WO2004016849A1 - Procede de coloration ou d'impression de matieres fibreuses contenant de la cellulose a l'aide de colorants de dispersion - Google Patents

Procede de coloration ou d'impression de matieres fibreuses contenant de la cellulose a l'aide de colorants de dispersion Download PDF

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Publication number
WO2004016849A1
WO2004016849A1 PCT/EP2003/050356 EP0350356W WO2004016849A1 WO 2004016849 A1 WO2004016849 A1 WO 2004016849A1 EP 0350356 W EP0350356 W EP 0350356W WO 2004016849 A1 WO2004016849 A1 WO 2004016849A1
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hydrogen
alkyl
halogen
alkoxy
substituted
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PCT/EP2003/050356
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English (en)
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Peter Scheibli
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Ciba Specialty Chemicals Holding Inc.
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Priority to EP03787810A priority Critical patent/EP1530658A1/fr
Priority to AU2003262557A priority patent/AU2003262557A1/en
Priority to US10/522,666 priority patent/US20060048308A1/en
Publication of WO2004016849A1 publication Critical patent/WO2004016849A1/fr

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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
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
    • D06P3/8228—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye
    • D06P3/8233—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye using dispersed 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
    • D06P1/52—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 synthetic macromolecular substances
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/525—Polymers of unsaturated carboxylic acids or functional derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • 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
    • D06P1/52—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 synthetic macromolecular substances
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/525—Polymers of unsaturated carboxylic acids or functional derivatives thereof
    • D06P1/5257—(Meth)acrylic acid
    • 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
    • D06P1/52—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 synthetic macromolecular substances
    • D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
    • D06P1/5271—Polyesters; Polycarbonates; Alkyd resins
    • 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
    • D06P1/52—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 synthetic macromolecular substances
    • D06P1/54—Substances with reactive groups together with crosslinking agents
    • 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
    • D06P3/6033—Natural or regenerated cellulose using dispersed dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/6033—Natural or regenerated cellulose using dispersed dyes
    • D06P3/6041—Natural or regenerated cellulose using dispersed dyes using specified dyes

Definitions

  • the present invention relates to a method of dyeing cellulose-containing fibre materials, especially fibre blends that contain cellulose, using disperse dyes.
  • Water-soluble reactive dyes which produce dyeings having good fastness-to-washing properties, are usually used to dye or print hydrophilic cellulose fibres.
  • the alcoholate groups of the cellulose fibre that are accessible on the surface react with the fibre-reactive groups of the reactive dyes, forming a covalent fibre/dye bond.
  • hydrophobic polyester fibres are dyed or printed using water-insoluble disperse dyes, which migrate from the aqueous dye preparation into the hydrophobic fibres. Since the properties of cellulose fibres and polyester fibres are different, the dyeing conditions to be employed will naturally also be different.
  • the two-bath method in which each component of the fibre blend is dyed separately
  • the one-bath method which has only one dyeing operation for all of the fibre components present.
  • the one-bath method is more complicated because, inter alia, the conditions need to be matched to the most sensitive of the fibre components, and the dyes chosen for the dyeing frequently have a different affinity for the fibres used.
  • the one-bath method offers a substantial saving in terms of resources, such as water, energy and the chemicals used.
  • Fibre blends consisting of cellulose and polyester are usually dyed with a mixture of reactive dyes and disperse dyes, that is to say with at least one suitable dye for each type of fibre.
  • the dyes from the different classes of dye that are to be combined with one another should, in addition to having a comparable affinity for the respective type of fibre, also have identical or at least similar shades, so as to ensure a uniform fabric appearance.
  • the only suitable method for printing fibre blends consisting of cellulose and polyester is pigment printing, in which a suitable binder resin ensures adhesion of the pigment to the fibre.
  • the present invention accordingly relates to a method of dyeing or printing cellulose- containing fibre materials using disperse dyes that comprises treating the fibre material with an aqueous composition comprising a water-soluble or water-dispersible polyester resin and a water-soluble or water-dispersible acrylate binder.
  • Suitable disperse dyes for the method according to the invention are those described under "Disperse Dyes" in the Colour Index, 3rd edition (3rd revision 1987 inclusive of Additions and Amendments up to No. 85).
  • Such dyes include, for example, carboxylic acid group-free and/or sulfonic acid group-free nitro, amino, aminoketone, ketoninime, methine, polymethine, diphenylamine, quinoline, benzimidazole, xanthene, oxazine and coumarin dyes and especially anthraquinone and azo dyes, such as mono- or dis-azo dyes.
  • the disperse dyes used in the method according to the invention correspond to formula wherein
  • Ri is halogen, nitro or cyano
  • R 2 is hydrogen, halogen, nitro or cyano
  • R 3 is hydrogen, halogen or cyano
  • R 4 is hydrogen, halogen, C C 4 alkyl or C C 4 alkoxy
  • R 5 is hydrogen, halogen or C 2 -C 4 alkanoylamino
  • R 6 and R 7 are each independently of the other hydrogen, allyl, or CrC 4 alkyl unsubstituted or substituted by hydroxy, cyano, C C 4 alkoxy, C 2 -C 4 alkanoyloxy,
  • R 8 is hydrogen, phenyl or phenylsulfonyl, the benzene ring in phenyl and phenylsulfonyl being unsubstituted or substituted by C C 4 alkyl, sulfo or by d-C ⁇ lkylsulfonyloxy, R 9 is unsubstituted or C ⁇ -C alkyl-substituted amino or is hydroxy,
  • Rl3 s hydrogen, hydroxy or nitro
  • R 14 is C- ⁇ -C alkyl unsubstituted or substituted by hydroxy or by phenyl or is phenyl,
  • R 15 is C ⁇ -C 4 alkyl
  • R 16 is cyano
  • R 17 is a radical of formula -(CH 2 ) 3 -0-(CH 2 ) 2 -0-C 6 H 5 , phenyl, or C C 4 alkyl substituted by hydroxy or by phenyl,
  • R- I8 is halogen, nitro or cyano
  • R 19 is hydrogen, halogen, nitro, trifluoromethyl or cyano
  • rings A and B are unsubstituted or mono- or poly-substituted by halogen
  • R 2 is C C 4 alkyl unsubstituted or substituted by hydroxy, C C 4 alkoxy, C ⁇ -C alkoxy- d-Oialkoxy, C 2 -C 4 alkanoyloxy or by d-C 4 alkoxycarbonyl, wherein
  • R25 s C C 4 alkyl, R26 s CrC 4 alkyl unsubstituted or substituted by CrC 4 alkoxy, R 27 s hydrogen, C C 4 alkoxy or halogen and
  • R28 s hydrogen, nitro, halogen or phenylsulfonyloxy
  • R 29 , R 30 , R 31 and R 32 are each independently of the others hydrogen or halogen
  • R 33 is hydrogen, halogen, C C 4 alkyl or C- ⁇ -C alkoxy,
  • R 34 is hydrogen, halogen or acylamino
  • R 35 and R 36 are each independently of the other hydrogen, or C- ⁇ -C 4 alkyl unsubstituted or substituted by hydroxy, cyano, acetoxy or by phenoxy, or the dye of formula
  • R 37 is hydrogen or halogen
  • R 38 is hydrogen, C C 4 alkyl, tetrahydrofuran-2-yl, or a d-C alkoxycarbonyl radical unsubstituted or substituted in the alkyl moiety by d-C alkoxy,
  • R 39 is hydrogen, or thiophenyl unsubstituted or substituted in the phenyl moiety by d-C alkyl or by C C 4 alkoxy,
  • R 4 o is hydrogen, hydroxy, amino, or phenylcarbonylamino wherein the phenyl moiety is unsubstituted or substituted by C ⁇ C 4 alkyl,
  • R 4 ⁇ is hydrogen, halogen, cyano, or thiophenyl, phenoxy or phenyl each of which is unsubstituted or substituted in the phenyl moiety by C C alkyl or by d-dalkoxy and R 42 is phenyl unsubstituted or substituted in the phenyl moiety by halogen, C C alkyl or by C ⁇ -C 4 alkoxy,
  • R 3 is hydrogen or C ⁇ -C 4 alkyl
  • R ⁇ and R 45 are each independently of the other hydrogen, halogen, nitro or cyano
  • R 46 is hydrogen, halogen, d-C 4 alkyl or C ⁇ -C 4 alkoxy
  • R 47 is hydrogen, halogen or C 2 -C 4 alkanoylamino
  • R 48 and R 49 are each independently of the other hydrogen, or CrC 4 alkyl unsubstituted or substituted by hydroxy, cyano, C ⁇ -C alkoxy, C ⁇ -C alkoxy-C C alkoxy, C 2 -C alkanoyloxy, C- ⁇ -C 4 alkoxycarbonyl, phenyl or by phenoxy, or
  • R 50 is hydrogen or C C 4 alkyl
  • R 51 is phenyl or phenylcarbonyl, in each of which the phenyl moiety may be substituted by
  • R 52 and R 53 are each independently of the other hydrogen, C C 4 alkyl or C C 4 alkoxy and
  • R M is hydrogen or C ⁇ -C 4 alkyl.
  • disperse dyes used in the method according to the invention include the dyes of formulae
  • the disperse dyes employed in the method according to the invention can be used on their own or in the form of a mixture of two or more disperse dyes. Preference is given to disperse dyes of formulae (1), (3), (4), (6), (8), (11), (12), (13) and (14), especially the disperse dyes of formulae (3), (6), (8), (12), (13) and (14).
  • the disperse dyes of formulae (1) to (14) are known or can be prepared analogously to known compounds according to standard procedures, for example by customary diazotization, coupling, addition and condensation reactions.
  • Suitable acrylate binders are the binders known from textile pigment printing and they include, for example, acrylic polymers, for example poly(meth)acrylates and mixed polymers of (meth)acrylates with suitable comonomers, for example acrylic acid, methacrylic acid, maleic acid, fumaric acid, itaconic acid, mesaconic acid, citraconic acid, vinylacetic acid, vinyloxyacetic acid, vinylpropionic acid, crotonic acid, aconitic acid, allylacetic acid, allyloxyacetic acid, allylmalonic acid, 2-acrylamido-2-methylpropanesulfonic acid, glutaconic acid or allylsuccinic acid, or with esters of such acids, (meth)acrylamide, N-vinylpyrrolidone, N-vinylformamide, N-vinylacetamide, (meth)acrolein, N-vinyl-N-methylacetamide, vinylcapro- lactam, styren
  • Suitable acrylate binders are soluble in aqueous medium or soluble in aqueous medium containing water- miscible organic solvents, if necessary with the addition of bases.
  • the said acrylate binders are preferably used in the form of an aqueous formulation.
  • Such acrylate binders are available commercially in acid form or in partially or fully neutralised form, e.g. Primal ® (Rohm & Haas), Neocryl ® (NeoResins), Carbocet ® (BF Goodrich), Joncryl ® (Johnson Polymers) or ALCOPRINT ® (Ciba Spezialitatenchemie) binders.
  • polyester resins are known from the coatings industry in which they are used as binders in the preparation of environmentally friendly, water-based paints.
  • Such polyester resins are described, for example, in US-A-4 054 614. They are preferably used in the form of an aqueous formulation and are available commercially, e.g. Dynapol ® (Degussa), Bayhydrol ® (Bayer) or Worlee ® Pol (Worlee) resins.
  • the ratio by weight of polyester resin to acrylate binder in the composition is, e.g., from 4:1 to 1 :1 , preferably from 2:1 to 1 :1.
  • crosslinking agents that react with the hydroxyl groups of the acrylate binder and polyester resin.
  • Such crosslinking agents can be applied to the fibre material simultaneously with or before or after the acrylate binder and polyester resin.
  • they are additionally present in the aqueous compositions used in accordance with the invention and are applied to the fibre material simultaneously with the acrylate binder and the polyester resin.
  • Suitable crosslinking agents include, for example, water-soluble melamine, formaldehyde- melamine, and formaldehyde-urea resins or precondensation products, such as trimethylolmelamine, hexamethylolmelamine or dimethylolurea or water-soluble formaldehyde (pre)condensation products with formamide, thiourea, guanidine, cyanamide, dicyandiamide and/or water-soluble organic sulfonates, e.g. naphthalenesulfonic acid sodium salt, or glyoxalic urea derivatives, e.g. the compound of formula
  • N-methylol derivatives of nitrogen-containing compounds e.g. non-etherified or etherified melamine-formaldehyde condensation products or N-methylolurea compounds.
  • non-etherified or etherified melamine-formaldehyde condensation products are examples of non-etherified or etherified melamine-formaldehyde condensation products.
  • the non-etherified or etherified N-methylolurea compounds are, for example, non-etherefied or subsequently etherified reaction products of formaldehyde with urea or urea derivatives, examples of suitable urea derivatives being cyclic ethylene- or propylene-ureas, which may also contain substituents such as hydroxyl groups in the alkylene group, urones and unsubstituted or substituted triazone resins.
  • N-methylolurea compounds include unmodified and modified N-methylol- hydroxyethyleneurea products, for example the compounds of formula
  • Crosslinking agents to which preference is given include unmodified and modified N-methylol-hydroxyethyleneurea compounds, methylolation products based on propyleneurea or ethyleneurea-melamine and especially non-etherified or etherified melamine-formaldehyde condensation products. It is also possible to use mixtures of two or more different water-soluble crosslinking agents, for example a mixture consisting of a non- etherified melamine-formaldehyde condensation product and an only partially etherified melamine-formaldehyde condensation product. Suitable crosslinking agents are known commercially, for example under the name ALCOPRINT ® (Ciba Spezialitatenchemie).
  • crosslinking catalysts can be used in addition.
  • Crosslinking catalysts suitable for the method according to the invention include, e.g., any agents customarily used as catalysts for imparting anti-crease and anti-shrink properties, such as are known from the Textilangesstoffkatalog 1991 , Konradin Verlag R. Kohlhammer, Leinfelden-Echterdingen 1991.
  • suitable crosslinking catalysts include inorganic acids, e.g. phosphoric acid; Lewis acids, e.g. zinc chloride, zirconium oxychloride, NaBF 4 , AICI 3 , MgCI 2 ; ammonium salts, e.g.
  • ammonium sulfate, ammonium chloride and hydrohalides, especially hydrochlorides of organic amines, e.g. CH 3 -CH 2 -CH 2 -NH-CH 3 . HCI. Preference is given to the use of ammonium salts or magnesium-containing Lewis acids and especially to the use of ammonium chloride or magnesium chloride.
  • the aqueous compositions used in accordance with the invention may additionally comprise an agent imparting soft-handle properties.
  • Soft-handle agents are known in the textile industry. They are non-ionic, anionic, cationic or amphoteric softeners. Emulsions of silicones, usually high-molecular-weight ,o dimethylpolysiloxane, are especially important. Soft-handle agents based on silicone emulsions are preferred. Such soft-handle agents are known commercially, for example under the name ULTRATEX ® (Ciba Spezialitatenchemie AG).
  • the cellulose-containing fibre materials are preferably fibre blends that contain cellulose, e.g. cellulose/polyester or cellulose/polyamide fibre blends, especially cellulose/polyester fibre blends.
  • the fibre materials can be in a very great variety of processing forms, e.g. in the form of fibres, filaments, yarn, scrap material, woven fabric or knitted fabric, preferably woven fabric or knitted fabric.
  • the treatment of the fibre material with the aqueous composition can be carried out before or simultaneously with the dyeing or printing step.
  • the dyeing composition for example the dye liquor or printing paste, additionally contains the above-mentioned components, such as acrylate binder and polyester resin, present in the aqueous composition.
  • Preference is given to carrying out the treatment with the aqueous composition before the material is brought into contact with the disperse dye, as a pretreatment prior to the actual dyeing or printing step.
  • a further preferred embodiment comprises, in addition to the first treatment which is carried out prior to or simultaneously with the dyeing or printing step, a further treatment with the aqueous composition, which is a finishing treatment carried out following the dyeing or printing step.
  • a further treatment with the aqueous composition which is a finishing treatment carried out following the dyeing or printing step.
  • any washing and rinsing steps can be avoided.
  • the pretreatment liquor can be applied to the fibre material in a variety of ways, for example according to the exhaust method and preferably by the pad- dyeing method.
  • the fibre material impregnated with the pretreatment liquor is advantageously subjected to a drying step, for example for from 0.5 to 10 minutes at from 80 to 140°C, especially for from 1 to 4 minutes at from 100 to 120°C, and then the condensation of the polymer matrix applied to the fibres is carried out, for example, for from 0.5 to 10 minutes at from 140 to 210°C, especially for from 0.5 to 4 minutes at from 150 to 180°C.
  • the fibre material impregnated with the aftertreatment liquor is advantageously subjected to a drying step, for example for from 0.5 to 10 minutes at from 80 to 140°C, especially for from 1 to 4 minutes at from 100 to 120°C, and then the condensation of the polymer matrix applied to the fibres is carried out, for example, for from 0.5 to 10 minutes at from 140 to 210°C, especially for from 0.5 to 4 minutes at from 150 to 180°C.
  • the aqueous composition used in accordance with the invention contains the above- mentioned components (as a dry mass) for example in the amounts indicated below based on the weight of the treatment liquor : acrylate binder: from 2 to 20% by weight, preferably from 5 to 20% by weight polyester resin: from 2 to 20% by weight, preferably from 5 to 20% by weight crosslinking agent: from 0 to 5% by weight softener: from 0 to 10% by weight
  • the cellulose-containing fibre materials can be dyed with the disperse dyes according to customary methods known for dyeing polyester fibres, for example according to the thermosol method, the exhaust method or continuous method.
  • the exhaust method is preferred.
  • the liquor ratio depends on the parameters of the apparatus, the substrate and the form of presentation, but can be selected from within a wide range, for example within a range of from 1 :4 to 1 :100; preferably it is within a range of from 1 :6 to 1 :25.
  • the dye is ground so that its average particle size is from 0.1 to 10 microns.
  • the grinding can be carried out in the presence of dispersing agents.
  • the dried dye is ground with a dispersing agent, or is kneaded into paste form with a dispersing agent and then dried in vacuo or by atomising.
  • the resulting preparations can be used to prepare printing pastes and dye baths after the addition of water.
  • the customary thickeners will be employed, e.g. modified or non- modified natural products, for example alginates, British gum, gum arabic, crystal gum, locust bean flour, tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
  • modified or non- modified natural products for example alginates, British gum, gum arabic, crystal gum, locust bean flour, tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
  • Printing can also be carried out according to the inkjet printing method.
  • inkjet printing methods for the production of printed textile materials.
  • Such a method involves individual droplets of ink being sprayed onto the substrate in a controlled manner from a nozzle.
  • the continuous inkjet method the droplets are produced continuously, the droplets not required for the printing operation being discharged into a receptacle and usually recycled.
  • the droplets are produced and used for printing as required, that is to say, droplets are produced only when necessary for the printing operation.
  • the droplets can advantageously be produced, for example, by means of a piezo inkjet head or by means of thermal energy (the so-called bubble jet).
  • a piezo inkjet head or by means of thermal energy (the so-called bubble jet).
  • thermal energy the so-called bubble jet.
  • the preparation of the necessary disperse dye inks and the printing method procedure are described, for example, in US-A-6 284 004.
  • the pretreatment liquor or the dye composition may comprise further components, e.g. stabilisers, such as UV absorbers, light stabilisers, antioxidants etc..
  • stabilisers such as UV absorbers, light stabilisers, antioxidants etc.
  • the treatment according to the invention renders the cellulose fibres dyeable by disperse dyes.
  • Dyeing and printing methods for fibre blends are consequently substantially simplified. It is thus possible for all components of the fibre blends to be dyed simultaneously using dyes from one class of dyes (disperse dyes), that is to say, in addition to the polyester component of a cellulose/polyester fibre mixture being dyed, the cellulose component will also be dyed without any problem using the same dye.
  • the method according to the invention furthermore meets the important requirement that, when it is used for fibre blends, the dyeability of the polyester component is fully retained.
  • the matrix of acrylate binder and polyester resin applied to the fibres survives, undamaged, the conditions of a conventional high-temperature dyeing procedure for polyester, e.g. 30 minutes at 130°C.
  • the dyeings or prints obtained using the method according to the invention have very good fastness to light and good wet-fastness properties, such as fastness to washing, to water, to seawater, to cross-dyeing and to perspiration. Also, level dyeings with respect to the fibres and the areas dyed are obtained.
  • Example 1 A woven textile fabric consisting of 100% bleached cotton is pad-dyed with an aqueous liquor (liquor pick-up 70%) containing the following additives, each in the form of an aqueous formulation in the amounts indicated:
  • wash-fast softener (ULTRATEX ® FSA),
  • the impregnated fabric is then dried for 2 minutes at 120°C and the applied polymer matrix is condensed for a further 2 minutes at 180°C.
  • deaerating agent ALBEGAL ® FFD
  • Example 3 By proceeding as described in Example 1 but using, instead of a woven cotton fabric, a woven fabric consisting of a 50% cotton/50% polyester fibre blend, there is likewise obtained an orange dyeing that exhibits a high degree of levelness and good allround fastness properties.
  • Example 3
  • a woven textile fabric consisting of 100% bleached cotton is pad-dyed with an aqueous liquor (liquor pick-up 70%) containing the following additives, each in the form of an aqueous formulation in the amounts indicated:
  • ACOPRINT ® PB-HC 100 g/l of acrylate binder (ALCOPRINT ® PB-HC), 10 g/l of methylol-melamine crosslinking resin (ALCOPRINT ® PFL),
  • the impregnated fabric is then dried for 2 minutes at 120°C and the applied polymer matrix is condensed for a further 2 minutes at 180°C, then cold-rinsed, washed off for 5 minutes at 95°C and rinsed again.
  • a level orange cotton dyeing exhibiting a high degree of fastness to light and good fastness to water and to rubbing is obtained.
  • Example 3 By proceeding as described in Example 3 but using, instead of a woven cotton fabric, a woven fabric consisting of a 50% cotton/50% polyester fibre blend, there is likewise obtained an orange dyeing that exhibits a high degree of levelness and good allround fastness properties.
  • a woven textile fabric consisting of 100% bleached cotton is pad-dyed with an aqueous liquor (liquor pick-up 70%) containing the following additives, each in the form of an aqueous formulation in the amounts indicated:
  • ACOPRINT ® PB-HC 100 g/l of acrylate binder (ALCOPRINT ® PB-HC), 10 g/l of methylol-melamine crosslinking resin (ALCOPRINT ® PFL),
  • ACOPRINT ® PB-HC 100 g/l of acrylate binder
  • ACOPRINT ® PFL 20 g/l of methylol-melamine crosslinking resin
  • Worlee ® Pol 192 100 g/l of water-soluble polyester resin
  • the impregnated fabric is then dried for 2 minutes at 120°C and the applied polymer matrix is condensed for a further 2 minutes at 200°C, yielding, without further washing and rinsing steps, a level yellow cotton dyeing that exhibits a high degree of fastness to light and good fastness to water, to washing and to rubbing.
  • Example 5 By proceeding as described in Example 5 but using, instead of a woven cotton fabric, a woven fabric consisting of a 50% cotton/50% polyester fibre blend, there is likewise obtained an orange dyeing that exhibits a high degree of levelness and good allround fastness properties.
  • ACOPRINT ® PTF 24 g/l of acrylate thickener (ALCOPRINT ® PTF), 100 g/l of acrylate binder (ALCOPRINT ® PB-HC),
  • wash-fast softener ULTRATEX ® FSA
  • water-soluble polyester resin Worlee ® Pol 192
  • Example 8 there is likewise obtained an orange dyeing that exhibits a high degree of levelness and good allround fastness properties at the locations where dye has been applied using a screen printing stencil.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)

Abstract

La présente invention concerne un procédé de coloration ou d'impression de matières fibreuses contenant de la cellulose à l'aide de colorants de dispersion. Ledit procédé consiste à traiter la matière fibreuse à l'aide d'une composition aqueuse comprenant une résine de polyester hydrosoluble ou hydrodispersable et d'un liant d'acrylate hydrosoluble ou hydrodispersable. Ledit procédé permet d'obtenir des unissons et des impressions présentant de bonnes propriétés de solidité générale et est particulièrement avantageux pour des mélanges de fibres contenant de la cellulose, par exemple pour des mélanges constitués de polyester et de cellulose.
PCT/EP2003/050356 2002-08-12 2003-08-04 Procede de coloration ou d'impression de matieres fibreuses contenant de la cellulose a l'aide de colorants de dispersion WO2004016849A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP03787810A EP1530658A1 (fr) 2002-08-12 2003-08-04 Procede de coloration ou d'impression de matieres fibreuses contenant de la cellulose a l'aide de colorants de dispersion
AU2003262557A AU2003262557A1 (en) 2002-08-12 2003-08-04 Method of dyeing or printing cellulose-containing fibre materials using disperse dyes
US10/522,666 US20060048308A1 (en) 2002-08-12 2003-08-04 Method of dyeing or printing cellulose-containing fibre materials using disperse dyes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP02405686.3 2002-08-12
EP02405686 2002-08-12

Publications (1)

Publication Number Publication Date
WO2004016849A1 true WO2004016849A1 (fr) 2004-02-26

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US (1) US20060048308A1 (fr)
EP (1) EP1530658A1 (fr)
CN (1) CN100404751C (fr)
AU (1) AU2003262557A1 (fr)
WO (1) WO2004016849A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012135622A1 (fr) * 2011-03-31 2012-10-04 Celanese International Corporation Colorant de dispersion de fibres textiles
WO2013130429A1 (fr) * 2012-02-29 2013-09-06 Celanese International Corporation Production de fibres de coton colorées
CN104947472A (zh) * 2015-06-11 2015-09-30 常熟新锦江印染有限公司 一种纯棉布的热转移印花工艺
WO2018177652A1 (fr) * 2017-03-29 2018-10-04 Huntsman Advanced Materials (Switzerland) Gmbh Procédé d'impression de cellulose contenant un matériau de fibre textile
WO2018237027A1 (fr) * 2017-06-22 2018-12-27 Zimmerman Keith Compositions de traitement de tissu et procédés associés

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102127315A (zh) * 2010-12-24 2011-07-20 上海宜连化工科技有限公司 一种高耐光牢度的蓝色分散染料组合物及其应用
WO2013130352A2 (fr) 2012-03-01 2013-09-06 Ticona Llc Fibres de polysulfure d'arylène contenant un revêtement polymère en émulsion
WO2013148295A2 (fr) 2012-03-30 2013-10-03 Celanese International Corporation Teinture dispersée de fibres textiles
WO2014063037A1 (fr) * 2012-10-19 2014-04-24 Celanese International Corporation Coloration dispersée de fibres textiles
US20150275423A1 (en) * 2014-04-01 2015-10-01 Randolph L. Finley Ring dyed materials and method of making the same
CN110777549B (zh) * 2019-11-11 2022-05-17 佛山市乐印涂料有限公司 一种微胶囊缓释交联剂胶浆及其制备方法和应用
CN110846774A (zh) * 2019-11-29 2020-02-28 劲霸男装（上海）有限公司 一种抗起毛起球面料的制备方法
CN111663345B (zh) * 2020-05-21 2021-11-23 南通纺织丝绸产业技术研究院 免水洗活性染料印花处理液及其应用
CN111675798B (zh) * 2020-06-03 2023-12-12 浙江五龙新材股份有限公司 一种高分散力分散剂的合成工艺及其应用
CN114479561B (zh) * 2022-03-11 2022-12-09 福建赛孔雀新材料科技有限公司 一种无烟数码印花墨水及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4231745A (en) * 1975-11-15 1980-11-04 Hoechst Aktiengesellschaft Process for pad-dyeing and printing fabrics made of cellulose and/or regenerated modified cellulose and optionally polyester fibers
US4299592A (en) * 1979-01-18 1981-11-10 Basf Aktiengesellschaft Printing of textile materials
WO1990009478A1 (fr) * 1989-02-08 1990-08-23 Cassella Aktiengesellschaft Procede de teinture et d'impression de tissus melanges en polyester et en fibres naturelles

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3510241A (en) * 1966-11-16 1970-05-05 Allied Chem Coloration of aromatic polyesters
JPS5029552B2 (fr) * 1972-07-25 1975-09-23
US4054614A (en) * 1976-02-23 1977-10-18 Celanese Corporation Water soluble polyester coating compositions
JPS56148981A (en) * 1980-03-25 1981-11-18 Donkurofuto Karaazu Ando Chem Sublimable dyestuff transfer printing method and composition
US4702742A (en) * 1984-12-10 1987-10-27 Canon Kabushiki Kaisha Aqueous jet-ink printing on textile fabric pre-treated with polymeric acceptor
JPH0762258A (ja) * 1993-08-26 1995-03-07 Sumitomo Chem Co Ltd ベンゾジフラノン含有赤色着色性組成物及びそれを用いる疎水性材料の着色方法
US5554734A (en) * 1994-06-20 1996-09-10 Ciba-Geigy Corporation AZO dyes containing a bridge member based on stibene and morpholino-substituted triazine
US6113656A (en) * 1995-01-17 2000-09-05 Milliken & Company Method of dyeing low pill polyester
TW515859B (en) * 1997-12-17 2003-01-01 Ciba Sc Holding Ag Process for ink-jet printing textile fibre materials

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4231745A (en) * 1975-11-15 1980-11-04 Hoechst Aktiengesellschaft Process for pad-dyeing and printing fabrics made of cellulose and/or regenerated modified cellulose and optionally polyester fibers
US4299592A (en) * 1979-01-18 1981-11-10 Basf Aktiengesellschaft Printing of textile materials
WO1990009478A1 (fr) * 1989-02-08 1990-08-23 Cassella Aktiengesellschaft Procede de teinture et d'impression de tissus melanges en polyester et en fibres naturelles

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012135622A1 (fr) * 2011-03-31 2012-10-04 Celanese International Corporation Colorant de dispersion de fibres textiles
WO2013130429A1 (fr) * 2012-02-29 2013-09-06 Celanese International Corporation Production de fibres de coton colorées
CN104947472A (zh) * 2015-06-11 2015-09-30 常熟新锦江印染有限公司 一种纯棉布的热转移印花工艺
WO2018177652A1 (fr) * 2017-03-29 2018-10-04 Huntsman Advanced Materials (Switzerland) Gmbh Procédé d'impression de cellulose contenant un matériau de fibre textile
US20200102699A1 (en) * 2017-03-29 2020-04-02 Huntsman Advanced Materials (Switzerland) Gmbh Process for Printing Cellulose Containing Textile Fibre Material
US11008700B2 (en) 2017-03-29 2021-05-18 Huntsman International Llc Process for printing cellulose containing textile fibre material
WO2018237027A1 (fr) * 2017-06-22 2018-12-27 Zimmerman Keith Compositions de traitement de tissu et procédés associés
US10550513B2 (en) 2017-06-22 2020-02-04 Hbi Branded Apparel Enterprises, Llc Fabric treatment compositions and methods
CN111527257A (zh) * 2017-06-22 2020-08-11 Hbi品牌服饰企业有限公司 织物处理组合物和方法
CN111527257B (zh) * 2017-06-22 2022-01-28 Hbi品牌服饰企业有限公司 织物处理组合物和方法

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AU2003262557A1 (en) 2004-03-03
US20060048308A1 (en) 2006-03-09
EP1530658A1 (fr) 2005-05-18
CN100404751C (zh) 2008-07-23
CN1675429A (zh) 2005-09-28

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