WO2004016849A1 - Method of dyeing or printing cellulose-containing fibre materials using disperse dyes - Google Patents

Method of dyeing or printing cellulose-containing fibre materials using disperse dyes Download PDF

Info

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
Authority
WO
WIPO (PCT)
Prior art keywords
hydrogen
alkyl
halogen
alkoxy
substituted
Prior art date
Application number
PCT/EP2003/050356
Other languages
French (fr)
Inventor
Peter Scheibli
Original Assignee
Ciba Specialty Chemicals Holding Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ciba Specialty Chemicals Holding Inc. filed Critical Ciba Specialty Chemicals Holding Inc.
Priority to US10/522,666 priority Critical patent/US20060048308A1/en
Priority to AU2003262557A priority patent/AU2003262557A1/en
Priority to EP03787810A priority patent/EP1530658A1/en
Publication of WO2004016849A1 publication Critical patent/WO2004016849A1/en

Links

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
    • 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.

Abstract

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 watersoluble or water-dispersible polyester resin and a water-soluble or water-dispersible acrylate binder produces level dyeings and prints having good allround fastness properties and is advantageously suitable for cellulose-containing fibre blends, for example blends consisting of polyester and cellulose.

Description

Method of dyeing or printing cellulose-containing fibre materials using disperse dyes
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. In such procedures, 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. By contrast, 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.
An increase in the range of woven and knitted fabrics has resulted in the increased use of natural and synthetic fibres in fibre blends. The usage of natural raw materials, such as cotton, can be considerably reduced by using such blends, while at the same time the quality of the fabrics and their comfort in practical use can also be improved. The increasing use of a very great variety of fibre blends calls for the use of special dyeing procedures that need to take into consideration the properties of each of the fibre components and their behaviour in relation to dyes and accompanying dyeing chemicals.
There are basically two types of method known for dyeing fibre blends: the two-bath method, in which each component of the fibre blend is dyed separately, and 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. On the other hand, in most cases the one-bath method offers a substantial saving in terms of resources, such as water, energy and the chemicals used.
The need for and the spread, in particular, of fibre blends consisting of cellulose and polyester has grown steadily in recent years. 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.
There is consequently still a need for a simplified method that is suitable for both dyeing and printing cellulose-containing fibre materials, especially cellulose-containing fibre blends. It should be a one-bath method which dyes the different kinds of fibre simultaneously and produces especially level dyeings or prints that have good allround fastness properties, for example good fastness to light and good wet-fastness.
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.
Preferably, the disperse dyes used in the method according to the invention correspond to formula
Figure imgf000004_0001
wherein
Ri is halogen, nitro or cyano,
R2 is hydrogen, halogen, nitro or cyano,
R3 is hydrogen, halogen or cyano,
R4 is hydrogen, halogen, C C4alkyl or C C4alkoxy,
R5 is hydrogen, halogen or C2-C4alkanoylamino and
R6 and R7 are each independently of the other hydrogen, allyl, or CrC4alkyl unsubstituted or substituted by hydroxy, cyano, C C4alkoxy,
Figure imgf000004_0002
C2-C4alkanoyloxy,
C C alkoxycarbonyl, phenyl or by phenoxy,
Figure imgf000004_0003
wherein
R8 is hydrogen, phenyl or phenylsulfonyl, the benzene ring in phenyl and phenylsulfonyl being unsubstituted or substituted by C C4alkyl, sulfo or by d-C^lkylsulfonyloxy, R9 is unsubstituted or Cι-C alkyl-substituted amino or is hydroxy,
Rio s hydrogen or Cι-C4alkoxy, R11 s hydrogen, CrC4alkoxy, phenoxy or the radical -O-C6H5-SO2-NH-(CH2)3-O-C2H5, 12 s hydrogen, hydroxy or nitro and
Rl3 s hydrogen, hydroxy or nitro,
Figure imgf000004_0004
wherein
R14 is C-ι-C alkyl unsubstituted or substituted by hydroxy or by phenyl or is phenyl,
R15 is Cι-C4alkyl,
R16 is cyano,
R17 is a radical of formula -(CH2)3-0-(CH2)2-0-C6H5, phenyl, or C C4alkyl substituted by hydroxy or by phenyl,
R-I8 is halogen, nitro or cyano and
R19 is hydrogen, halogen, nitro, trifluoromethyl or cyano,
Figure imgf000005_0001
wherein
R20 s d-C4alkyl, R21 s Cι-C4alkyl unsubstituted or substituted by C C alkoxy and R22 s the radical -COOCH2CH2OC6H5 and R23 is hydrogen or R22 s hydrogen and R23 is -N=N-C6H5,
Figure imgf000005_0002
wherein the rings A and B are unsubstituted or mono- or poly-substituted by halogen,
Figure imgf000005_0003
wherein
R2 is C C4alkyl unsubstituted or substituted by hydroxy, C C4alkoxy, Cι-C alkoxy- d-Oialkoxy, C2-C4alkanoyloxy or by d-C4alkoxycarbonyl,
Figure imgf000006_0001
wherein
R25 s C C4alkyl, R26 s CrC4alkyl unsubstituted or substituted by CrC4alkoxy, R27 s hydrogen, C C4alkoxy or halogen and
R28 s hydrogen, nitro, halogen or phenylsulfonyloxy,
Figure imgf000006_0002
wherein
R29, R30, R31 and R32 are each independently of the others hydrogen or halogen,
R33 is hydrogen, halogen, C C4alkyl or C-ι-C alkoxy,
R34 is hydrogen, halogen or acylamino and
R35 and R36 are each independently of the other hydrogen, or C-ι-C4alkyl unsubstituted or substituted by hydroxy, cyano, acetoxy or by phenoxy, or the dye of formula
Figure imgf000007_0001
wherein
R37 is hydrogen or halogen,
Figure imgf000007_0002
wherein
R38 is hydrogen, C C4alkyl, tetrahydrofuran-2-yl, or a d-C alkoxycarbonyl radical unsubstituted or substituted in the alkyl moiety by d-C alkoxy,
Figure imgf000007_0003
wherein
R39 is hydrogen, or thiophenyl unsubstituted or substituted in the phenyl moiety by d-C alkyl or by C C4alkoxy,
R4o is hydrogen, hydroxy, amino, or phenylcarbonylamino wherein the phenyl moiety is unsubstituted or substituted by CτC4alkyl,
R4ι 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 R42 is phenyl unsubstituted or substituted in the phenyl moiety by halogen, C C alkyl or by Cι-C4alkoxy,
Figure imgf000008_0001
wherein
R 3 is hydrogen or Cι-C4alkyl,
R^ and R45 are each independently of the other hydrogen, halogen, nitro or cyano, R46 is hydrogen, halogen, d-C4alkyl or Cι-C4alkoxy, R47 is hydrogen, halogen or C2-C4alkanoylamino and
R48 and R49 are each independently of the other hydrogen, or CrC4alkyl unsubstituted or substituted by hydroxy, cyano, Cι-C alkoxy, Cι-C alkoxy-C C alkoxy, C2-C alkanoyloxy, C-ι-C4alkoxycarbonyl, phenyl or by phenoxy, or
Figure imgf000008_0002
wherein
R50 is hydrogen or C C4alkyl,
R51 is phenyl or phenylcarbonyl, in each of which the phenyl moiety may be substituted by
C C4alkyl,
R52 and R53 are each independently of the other hydrogen, C C4alkyl or C C4alkoxy and
RM is hydrogen or Cι-C4alkyl.
Examples of the disperse dyes used in the method according to the invention that may be mentioned include the dyes of formulae
Figure imgf000009_0001
Figure imgf000010_0001
Figure imgf000011_0001
Figure imgf000011_0002
Figure imgf000011_0003
N CH2)3-0-(CH2)2 0- w (3a),
Figure imgf000011_0004
Figure imgf000011_0005
Figure imgf000012_0001
Figure imgf000012_0002
Figure imgf000012_0003
Figure imgf000012_0004
Figure imgf000012_0005
Figure imgf000013_0001
Figure imgf000014_0001
Figure imgf000015_0001
Figure imgf000015_0002
Figure imgf000015_0003
Figure imgf000016_0001
Figure imgf000016_0002
Figure imgf000016_0003
Figure imgf000017_0001
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).
Very special preference is given to the disperse dyes of formulae (3b), (3c), (3d), (3e), (3f), (3g), (6a), (6c), (8c), (8d), (12a), (12b), (12c), (12d), (13b), (13d), (13e) and (14a).
Special preference is given likewise to the disperse dyes of formulae (1d), (1e), (1f), (1g), (1h), (1i), (1j), (1 k), (4a), (6b), (8a), (8b), (8c), (8d), (11 b), (13a), (13b), (13c), (13d), (13e) and (13f).
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, styrene derivatives or vinylphosphonic acid; polyamide derivatives; synthetic resin dispersions; vinyl-based mixed polymers; diamide/aldehyde precondensation products; mixed polymers containing N-vinyllactam, and butadiene-based polymers. 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.
Suitable water-soluble or water-dilutable/water-dispersible 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 (in the form of a dry mass) is, e.g., from 4:1 to 1 :1 , preferably from 2:1 to 1 :1.
It is also possible, in addition, to use 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. Preferably, 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
\ 3 CH- - OH 0= I CH~ -OH
Figure imgf000019_0001
and especially N-methylol derivatives of nitrogen-containing compounds, e.g. non-etherified or etherified melamine-formaldehyde condensation products or N-methylolurea compounds.
The compounds of formulae
Figure imgf000020_0001
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.
Examples of such N-methylolurea compounds include unmodified and modified N-methylol- hydroxyethyleneurea products, for example the compounds of formula
Figure imgf000020_0002
CH3 H3COH 2C - NHCO - N - CH 2- C - CH(OH) - NHCONH - CH pCH 3 , and methylolation products CH2OH CH3
based on propyleneurea or ethyleneurea-melamine.
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).
If desired, 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 Textilhilfsmittelkatalog 1991 , Konradin Verlag R. Kohlhammer, Leinfelden-Echterdingen 1991. Examples of suitable crosslinking catalysts include inorganic acids, e.g. phosphoric acid; Lewis acids, e.g. zinc chloride, zirconium oxychloride, NaBF4, AICI3, MgCI2; ammonium salts, e.g. ammonium sulfate, ammonium chloride; and hydrohalides, especially hydrochlorides of organic amines, e.g. CH3-CH2-CH2-NH-CH3 . 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.
In order to increase the softness of the dyed or printed fibre material and thus obtain a certain handle, 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. When the treatment and dyeing are carried out simultaneously, 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. Advantageously, with that aftertreatment, any washing and rinsing steps can be avoided.
The pretreatment liquor, like the aftertreatment 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.
When the treatment with the aqueous composition is carried out as a pretreatment, prior to the dyeing or printing step, 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.
When an aftertreatment with the aqueous composition is optionally carried out following the dyeing or printing step, 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.
It is advantageous to convert the disperse dyes employed into a dye preparation before use. For that purpose, 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. For example, 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.
In the case of printing, 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.
Printing can also be carried out according to the inkjet printing method. In the past years there has been a significant increase in importance in the use of 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. For that purpose, mainly the continuous inkjet method and the drop-on-demand method are used. In 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. In the drop-on-demand method, however, 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). For the method according to the invention, preference is given to printing according to the continuous inkjet method or the drop-on-demand method. The preparation of the necessary disperse dye inks and the printing method procedure are described, for example, in US-A-6 284 004.
In addition to comprising the components indicated above, the pretreatment liquor or the dye composition may comprise further components, e.g. 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. In addition, 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.
The following Examples are intended to illustrate the invention without limiting the invention to the Examples specifically given. Example 1 : a) 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:
100 g/l of acrylate binder (ALCOPRINT® PB-HC),
10 g/l of methylol-melamine crosslinking resin (ALCOPRINT® PFL),
50 g/l of wash-fast softener (ULTRATEX® FSA),
100 g/l of water-soluble polyester resin (Worlee®Pol 192)
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.
b) 10 g of the fabric pretreated according to a) are introduced into 100 ml of a dye liquor containing
0.1 g of the disperse dye of formula (4b),
0.1 g of dispersing agent (UNIVADIN® DP),
0.1 g of deaerating agent (ALBEGAL® FFD) and
0.1 g of ammonium sulfate,
adjusted to pH 4.5 using dilute acetic acid, and heated to 130°C in a pressure vessel. After 30 minutes at 130°C, the liquor is cooled, and the dyed goods are removed, cold-rinsed, washed off for 15 minutes at 95°C in the presence of a wetting agent, rinsed again, dried, and finished by dry heat fixing (30 seconds at 180°C).
An orange dyeing exhibiting a high degree of levelness and good allround fastness properties is obtained.
Example 2:
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:
100 g/l of acrylate binder (ALCOPRINT® PB-HC), 10 g/l of methylol-melamine crosslinking resin (ALCOPRINT® PFL),
100 g/l of water-soluble polyester resin (Worlee®Pol 192) 14.3 g/l of dye formulation, containing 43% by weight of a finely ground active substance of formula (4b).
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 4:
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.
Example 5:
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:
100 g/l of acrylate binder (ALCOPRINT® PB-HC), 10 g/l of methylol-melamine crosslinking resin (ALCOPRINT® PFL),
100 g/l of water-soluble polyester resin (Worlee®Pol 192) 14.3g/l of dye formulation containing 43% by weight of a finely ground active substance of formula (12a). 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. The fabric is then 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:
100 g/l of acrylate binder (ALCOPRINT® PB-HC), 20 g/l of methylol-melamine crosslinking resin (ALCOPRINT® PFL), 100 g/l of water-soluble polyester resin (Worlee®Pol 192).
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 6:
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.
Example 7:
By proceeding as described in Example 1 , and using the following formulation for the pretreatment (Step a)):
24 g/l of acrylate thickener (ALCOPRINT® PTF), 100 g/l of acrylate binder (ALCOPRINT® PB-HC),
50 g/l of wash-fast softener (ULTRATEX® FSA), 100 g/l of water-soluble polyester resin (Worlee®Pol 192),
5 g/l of 30% ammonium hydroxide, applying the printing paste using a screen printing stencil, and then drying the impregnated fabric for 2 minutes at 120°C, condensing the applied polymer matrix for a further 2 minutes at 180°C, and subsequently dyeing the fabric as described under b) in Example 1 , 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. Examples 8 to 59:
By proceeding as described in Example 1 but using, instead of the dye of formula (4b), one of the dyes of formulae (1a), (1 b), (1c), (1d), (1e), (1f), (1g), (1 h), (1 i), (1j), (1 k), (2a), (2b), (2c), (2d), (2e), (2f), (2g), (3a), (3b), (3c), (3d), (3e), (3f), (3g), (4a), (5a), (6a), (6b), (6c), (7), (8a), (8b), (8c), (8d), (9a), (9b), (10a), (11a), (11 b), (11c), (12a), (12b), (12c), (12d), (13a), (13b), (13c), (13d), (13e), (13f) and (14a), there are likewise obtained dyeings in the colour shades of the respective dyes that exhibit a high degree of levelness and good allround fastness properties.
Examples 60 to 111 :
By proceeding as described in Example 2, but using instead of the dye of formula (4b) one of the dyes of formulae (1a), (1 b), (1c), (1d), (1e), (1f), (1g), (1 h), (1 i), (1j), (1 k), (2a), (2b), (2c), (2d), (2e), (2f), (2g), (3a), (3b), (3c), (3d), (3e), (3f), (3g), (4a), (5a), (6a), (6b), (6c), (7), (8a), (8b), (8c), (8d), (9a), (9b), (10a), (11a), (11 b), (11c), (12a), (12b), (12c), (12d), (13a), (13b), (13c), (13d), (13e), (13f) and (14a), there are likewise obtained dyeings in the colour shades of the respective dyes that exhibit a high degree of levelness and good allround fastness properties.
Examples 112 to 163:
By proceeding as described in Example 3, but using instead of the dye of formula (4b) one of the dyes of formulae (1a), (1 b), (1c), (1d), (1e), (1f), (1g), (1 h), (1 i), (1j), (1 k), (2a), (2b), (2c), (2d), (2e), (2f), (2g), (3a), (3b), (3c), (3d), (3e), (3f), (3g), (4a), (5a), (6a), (6b), (6c), (7), (8a), (8b), (8c), (8d), (9a), (9b), (10a), (11a), (11 b), (11c), (12a), (12b), (12c), (12d), (13a), (13b), (13c), (13d), (13e), (13f) and (14a), there are likewise obtained dyeings in the colour shades of the respective dyes that exhibit a high degree of levelness and good allround fastness properties.
Examples 164 to 215:
By proceeding as described in Example 4, but using instead of the dye of formula (4b) one of the dyes of formulae (1a), (1 b), (1c), (1d), (1e), (1f), (1g), (1 h), (1 i), (1j), (1 k), (2a), (2b), (2c), (2d), (2e), (2f), (2g), (3a), (3b), (3c), (3d), (3e), (3f), (3g), (4a), (5a), (6a), (6b), (6c), (7), (8a), (8b), (8c), (8d), (9a), (9b), (10a), (11a), (11 b), (11c), (12a), (12b), (12c), (12d), (13a), (13b), (13c), (13d), (13e), (13f) and (14a), there are likewise obtained dyeings in the colour shades of the respective dyes that exhibit a high degree of levelness and good allround fastness properties.
Examples 216 to 267:
By proceeding as described in Example 5, but using instead of the dye of formula (4b) one of the dyes of formulae (1a), (1 b), (1c), (1d), (1e), (1f), (1g), (1 h), (1 i), (1j), (1 k), (2a), (2b), (2c), (2d), (2e), (2f), (2g), (3a), (3b), (3c), (3d), (3e), (3f), (3g), (4a), (4b), (5a), (6a), (6b), (6c), (7), (8a), (8b), (8c), (8d), (9a), (9b), (10a), (11a), (11b), (11c), (12b), (12c), (12d), (13a), (13b), (13c), (13d), (13e), (13f) and (14a), there are likewise obtained dyeings in the colour shades of the respective dyes that exhibit a high degree of levelness and good allround fastness properties.
Examples 268 to 319:
By proceeding as described in Example 6, but using instead of the dye of formula (4b) one of the dyes of formulae (1a), (1 b), (1c), (1d), (1e), (1f), (1g), (1 h), (1 i), (1j), (1 k), (2a), (2b), (2c), (2d), (2e), (2f), (2g), (3a), (3b), (3c), (3d), (3e), (3f), (3g), (4a), (4b), (5a), (6a), (6b), (6c), (7), (8a), (8b), (8c), (8d), (9a), (9b), (10a), (11a), (11 b), (11c), (12b), (12c), (12d), (13a), (13b), (13c), (13d), (13e), (13f) and (14a), there are likewise obtained dyeings in the colour shades of the respective dyes that exhibit a high degree of levelness and good allround fastness properties.
Examples 320 to 371 :
By proceeding as described in Example 7, but using instead of the dye of formula (4b) one of the dyes of formulae (1a), (1 b), (1c), (1d), (1e), (1f), (1g), (1 h), (1 i), (1j), (1 k), (2a), (2b), (2c), (2d), (2e), (2f), (2g), (3a), (3b), (3c), (3d), (3e), (3f), (3g), (4a), (5a), (6a), (6b), (6c), (7), (8a), (8b), (8c), (8d), (9a), (9b), (10a), (11 a), (11 b), (11c), (12a), (12b), (12c), (12d), (13a), (13b), (13c), (13d), (13e), (13f) and (14a), there are likewise obtained dyeings in the colour shades of the respective dyes that exhibit a high degree of levelness and good allround fastness properties.

Claims

What is claimed is:
1. A method of dyeing or printing cellulose-containing fibre material using a disperse dye, which 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.
2. A method according to claim 1 , wherein the disperse dye corresponds to formula
Figure imgf000030_0001
wherein
Ri is halogen, nitro or cyano,
R2 is hydrogen, halogen, nitro or cyano,
R3 is hydrogen, halogen or cyano,
R4 is hydrogen, halogen, C C4alkyl or d-C4alkoxy,
R5 is hydrogen, halogen or C2-C4alkanoylamino and
R6 and R7 are each independently of the other hydrogen, allyl, or C C alkyl unsubstituted or substituted by hydroxy, cyano, C C4alkoxy,
Figure imgf000030_0002
C2-C4alkanoyloxy,
CrC4alkoxycarbonyl, phenyl or by phenoxy,
Figure imgf000030_0003
wherein
R8 is hydrogen, phenyl or phenylsulfonyl, the benzene ring in phenyl and phenylsulfonyl being unsubstituted or substituted by Cι-C4alkyl, sulfo or by Crdalkylsulfonyloxy,
R9 is unsubstituted or C C4alkyl-substituted amino or is hydroxy,
Rio is hydrogen or Cι-C alkoxy, Rn is hydrogen, C C alkoxy, phenoxy or the radical -0-C6H5-S02-NH-(CH2)3-0-C2H5, R12 is hydrogen, hydroxy or nitro and R13 is hydrogen, hydroxy or nitro,
Figure imgf000031_0001
wherein
Rι is C C4alkyl unsubstituted or substituted by hydroxy or by phenyl or is phenyl,
R15 is C C4alkyl,
R16 is cyano,
R17 is a radical of formula -(CH2)3-0-(CH2)2-0-C6H5, phenyl, or C C4alkyl substituted by hydroxy or by phenyl,
R18 is halogen, nitro or cyano and
R19 is hydrogen, halogen, nitro, trifluoromethyl or cyano,
Figure imgf000031_0002
wherein
R20 s C C4alkyl, R21 s C C alkyl unsubstituted or substituted by C C alkoxy and R22 s the radical -COOCH2CH2OC6H5 and R23 is hydrogen or R22 s hydrogen and R23 is -N=N-C6H5,
Figure imgf000031_0003
wherein the rings A and B are unsubstituted or mono- or poly-substituted by halogen,
Figure imgf000032_0001
wherein
R24 is C C alkyl unsubstituted or substituted by hydroxy, Cι-C4alkoxy, d-C4alkoxy- d-C4alkoxy, C2-C4alkanoyloxy or by d-C alkoxycarbonyl,
Figure imgf000032_0002
wherein
R25 s d-dalkyl,
R26 s d-C4alkyl unsubstituted or substituted by d-dalkoxy, R27 s hydrogen, d-C4alkoxy or halogen and R28 s hydrogen, nitro, halogen or phenylsulfonyloxy,
Figure imgf000032_0003
wherein
R29, R30, R31 and R32 are each independently of the others hydrogen or halogen, R33 is hydrogen, halogen, C C4alkyl or d-C4alkoxy,
R34 is hydrogen, halogen or acylamino and
R35 and R36 are each independently of the other hydrogen, or d-C alkyl unsubstituted or substituted by hydroxy, cyano, acetoxy or by phenoxy, or the dye of formula
Figure imgf000033_0001
wherein
R37 is hydrogen or halogen,
Figure imgf000033_0002
wherein
R38 is hydrogen, C C4alkyl, tetrahydrofuran-2-yl, or a d-C4alkoxycarbonyl radical unsubstituted or substituted in the alkyl moiety by C C alkoxy,
Figure imgf000033_0003
wherein R39 is hydrogen, or thiophenyl unsubstituted or substituted in the phenyl moiety by d-C4alkyl or by d-C alkoxy,
R o is hydrogen, hydroxy, amino, or phenylcarbonylamino wherein the phenyl moiety is unsubstituted or substituted by d-C alkyl,
R4ι is hydrogen, halogen, cyano, or thiophenyl, phenoxy or phenyl each of which is unsubstituted or substituted in the phenyl moiety by Cι-C4alkyl or by Cι-C4alkoxy and
R42 is phenyl unsubstituted or substituted in the phenyl moiety by halogen, Cι-C4alkyl or by
Cι-C4alkoxy,
Figure imgf000034_0001
wherein
R43 is hydrogen or Cι-C4alkyl,
R 4 and R are each independently of the other hydrogen, halogen, nitro or cyano,
R46 is hydrogen, halogen, C C4alkyl or d-C4alkoxy,
R47 is hydrogen, halogen or C2-C alkanoylamino and
R48 and R49 are each independently of the other hydrogen, or C1-C4alkyl unsubstituted or substituted by hydroxy, cyano, C C4alkoxy, Cι-C alkoxy-C C4alkoxy, C2-C4alkanoyloxy, d-C4alkoxycarbonyl, phenyl or by phenoxy, or
Figure imgf000034_0002
wherein
R50 is hydrogen or d-C4alkyl,
R51 is phenyl or phenylcarbonyl, in each of which the phenyl moiety may be substituted by d-dalkyl,
R52 and R53 are each independently of the other hydrogen, C C alkyl or d-C alkoxy and
Rea is hydrogen or d-dalkyl.
3. A method according to either claim 1 or claim 2, wherein the aqueous composition additionally comprises a crosslinking agent.
4. A method according to any one of claims 1 to 3, wherein the aqueous composition additionally comprises an agent imparting soft-handle properties.
5. A method according to any one of claims 1 to 4, wherein the treatment of the fibre material with the aqueous composition is carried out as a pretreatment prior to the material being brought into contact with the disperse dye.
6. A method according to claim 5, wherein the fibre material impregnated with the aqueous composition in a pretreatment step is dried and the applied polymer matrix is condensed.
7. A method according to any one of claims 1 to 6, wherein, after the dyeing procedure, a further treatment of the fibre material with the aqueous composition is carried out.
8. A method according to any one of claims 1 to 7, wherein the cellulose-containing fibre material is a fibre blend.
9. A method according to any one of claims 1 to 8, wherein the cellulose-containing fibre material is a fibre blend consisting of cellulose and polyester.
10. A method according to any one of claims 1 to 9, wherein the ratio by weight of polyester resin to acrylate binder in the composition is from 4:1 to 1 :1.
PCT/EP2003/050356 2002-08-12 2003-08-04 Method of dyeing or printing cellulose-containing fibre materials using disperse dyes WO2004016849A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US10/522,666 US20060048308A1 (en) 2002-08-12 2003-08-04 Method of dyeing or printing cellulose-containing fibre materials using disperse dyes
AU2003262557A AU2003262557A1 (en) 2002-08-12 2003-08-04 Method of dyeing or printing cellulose-containing fibre materials using disperse dyes
EP03787810A EP1530658A1 (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 (en) 2004-02-26

Family

ID=31725529

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/050356 WO2004016849A1 (en) 2002-08-12 2003-08-04 Method of dyeing or printing cellulose-containing fibre materials using disperse dyes

Country Status (5)

Country Link
US (1) US20060048308A1 (en)
EP (1) EP1530658A1 (en)
CN (1) CN100404751C (en)
AU (1) AU2003262557A1 (en)
WO (1) WO2004016849A1 (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012135622A1 (en) * 2011-03-31 2012-10-04 Celanese International Corporation Disperse dyeing of textile fibers
WO2013130429A1 (en) * 2012-02-29 2013-09-06 Celanese International Corporation Production of dyed cotton fibers
CN104947472A (en) * 2015-06-11 2015-09-30 常熟新锦江印染有限公司 Heat-transfer printing technology for pure cotton cloth
WO2018177652A1 (en) * 2017-03-29 2018-10-04 Huntsman Advanced Materials (Switzerland) Gmbh Process for printing cellulose containing textile fibre material
WO2018237027A1 (en) * 2017-06-22 2018-12-27 Zimmerman Keith Fabric treatment compositions and methods

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102127315A (en) * 2010-12-24 2011-07-20 上海宜连化工科技有限公司 Blue disperse dye composition with high light fastness and application thereof
WO2013130352A2 (en) 2012-03-01 2013-09-06 Ticona Llc Polyarylene sulfide fibers containing an emulsion copolymer coating
WO2013148295A2 (en) 2012-03-30 2013-10-03 Celanese International Corporation Disperse dyeing of textile fibers
WO2014063028A1 (en) 2012-10-19 2014-04-24 Celanese International Corporation Process for coloring textile materials
US20150275423A1 (en) * 2014-04-01 2015-10-01 Randolph L. Finley Ring dyed materials and method of making the same
CN110777549B (en) * 2019-11-11 2022-05-17 佛山市乐印涂料有限公司 Microcapsule slow-release cross-linking agent mucilage and preparation method and application thereof
CN110846774A (en) * 2019-11-29 2020-02-28 劲霸男装（上海）有限公司 Preparation method of anti-pilling fabric
CN111663345B (en) * 2020-05-21 2021-11-23 南通纺织丝绸产业技术研究院 Washing-free reactive dye printing treatment liquid and application thereof
CN111675798B (en) * 2020-06-03 2023-12-12 浙江五龙新材股份有限公司 Synthesis process and application of high-dispersity dispersing agent
CN114479561B (en) * 2022-03-11 2022-12-09 福建赛孔雀新材料科技有限公司 Smokeless digital printing ink and preparation method thereof

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 (en) * 1989-02-08 1990-08-23 Cassella Aktiengesellschaft Process for dyeing and printing blended fabrics made from polyester and natural fibre materials

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 (en) * 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 (en) * 1993-08-26 1995-03-07 Sumitomo Chem Co Ltd Red coloring composition containing benzodifuranone and coloring of hydrophobic material using the composition
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 (en) * 1989-02-08 1990-08-23 Cassella Aktiengesellschaft Process for dyeing and printing blended fabrics made from polyester and natural fibre materials

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012135622A1 (en) * 2011-03-31 2012-10-04 Celanese International Corporation Disperse dyeing of textile fibers
WO2013130429A1 (en) * 2012-02-29 2013-09-06 Celanese International Corporation Production of dyed cotton fibers
CN104947472A (en) * 2015-06-11 2015-09-30 常熟新锦江印染有限公司 Heat-transfer printing technology for pure cotton cloth
WO2018177652A1 (en) * 2017-03-29 2018-10-04 Huntsman Advanced Materials (Switzerland) Gmbh Process for printing cellulose containing textile fibre material
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 (en) * 2017-06-22 2018-12-27 Zimmerman Keith Fabric treatment compositions and methods
US10550513B2 (en) 2017-06-22 2020-02-04 Hbi Branded Apparel Enterprises, Llc Fabric treatment compositions and methods
CN111527257A (en) * 2017-06-22 2020-08-11 Hbi品牌服饰企业有限公司 Fabric treatment composition and method
CN111527257B (en) * 2017-06-22 2022-01-28 Hbi品牌服饰企业有限公司 Fabric treatment composition and method

Also Published As

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

Similar Documents

Publication Publication Date Title
WO2004016849A1 (en) Method of dyeing or printing cellulose-containing fibre materials using disperse dyes
US5131918A (en) Process for dyeing mixed anionic/cationic polyamide substrates with a specific type of vinyl sulfone dye
US4455147A (en) Transfer printing
US6497732B1 (en) Fiber-reactive polymeric dyes
US4599087A (en) Treatment of textile materials to improve the fastness of dyeings made thereon
EP0490676B1 (en) Process for preparing multi-colored dyed polyamide substrates
WO2014063028A1 (en) Process for coloring textile materials
CA1298041C (en) Fabric treatment to improve dyeability thereof
US20120246842A1 (en) Disperse dyeing of textile fibers
US6080687A (en) Method of dyeing anionic materials with pigment colors having a net cationic charge using a padding process
US5512064A (en) Process for modifying and dyeing modified fiber materials
CA1295438C (en) Textile printing and dyeing
US2719832A (en) Production of moistureproof coatings, impregnations, prints, and the like on fibrous materials and mixtures therefor
US5443630A (en) Inkjet single-phase reactive printing
GB2125837A (en) After treatment of reactive dyeings and optical brightenings
WO1993024701A1 (en) Process for fixation of dyes containing at least one polymerisable double bond by means of uv light
GB2105755A (en) Continuous dyeing of cellulosic textiles
Yang et al. Cotton fabric inkjet printing with acid dyes
KR19990013526A (en) Pigment dyeing method and pigment printing method
US5131913A (en) Production of pattern effects when dyeing or printing textile material in the absence of alkali or reducing agents: cationization and oxidized in a pattern before dyeing
US2663613A (en) Process for coloring nylon fiber
US20040194234A1 (en) Dyed and/or printed non-woven fabric
Gutjahr et al. Direct print coloration
CN1204711A (en) Pigment dyeing and pigment printing process
DE3422822A1 (en) COLORING PROCEDURE

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NI NO NZ OM PH PL PT RO RU SC SD SE SG SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2003787810

Country of ref document: EP

ENP Entry into the national phase

Ref document number: 2006048308

Country of ref document: US

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 10522666

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 20038194805

Country of ref document: CN

WWP Wipo information: published in national office

Ref document number: 2003787810

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 10522666

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP