxycarboxylic acids used in the polyesters according to the invention are optionally C 1-12 -carboxylic acids which are substituted by C 1-8 -alkyl chains and also contain at least one OH group in addition to the COOH group.
  • the said C 1-8 -alkyl chains are optionally substituted by further functional groups.
  • Hydroxycarboxylic acids are preferably selected from the group consisting of 2-hydroxyacetic acid, 2-hydroxypropionic acid, 3-hydroxypropionic acid, 4-hydroxybutyric acid, 5-Hydroxypentanoic acid, 6-hydroxyhexanoic acid, malic acid, tartaric acid and citric acid.
  • the aromatic or aliphatic hydroxycarboxylic acids which can be used according to the invention contain from 7 to 20 carbon atoms and at least one hydroxyl functionality; preference is given to using ortho, meta or parahydroxybenzoic acid in the polyesters which can be used according to the invention.
  • the usable polyesters include diacids and diols.
  • the diacids containing polyesters of the invention may be aliphatic or aromatic diacids of 4 to 18 carbon atoms.
  • dicarboxylic acids selected from the group consisting of phthalic acid, terephthalic acid, isophthalic acid, naphthalene-1,4-dicarboxylic acid, naphthalene-2,3-dicarboxylic acid, naphthalene-2,6-dicarboxylic acid, cyclohexanedicarboxylic acid, cyclohexanediacetic acid, diphenyl-4,4-dicarboxylic acid , Succinic, glutaric, adipic, azelaic, and sebacic acids or mixtures thereof.
  • the diacids containing in the polyester are particularly preferably selected from terephthalic acid or naphthaldiacetic acid or a mixture thereof.
  • the diols contained in the polyester which can be used according to the invention may be cycloaliphatic diols having 6 to 20 carbon atoms or aliphatic diols having 2 to 20 carbon atoms.
  • the diol contained in the polyester is selected from the group consisting of ethylene glycol, diethylene glycol, triethylene glycol, 1,4-cyclohexanedimethanol, propane-1,3-diol, butane-1,4-diol, pentane-1,5-diol, hexane -1,6-diol, 2-methylpentane-1,4-diol, 2,2,4-trimethylpentane-1,3-diol, hexane-1,3-diol, 2,2-bis (4-hydroxycyclohexyl) propane and 2,4-dihydroxy-1,1,3,3-tetramethylcyclobutane or mixtures thereof.
  • the polyester which can be used according to the invention comprises ethylene glycol as the diol component.
  • polyester homopolymers of polyethylene terephthalate (PET) or mixtures of polyethylene terephthalate with other polyesters are used as polyester homopolymers of polyethylene terephthalate (PET) or mixtures of polyethylene terephthalate with other polyesters.
  • the molecular weight of the inventively employable polyester is preferably in the range of 2000 to 50,000 g / mol.
  • the polyesters which can be used according to the invention can be produced in any possible thread thickness, as well as in any form, i. as flake, fiber, yarn, twisted fabric, woven fabric, knitwear or nonwoven.
  • polyesters used according to the invention are carried out by methods known to those skilled in the art, see Encycl. Polym. Sci. Engng. 12, 1 to 313 and Houben-Weyl E20 / 2, 1405-1429, Ullmann (4.), 19, 61-88.
  • optical brighteners such compounds can be used in the process according to the invention, which are already known, for example from Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Volume A18, pages 156-161 ,
  • the process according to the invention is particularly suitable for the optical whitening of polyester fibers based on PET or mixtures of PET with other synthetic or natural fibers.
  • Preferred optical brighteners in the process according to the invention are 1,4-bis-dicyanostyrylbenzenes of the general formula X. or 1,4-bis-dicyanostyrylbenzenes of the general formula X in mixture with one another or with other optical brighteners which are free of ionic groups, or compounds of the general formula I or compounds of the general formula I in admixture with other optical brighteners which are free used by ionic groups.
  • the ortho-para-isomer, the ortho-meta-isomer or the meta-para-isomer or mixtures of two or three or all isomers with one another or mixtures of one, two or all three isomers with the ortho-ortho isomers or with a compound of the general formula I can be used in the process according to the invention.
  • optical brighteners and shading dyes are generally used as aqueous preparations.
  • Such preparations generally contain water and, based in each case on the weight of the preparation, from 1 to 40% by weight, preferably from 2 to 25% by weight, particularly preferably from 3 to 10% by weight, of the above-described mixture of brighteners and Nuancierfarbstoff and 1 to 60 wt .-%, preferably 3 to 56 wt .-%, particularly preferably 5 to 52 wt .-% of auxiliaries.
  • auxiliaries are, for example, anionic or nonionic dispersants, from the class of the ethylene oxide adducts with fatty alcohols, higher fatty acids or alkylphenols or ethylenediamine-ethylene oxide-propylene oxide adducts, or dispersants, as in DE-A-2 745 449 Copolymers of N-vinylpyrolidone with 3-vinylpropionic acid, water retention agents such as ethylene glycol, glycerol or sorbitol or biocides.
  • a brightener preparation comprising, in addition to water, in each case based on the weight of the preparation, 1 to 40 wt .-%, preferably 2 to 25 wt .-%, particularly preferably 3 to 10 wt .-%, the above closer 1 to 30 wt .-%, preferably 2 to 20 wt .-%, particularly preferably 3 to 12 wt .-% of anionic or nonionic dispersant and 1 to 50 wt .-%, preferably 1 to 35% by weight, particularly preferably 1 to 25% by weight, of further auxiliaries (for example water retention agents or biocides).
  • further auxiliaries for example water retention agents or biocides
  • the treatment bath containing optical brighteners may contain shading dyes.
  • Nuancierfarbstoffe suitable according to the invention are generally from the class of disperse, acid or vat dyes. These are common names.
  • the color index includes such dyes as, for example, Disperse Blue or Disperse Violet or Acid Blue or Acid Violet or Vat Blue or Vat Violet.
  • blue dyes from the class of anthraquinones are particularly suitable.
  • azo dyes are particularly suitable.
  • methine dyes are particularly suitable.
  • violanthrones are particularly suitable.
  • the inventive method is carried out at a temperature of 80 to 120 ° C, preferably from 90 to 110 ° C, more preferably from 95 to 100 ° C.
  • the process according to the invention is carried out over a period of from 10 to 300 minutes, preferably over a period of from 20 to 200 minutes, more preferably over a period of from 30 to 120 minutes.
  • the present invention relates to the use of the treatment bath according to the invention containing optical brighteners for the optical brightening of synthetic fibers or of mixtures of synthetic fibers with natural fibers.
  • the present invention also relates to a treatment bath, to which a microemulsion according to the invention has been added, for synthetic fibers or for synthetic fibers mixed with natural fibers containing water, optical brighteners and optionally shading dyes.
  • the present invention relates to the use of the microemulsion according to the invention in treatment baths containing optical brighteners for synthetic fibers or synthetic fibers mixed with natural fibers.
  • composition of the microemulsion used according to the invention (in% by weight): Castor oil ethoxylated with 40 EO 20 Oleic acid ethoxylated with 5 EO 10 oleic acid 5 diglycol 20 Glutaric di-n-butyl ester 25 water 20
  • the microemulsion used according to the invention is prepared by mixing the components in the appropriate amounts, the order of addition of the individual components having no influence on the effectiveness of the microemulsion.
  • the resulting whiteness levels are as follows: Without tools 128 Diffusion accelerator 1 128.5 Diffusion accelerator 2 128 microemulsion 133
  • the resulting whiteness levels are as follows: Without tools 130 Diffusion accelerator 1 132 Diffusion accelerator 2 133 microemulsion 136
  • the resulting whiteness levels are as follows: Without tools 131 Diffusion accelerator 1 134 Diffusion accelerator 2 134 microemulsion 137
  • the resulting whiteness levels are as follows: Without tools 123 Diffusion accelerator 1 124 Diffusion accelerator 2 124 microemulsion 132

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
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  • Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)

Claims (8)

  1. Procédé pour l'azurage optique de fibres synthétiques ou de mélanges de fibres synthétiques et de fibres naturelles, caractérisé en ce que les fibres synthétiques ou les mélanges de fibres synthétiques et de fibres naturelles sont traités dans un bain de traitement contenant des azurants optiques auquel on ajoute une microémulsion, la microémulsion comprenant les composants suivants :
    (a) comme composant A, 1 à 40 % en poids d'un composé, qui est formé par la réaction d'un composé a1 répondant à la formule générale III
    Figure imgb0029
     où R1, R2, R3 représentent, indépendamment les uns des autres, un radical aliphatique, aromatique ou araliphatique qui peut être substitué par au moins un groupe fonctionnel choisi dans le groupe comprenant les groupes hydroxy, éther, amino, thio, aldéhyde, céto, acide carbonique, ester, amido et un halogène,
    et R4 représentent, indépendamment les uns des autres, un atome d'hydrogène ou un radical aliphatique comprenant 1 à 15 atomes de carbone, un radical aromatique comprenant 6 à 15 atomes de carbone ou un radical araliphatique comprenant 7 à 15 atomes de carbone,
    avec un composé a2 répondant à la formule générale IV
    Figure imgb0030
     où R5 représentent, indépendamment l'un de l'autre, un atome d'hydrogène ou un radical aliphatique comprenant 1 à 15 atomes de carbone, un radical aromatique comprenant 6 à 15 atomes de carbone ou un radical araliphatique comprenant 7 à 15 atomes de carbone ;
    (b) comme composant B, 1 à 25 % en poids d'un composé, qui est formé par la réaction d'un composé b1 répondant à la formule générale V
    Figure imgb0031
     où R6 représente un radical aliphatique, aromatique ou araliphatique qui peut être substitué par au moins un groupe fonctionnel choisi dans le groupe comprenant les groupes hydroxy, éther, amino, thio, aldéhyde, céto, acide carbonique, ester, amido et un halogène ;
    avec un composé b2 répondant à la formule générale VI
    Figure imgb0032
     où R7 représentent, indépendamment l'un de l'autre, un atome d'hydrogène ou un radical aliphatique comprenant 1 à 15 atomes de carbone, un radical aromatique comprenant 6 à 15 atomes de carbone ou un radical araliphatique comprenant 7 à 15 atomes de carbone ;
    (c) comme composant C, 1 à 15 % en poids d'un composé répondant à la formule générale VII
    Figure imgb0033
     où R8 représente un radical aliphatique, aromatique ou araliphatique ;
    (d) comme composant D, 1 à 40 % en poids d'un composé répondant à la formule générale VIII
    Figure imgb0034
     où R9 représente un radical aliphatique, aromatique ou araliphatique et la valeur moyenne pour n est un nombre positif entier ou fractionnaire de 1 à 10 ;
    (e) comme composant E, 1 à 50 % en poids d'un composé répondant à la formule générale IX
    Figure imgb0035
     où R10 représente un radical aliphatique, aromatique ou araliphatique et la valeur moyenne pour m est un nombre positif entier ou fractionnaire de 0 à 10 ;
    et de l'eau comme agent de solubilisation, la somme des pourcentages en poids des composants A, B, C, D et E et de l'eau comme agent de solubilisation donnant 100 % en poids.
  2. Procédé selon la revendication 1, caractérisé en ce que le procédé est conduit à une température de 80 à 120° C.
  3. Procédé selon la revendication 1 ou 2, caractérisé en ce que du polyester, du polyamide ou des mélanges de polyesters ou de polyamides sont azurés optiquement entre eux ou avec d'autres fibres synthétiques ou naturelles.
  4. Procédé selon l'une quelconque des revendications 1 à 3, caractérisé en ce que la microémulsion renferme des tensioactifs non ionogènes, des tensioactifs ioniques, des agents de solubilisation organiques et de l'eau.
  5. Procédé selon l'une quelconque des revendications 1 à 4, caractérisé en ce que le bain de traitement renfermant des azurants optiques contient des colorants de nuançage.
  6. Utilisation d'un bain de traitement contenant des azurants optiques selon l'une quelconque des revendications 1 à 5 pour l'azurage optique de fibres synthétiques ou de mélanges de fibres synthétiques et de fibres naturelles.
  7. Bain de traitement, auquel on ajoute une microémulsion selon l'une quelconque des revendications 1 à 4, pour des fibres synthétiques
    ou pour des fibres synthétiques en mélange avec des fibres naturelles contenant de l'eau, des azurants optiques et, facultativement, des colorants de nuançage.
  8. Utilisation d'une microémulsion selon l'une quelconque des revendications 1 à 4 dans des bains de traitement contenant des azurants optiques pour des fibres synthétiques ou pour des fibres synthétiques en mélange avec des fibres naturelles.
EP05715882A 2004-03-11 2005-03-09 Procede d'azurage optique de fibres synthetiques ou de fibres synthetiques en melange avec des fibres naturelles Expired - Lifetime EP1725708B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004011957A DE102004011957A1 (de) 2004-03-11 2004-03-11 Verfahren zum optischen Aufhellen von synthetischen Fasern oder von synthetischen Fasern in Mischung mit natürlichen Fasern
PCT/EP2005/002496 WO2005088004A2 (fr) 2004-03-11 2005-03-09 Procede d'azurage optique de fibres synthetiques ou de fibres synthetiques en melange avec des fibres naturelles

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EP1725708B1 true EP1725708B1 (fr) 2007-07-18

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US (1) US20070204410A1 (fr)
EP (1) EP1725708B1 (fr)
CN (1) CN1930340A (fr)
AT (1) ATE367471T1 (fr)
BR (1) BRPI0508569A (fr)
DE (2) DE102004011957A1 (fr)
EA (1) EA200601658A1 (fr)
ES (1) ES2287904T3 (fr)
WO (1) WO2005088004A2 (fr)

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CN102977628A (zh) * 2012-12-20 2013-03-20 山东沾化奥仕化学有限公司 荧光增白剂er-ⅱ型的一锅合成法

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US20100230061A1 (en) * 2006-01-26 2010-09-16 Achim Kohler Process for Producing Optically Brightened Paper
US9338761B2 (en) * 2014-02-26 2016-05-10 Empire Technology Development Llc Presence-based device mode modification

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EP0033715A1 (fr) * 1980-01-31 1981-08-12 Ciba-Geigy Ag Adjuvant et son utilisation pour la teinture ou l'azurage optique de matières textiles en polyester
US5540740A (en) * 1995-09-06 1996-07-30 China Textile Institute Low temperature microemulsion dyeing process for polyester fibers
EP0773284A1 (fr) * 1995-11-10 1997-05-14 The Procter & Gamble Company Microémulsions à teneur élevée en tensio-actifs anioniques utilisant des acides gras ramifiés

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CN102977628A (zh) * 2012-12-20 2013-03-20 山东沾化奥仕化学有限公司 荧光增白剂er-ⅱ型的一锅合成法

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EP1725708A2 (fr) 2006-11-29
DE502005001069D1 (de) 2007-08-30
ES2287904T3 (es) 2007-12-16
EA200601658A1 (ru) 2007-02-27
WO2005088004A2 (fr) 2005-09-22
ATE367471T1 (de) 2007-08-15
DE102004011957A1 (de) 2005-09-29
BRPI0508569A (pt) 2007-08-14
WO2005088004A3 (fr) 2006-02-09
CN1930340A (zh) 2007-03-14
US20070204410A1 (en) 2007-09-06

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