EP0638686A1 - Procédé et utilisation de colorants réactifs de dispersion pour teindre ou imprimer des textiles en coton ou en mélange coton/polyester - Google Patents

Procédé et utilisation de colorants réactifs de dispersion pour teindre ou imprimer des textiles en coton ou en mélange coton/polyester Download PDF

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Publication number
EP0638686A1
EP0638686A1 EP94112297A EP94112297A EP0638686A1 EP 0638686 A1 EP0638686 A1 EP 0638686A1 EP 94112297 A EP94112297 A EP 94112297A EP 94112297 A EP94112297 A EP 94112297A EP 0638686 A1 EP0638686 A1 EP 0638686A1
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EP
European Patent Office
Prior art keywords
group
groups
amino
methyl
hydroxyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP94112297A
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German (de)
English (en)
Inventor
Werner Hubert Dr. Russ
Andreas Dr. Schrell
Andreas Dr. Von Der Eltz
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Hoechst AG
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Hoechst AG
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Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0638686A1 publication Critical patent/EP0638686A1/fr
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642Compounds containing nitrogen
    • D06P1/6426Heterocyclic compounds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/66Natural or regenerated cellulose using reactive dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/82Textiles which contain different kinds of fibres
    • D06P3/8204Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8223Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
    • D06P3/8228Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye
    • D06P3/8233Textiles 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
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916Natural fiber dyeing
    • Y10S8/918Cellulose textile
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/921Cellulose ester or ether

Definitions

  • a method was therefore desirable for the future, textile fibers, preferably those that contain the base body of the ⁇ , ⁇ -glucose and the polyester at the same time, using only one class of dyes, i.e. without intermediate rinsing processes or changes in the pH value of the dyeing liquors.
  • the present invention therefore relates to a process for dyeing materials made from hydroxyl-containing fibers, such as cellulose fibers, or from mixed fiber materials made from hydroxyl-containing fibers and polyester fibers, which is characterized in that the hydroxyl-containing fiber material is a hydroxyl-containing fiber material modified with an amino group-containing compound and a fiber-reactive dye Disperse dye is used and the coloring in an aqueous, low-electrolyte or completely electrolyte-free medium and in the absence of an alkaline or alkali-donating agent, such as at a pH between 5 and 7, preferably between 5.5 and 6.5, and at Temperature between 100 and 210 ° C, preferably between 110 and 190 ° C, is carried out.
  • hydroxyl-containing fibers such as cellulose fibers
  • Dyeing processes are also understood to mean the printing processes customary in the art for printing on textile materials and dyeing using ink jet printers.
  • Modified fiber materials containing hydroxy groups which can be used in the process according to the invention are, for example, those described in Canadian Patent Nos. 1,267,490 and 2,084,585, in European Patent Application Publication No. 0 286 597 and in Japanese Patent Application Publication Hei -5-5279 are described, furthermore such fiber materials that with those in the German Laid-Open Patent Application No. 2,930,738 have been pretreated and modified as aftertreatment agents, and furthermore in particular hydroxy group-containing fiber materials which have been modified in accordance with the information in European Patent Application Publication No. 0 546 476 or with the compounds of the general formula (1) described below.
  • the information in the patent documents mentioned about the modified fiber materials and their production should be part of the disclosure of the present application.
  • ester group ER is a sulfato group of the formula -OSO3M, where M is hydrogen or an alkali metal, for example sodium, potassium or lithium, and the amino group-containing compound N is particularly preferred - ( ⁇ -sulfatoethyl) piperazine.
  • the compounds of the formula (1) can be prepared according to known procedures, as are described in numerous publications (see Houben-Weyl, Methods of Organic Chemistry, 4th edition, Volume E4, pages 82-88 and 192ff.) , for example by reacting an alkanediol which has a latent nitrogen-containing functional group in the side chain with phosgene in aqueous solution at a pH between 7 and 9 to produce the heterocycloaliphatic carbonates or, for example, by Reaction of aminoalkanols with phosgene in aqueous solution to the heterocycloaliphatic carbamic acid compounds (2-oxo-1,3-oxazolidines).
  • the modification of the fiber materials containing hydroxy groups with the compounds of the general formula (1) can be carried out analogously to the information in European patent application publication No. 0 546 476, for example in such a way that the compound of the formula (1) is dissolved in an aqueous, alkaline solution at a temperature between 60 and 200 ° C, preferably between 90 and 190 ° C, can act on the original hydroxy group-containing fiber material.
  • the compound of the general formula (1) is present in the alkaline aqueous solution in a concentration between 0.1 and 20% by weight, preferably between 5 and 10% by weight.
  • Sodium hydroxide, sodium carbonate and potassium carbonate for example, can be selected as an alkaline agent, which is generally in a concentration between 0.1 and 20% by weight, preferably between 5 and 10 wt .-%, is included and gives the solution a pH between 10 and 14.
  • the fiber material to be dyed according to the invention in the method according to the invention can be used in all processing states, such as yarn, flake, sliver and piece goods, such as woven and knitted fabrics.
  • Dyeing proofs that can be used according to the invention are, for example, the various pull-out dyeing processes, such as dyeing on the jigger or on the reel runner or dyeing from a long or short liquor, dyeing in jet dyeing machines or using a block-hot steam fixing method for pure modified ones Fiber materials containing hydroxy groups as well as the high-temperature exhaust process and thermal insulation process for polyester fibers or mixed fibers made of polyester fibers and modified fibers containing hydroxy groups.
  • a dyeing temperature in the range from 100 to 140 ° C., preferably 110 to 130 ° C., is sufficient for dyeing the modified fiber materials containing hydroxyl groups, such as the modified cotton fiber.
  • a dyeing temperature of above 120 ° C., preferably above 130 ° C., in particular from 170 to 210 ° C. is appropriate for dyeing the polyester fiber components when using an exhaust process.
  • Mixed fiber materials which can be used according to the invention are usually dyed above 180 ° C. when used by the thermal insulation process.
  • Dyeing proofs which can be used according to the invention are also the customary printing processes for the production of prints on textile fiber materials, including ink-jet printing and transfer printing.
  • the suitable temperature range for fixing the fiber-reactive disperse dye must be selected depending on the type of fiber used.
  • the fiber-reactive disperse dye which was applied to a mixed fabric of modified cellulose fiber and polyester fiber that can be used according to the invention, for example by the ink-jet technique, can be fixed on the fiber material after a short predrying phase using a thermal insulation method.
  • the dyeings of the modified hydroxyl-containing fiber materials obtainable in the manner according to the invention do not require any further aftertreatment after removal from the dyebath or after the dye has been fixed on the substrate, in particular no complicated aftertreatment process, including washing. As a rule, it is sufficient to rinse the colored substrate one or more times warm or hot and optionally cold water, which can optionally contain a nonionic wetting agent. A final boiling treatment of the dyed substrate with a washing solution to improve the fastness properties is not necessary.
  • Fiber-reactive disperse dyes which can be used according to the invention in the dyeing process according to the invention are dyes which, apart from the fiber-reactive group, contain no water-solubilizing group, the fiber-reactive group itself not being or possessing a water-solubilizing group or having only such a water-solubilizing group which is split off under the dyeing conditions, such as, for example, the ⁇ -sulfatoethylsulfonyl group, which is capable of transitioning into the vinylsulfonyl group at temperatures above 100.degree.
  • Fiber-reactive groups are generally understood to mean those parts of the molecule which contain hydroxyl groups of the fiber materials, such as, for example, cellulose or the amino and thiol groups of fiber materials, such as, for example, wool and silk, or of synthetic polymers, such as polyamides, or the amino groups of those with amino compounds modified hydroxy group-containing fiber materials and can form a covalent chemical bond with these groups.
  • Particularly interesting fiber-reactive radicals are fluorine and chloro-1,3,5-triazine radicals of the formula (4) in which Hal is chlorine or fluorine and Q is an amino, alkylamino, N, N-dialkylamino, cycloalkylamino, N, N-dicycloalkylamino, aralkylamino, arylamino, N-alkyl-N-cyclohexylamino, N-alkyl -N-arylamino group or an amino group which contains a heterocyclic radical which may have a further fused-on carbocyclic ring, or amino groups in which the amino nitrogen atom is a member of an N-heterocyclic ring which optionally contains further heteroatoms, and hydrazino and semicarbazido groups, where the alkyl radicals mentioned can be straight-chain or branched and low molecular weight and higher molecular weight, preferably those having 1 to 6 carbon atoms.
  • Suitable cycloalkyl, aralkyl and aryl radicals are, in particular, cyclohexyl, benzyl, phenethyl, phenyl and naphthyl radicals; Heterocyclic residues are especially furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzothiazole and benzoxazole residues.
  • Suitable amino groups, in which the amino nitrogen atom is a member of an N-heterocyclic ring are preferably residues of six-membered N-heterocyclic compounds which may contain nitrogen, oxygen or sulfur as further heteroatoms.
  • alkyl, cycloalkyl, aralkyl and aryl radicals, the heterocyclic radicals and the N-heterocyclic rings can additionally be substituted, for example by halogen, such as fluorine, chlorine and bromine, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C1 -C4 alkyl, C1-C4 alkoxy, acylamino groups such as acetylamino or benzoylamino, or ureido.
  • halogen such as fluorine, chlorine and bromine
  • sulfamoyl carbamoyl
  • C1 -C4 alkyl C1-C4 alkoxy
  • acylamino groups such as acetylamino or benzoylamino, or ureido.
  • amino groups are: -NH2, methylamino, ethylamino, propylamino, isopropylamino, butylamino, hexylamino, ⁇ -methoxyethylamino, ⁇ -methoxypropylamino, ⁇ -ethoxyethylamino, N, N-dimethylamino, N, N-diethylamino, ⁇ -chloroethylamino , ⁇ -cyanoethylamino, ⁇ -cyanopropylamino, benzylamino, phenethylamino, cyclohexylamino, phenylamino, toluidino, xylidino, chloranilino, anisidino, phenetidino, N-methyl-N-phenylamino, N-ethyl-N-phenylamino, morpholino, piperidino Semicarbazi
  • Q can be an amino radical of the general formula -NR10R11, in which R10 is hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl or ethyl, and R11 is phenyl which is formed by a fiber-reactive radical of the vinylsulfone series directly or via a methylamino , Ethylamino-, methylene, ethylene or propylene group is substituted and which can still be substituted by 1 or 2 substituents from the group methoxy, ethoxy, methyl, ethyl and chlorine, or R11 is alkyl of 2 to 4 carbon atoms, such as Ethyl or n-propyl, which is substituted by a fiber-reactive group of the vinyl sulfone series, or alkylene phenyl with an alkylene radical of 1 to 4 carbon atoms, the phenyl of which is substituted by a fiber-reactive radical of the vinyl sulfone series, or in which R10
  • Such fiber-reactive disperse dyes are described, for example, in US Pat. Nos. 3,974,160, 3,959,338, 4,025,646, 4,473,499, 4,500,455, 4,515,716 and 4,837,390, in Swiss Patent No. 564,515 and in Japanese Patent Application Publication Hei-3-247 665.
  • the information in these patent official documents relating to these fiber-reactive disperse dyes is intended to be part of the disclosure of the present application.
  • aqueous pretreatment liquor which contains 750 parts of N- (2-sulfatoethyl) piperazine and 450 parts of sodium hydroxide.
  • the fleet is heated to 130 ° C with continuous goods guidance in the apparatus.
  • the liquor is left at this temperature for 30 minutes, then cooled to 80 ° C. and the cotton material is washed first with cold water, then with warm water at 60 ° C., a commercially available wetting agent being used, and again thoroughly with cold water to.
  • the pretreated but still wet product is mixed with 20,000 parts of water in the same machine.
  • 10 parts of a polyester / cotton blend fabric are in a liquor ratio of 1:10 with a liquor containing 50 parts of N- (2-sulfatoethyl) piperazine and 20 parts of sodium hydroxide per 1000 parts of water for 15 min pretreated at 95 ° C.
  • This process is followed by a washing process, first with cold, then with 60 ° C hot Water, which may contain a commercially available nonionic surfactant. After washing again with cold water, the fabric pretreated in this way is fed directly into a single-bath dyeing process.
  • 30 parts of bleached cotton yarn are exposed on a package in a yarn dyeing apparatus in 450 parts of a pretreatment liquor consisting of 50 parts of N- (2-sulfatoethyl) piperazine, 30 parts of sodium hydroxide and 1000 parts of water, by heating the liquor heated to 130 ° C alternately pumps from the inside to the outside and from the outside to the inside through the coil. After 30 minutes, the liquor is cooled, the dyed material is rinsed thoroughly with cold water and then washed at 60 ° C. for about 5 minutes, a nonionic surfactant being able to be used. After a new rinse cycle, the yarn is directly subjected to a dyeing process.
  • a pretreatment liquor consisting of 50 parts of N- (2-sulfatoethyl) piperazine, 30 parts of sodium hydroxide and 1000 parts of water
  • the dyeing machine is filled with 450 parts of an aqueous liquor, which contains 0.6 part of the fiber-reactive disperse dye known from Example 102 of German Offenlegungsschrift 2 008 811, and the liquor is heated to 120 ° C., the liquor being led applied in the pretreatment process. After 30 minutes at 120 ° C., the cooled liquor is removed and the colored material is rinsed and washed in the usual way. You get a yellow colored yarn with good fastness properties.
  • 10 parts of a polyester / cotton blend are with an aqueous liquor containing 50 parts of N- (2-sulfatoethyl) piperazine and 30 parts of sodium hydroxide per 1000 parts of water, with a liquor absorption of 80%, based on the weight of the fabric , padded and then subjected to heat setting at 180 ° C for 45 seconds.
  • the material is then rinsed cold and hot washed at 60 ° C for 10 minutes, using a non-ionic wetting agent.
  • the material After rinsing again with cold water, the material is transferred to an HT dyeing machine and treated at a liquor ratio of 1:20 with an aqueous liquor which contains 0.15 part of the fiber-reactive disperse dye known from Example 109 of German Offenlegungsschrift 2 008 811 .
  • the fiber mixture is dyed at 130 ° C. for 30 minutes.
  • the dyeing obtained is aftertreated by rinsing and soaping in the customary manner. A blue color is obtained on both fiber fractions with the very good fastness properties customary according to the prior art.
  • the procedure is, for example, analogous to that of Examples 1 to 4 above, but using one of the fiber-reactive dyes specified in the table examples below.
  • a strongly colored dyeing is obtained in the shade specified for the respective dye for both fiber components in a uniform shade and good fastness properties.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
EP94112297A 1993-08-13 1994-08-05 Procédé et utilisation de colorants réactifs de dispersion pour teindre ou imprimer des textiles en coton ou en mélange coton/polyester Withdrawn EP0638686A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4327301A DE4327301A1 (de) 1993-08-13 1993-08-13 Verfahren und Verwendung reaktiver Dispersionsfarbstoffe zum Färben oder Bedrucken aminierter, textiler Baumwoll- und Baumwoll-/Polyester-Mischgewebe
DE4327301 1993-08-13

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EP0638686A1 true EP0638686A1 (fr) 1995-02-15

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EP94112297A Withdrawn EP0638686A1 (fr) 1993-08-13 1994-08-05 Procédé et utilisation de colorants réactifs de dispersion pour teindre ou imprimer des textiles en coton ou en mélange coton/polyester

Country Status (6)

Country Link
US (1) US5498267A (fr)
EP (1) EP0638686A1 (fr)
JP (1) JPH07145574A (fr)
BR (1) BR9403236A (fr)
DE (1) DE4327301A1 (fr)
TW (1) TW290604B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0690166A3 (fr) * 1994-06-29 1996-05-01 Hoechst Ag Procédé pour teindu des tissus en mélanges cellulose aminée polyester avec des colorants dispersés réactifs
WO2004081279A1 (fr) * 2003-03-13 2004-09-23 Lenzing Aktiengesellschaft Procede pour colorer un melange constitue d'au moins deux types de fibres differents

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6623532B2 (en) * 2000-09-06 2003-09-23 Seiren Co., Ltd. Ink-jet printing method and printed goods
JP2012082546A (ja) * 2010-10-08 2012-04-26 Mimaki Engineering Co Ltd 分散染料(昇華型)によるインクジェット捺染に供される布帛の前処理剤及びその利用
ECSP11011300A (es) * 2011-09-02 2012-07-31 King Ernesto Quintana Compuesto químico especial único formulado para cambiar, mejorar y optimizar los procesos comunmente utilizados en la industria textil
US9844949B2 (en) 2013-02-12 2017-12-19 Sensient Colors Llc Ink compositions
CN110359299B (zh) * 2019-08-23 2022-01-11 浙江七色彩虹印染有限公司 一种涤纶低温染色携染剂及其制备方法和应用

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BE638513A (fr) *
BE635252A (fr) *
GB479341A (en) * 1936-06-03 1938-02-03 British Celanese Improvements in the treatment of filaments, threads, fabrics, films, and like materials
FR2226504A1 (fr) * 1973-04-19 1974-11-15 Ciba Geigy Ag
EP0009199A1 (fr) * 1978-09-22 1980-04-02 Hoechst Aktiengesellschaft Procédé de prétraitement de fibres cellulosiques, qui seront imprimées selon le procédé d'impression par transfert
EP0546476A1 (fr) * 1991-12-07 1993-06-16 Hoechst Aktiengesellschaft Procédé de préparation d'un matériau fibreux modifié et procédé de teinture du matériau fibreux modifié avec des colorants anioniques

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JPS55152875A (en) * 1979-05-14 1980-11-28 Mitsubishi Chem Ind Anthraquinone dyestuff for cellulose containing fibers
US4676803A (en) * 1979-07-07 1987-06-30 Bayer Aktiengesellschaft Reactive azo dyestuffs, free from anionic groups and containing a basic group and halogenotriazinyl radical and useful for dyeing cellulose/polyester
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BE638513A (fr) *
BE635252A (fr) *
GB479341A (en) * 1936-06-03 1938-02-03 British Celanese Improvements in the treatment of filaments, threads, fabrics, films, and like materials
FR2226504A1 (fr) * 1973-04-19 1974-11-15 Ciba Geigy Ag
EP0009199A1 (fr) * 1978-09-22 1980-04-02 Hoechst Aktiengesellschaft Procédé de prétraitement de fibres cellulosiques, qui seront imprimées selon le procédé d'impression par transfert
EP0546476A1 (fr) * 1991-12-07 1993-06-16 Hoechst Aktiengesellschaft Procédé de préparation d'un matériau fibreux modifié et procédé de teinture du matériau fibreux modifié avec des colorants anioniques

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0690166A3 (fr) * 1994-06-29 1996-05-01 Hoechst Ag Procédé pour teindu des tissus en mélanges cellulose aminée polyester avec des colorants dispersés réactifs
US5578088A (en) * 1994-06-29 1996-11-26 Hoechst Aktiengesellschaft Process for dyeing aminated cellulose/polyester blend fabric with fiber-reactive disperse dyestuffs
WO2004081279A1 (fr) * 2003-03-13 2004-09-23 Lenzing Aktiengesellschaft Procede pour colorer un melange constitue d'au moins deux types de fibres differents

Also Published As

Publication number Publication date
JPH07145574A (ja) 1995-06-06
TW290604B (fr) 1996-11-11
BR9403236A (pt) 1995-04-11
DE4327301A1 (de) 1995-02-16
US5498267A (en) 1996-03-12

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