EP0610156A1 - Procédé de teinture ou d'impression de matériaux textiles cellulosiques - Google Patents

Procédé de teinture ou d'impression de matériaux textiles cellulosiques Download PDF

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Publication number
EP0610156A1
EP0610156A1 EP94810046A EP94810046A EP0610156A1 EP 0610156 A1 EP0610156 A1 EP 0610156A1 EP 94810046 A EP94810046 A EP 94810046A EP 94810046 A EP94810046 A EP 94810046A EP 0610156 A1 EP0610156 A1 EP 0610156A1
Authority
EP
European Patent Office
Prior art keywords
alkaline earth
earth metal
metal salts
per liter
aqueous solution
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP94810046A
Other languages
German (de)
English (en)
Other versions
EP0610156B1 (fr
Inventor
Wolfgang Sütterlin
Rolf Bitterli
Paul Schafflützel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
Ciba Spezialitaetenchemie Holding AG
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 Geigy AG, Ciba Spezialitaetenchemie Holding AG filed Critical Ciba Geigy AG
Publication of EP0610156A1 publication Critical patent/EP0610156A1/fr
Application granted granted Critical
Publication of EP0610156B1 publication Critical patent/EP0610156B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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
    • 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
    • D06P1/673—Inorganic compounds
    • D06P1/67333—Salts or hydroxides
    • D06P1/6735—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
    • D06P1/67358—Halides or oxyhalides
    • 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
    • D06P1/38—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 reactive dyes
    • D06P1/382—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 reactive dyes reactive group directly attached to heterocyclic group
    • 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
    • D06P3/66—Natural or regenerated cellulose using reactive dyes
    • D06P3/663—Natural or regenerated cellulose using reactive dyes reactive group directly attached to heterocyclic group
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/921—Cellulose ester or ether

Definitions

  • the present invention relates to a novel process for dyeing or printing cellulose-containing fiber materials with chlorine-containing reactive dyes, in which the dyeings or prints obtained are washed with an aqueous solution to which alkaline earth metal salts have been added.
  • the present invention thus relates to a process for dyeing or printing cellulose-containing fiber materials with reactive dyes, which is characterized in that the fiber material is dyed or printed with at least one reactive dye containing a chlorotriazine residue and with an aqueous solution, to which an amount of at least 0 , 01 grams per liter of alkaline earth salts was added, washes.
  • the reactive dyes are derived in particular from the remainder of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl , Naphthoquinone, pyrenchinone or perylene tetracarbimide dye, preferably the rest of a monoazo, disazo, metal complex azo, anthraquinone or phthalocyanine dye.
  • the reactive dyes can contain, as further substituents, the substituents customary in organic dyes.
  • alkyl groups with 1 to 4 carbon atoms such as methyl, ethyl, propyl, isopropyl or butyl
  • alkoxy groups with 1 to 4 carbon atoms such as methoxy, ethoxy, propoxy, isopropoxy or butoxy
  • acylamino groups with 1 up to 8 carbon atoms especially alkanoylamino groups and alkoxycarbonylamino groups, such as acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino or benzoylamino, phenylamino, NN-di- ⁇ -hydroxyethylamino, N, N-di- ⁇ -sulfatoethylamino, sulfobenzylamino, N, N, N Alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy radical, such as methoxycarbonyl or
  • the phenyl radicals mentioned can, for example, be further substituted by C1-C Alkyl-alkyl, C1-C4-alkoxy, halogen or sulfo.
  • the reactive dyes preferably contain one or more sulfonic acid groups.
  • Preferred substituents are C1-C4-alkyl, C1-C4-alkoxy, halogen, amino, hydroxy, ureido, methylsulfonyl, sulfo, phenyl, phenylamino, sulfamoyl, N-alkylsulfamoyl with 1 to 4 carbon atoms and N-phenylsulfamoyl, where the phenyl radicals mentioned can be further substituted, for example by C1-C4-alkyl, C1-C4-alkoxy, halogen or sulfo.
  • Preferred chlorotriazine residues are those of the formula in which R2 and R3 are independently hydrogen or C1-C4 alkyl and T1 is hydrogen; phenyl optionally substituted by C1-C4 alkyl, halogen or sulfo, especially by sulfo; or C1-C6-alkyl, which may optionally be interrupted by a radical -O- and may optionally be further substituted by hydroxyl.
  • Another possible substituent for the phenyl radical mentioned is 1-amino-2-sulfo-anthraquinone- (4) -yl.
  • T1 is preferably hydrogen; phenyl optionally substituted by sulfo; C1-C6 alkyl; a radical of the formula -CH2CH2OCH2CH2OH; or 1-amino-2-sulfo-anthraquinone- (4) -yl.
  • T1 is particularly preferably hydrogen; phenyl optionally substituted by sulfo; or a radical of the formula -CH2CH2OCH2CH2OH.
  • Magnesium, calcium or barium salts, in particular magnesium or calcium salts, are preferably used as alkaline earth metal salts. Mixtures of alkaline earth salts can also be used, e.g. Mixtures of magnesium and calcium salts. Common salts such as e.g. the corresponding halides, e.g. Fluorine, bromine or especially chlorine, sulfates or oxides into consideration.
  • An addition of alkaline earth metal salts of 0.01 to 1 gram per liter, in particular 0.01 to 0.2 gram per liter, preferably 0.05 to 0.2 gram per liter is particularly preferred.
  • the customary dyeing or printing processes can be used for the process according to the invention.
  • the dyeing liquors or printing pastes can contain other additives, for example wetting agents, anti-foaming agents, leveling agents or agents which influence the property of the textile material, such as e.g. Plasticizers, additives for flame retardants or dirt, water and oil repellents as well as water softening agents and natural or synthetic thickeners, e.g. Alginates and cellulose ethers.
  • the method for printing is preferred.
  • the printed fiber material is washed in a first washing process with water which does not has substantial content of alkaline earth metal salts, washed, and washed in a second washing process with an aqueous solution to which at least 0.01 grams per liter of alkaline earth metal salts were added.
  • An insignificant content of alkaline earth metal salts means a content of less than 0.01 grams per liter, in particular less than 0.005 grams per liter and preferably less than 0.001 grams per liter.
  • the printed fiber material is cold washed in a first washing process with water which has no substantial content of alkaline earth metal salts (for example at a temperature of 5 to 40 ° C.) and in a second washing process with a aqueous solution, to which at least 0.01 grams per liter of alkaline earth metal salts have been added, first washed hot (for example at a temperature of 80 to 110 ° C) and then cold (for example at a temperature of 5 to 40 ° C).
  • mixtures of two or more dyes can also be used as dyes.
  • At least one of the dyes of the formulas (6) to (8) is preferably used.
  • the dyes used in the process according to the invention are known or can be prepared by known processes.
  • cellulose-containing fiber materials are natural cellulose fibers such as cotton, linen and hemp, as well as cellulose and regenerated cellulose.
  • Cellulose-containing fiber materials which are contained in blended fabrics may also be mentioned, e.g. Mixtures of cotton with polyester fibers or polyamide fibers.
  • the dyeings and prints obtained by the process according to the invention have a high color strength and a high fiber-dye binding stability, furthermore good light fastness and very good wet fastness properties, such as fastness to washing, water, sea water, overdyeing and sweating, and good fastness to pleating , Ironing fastness and rubbing fastness.
  • a printing paste is made according to the following recipe:
  • This printing paste is used to print a cotton fabric in a conventional manner (flat film printing).
  • the printed cotton fabric is dried and steamed in saturated steam for 10 minutes at approx. 100 ° C.
  • the printed fabric is then washed cold with deionized water and then boiled, and then washed with an aqueous solution containing 0.09 g / l calcium chloride, cold, boiling and then cold again.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Coloring (AREA)
EP94810046A 1993-02-05 1994-01-27 Procédé de teinture ou d'impression de matériaux textiles cellulosiques Expired - Lifetime EP0610156B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH358/93 1993-02-05
CH35893 1993-02-05

Publications (2)

Publication Number Publication Date
EP0610156A1 true EP0610156A1 (fr) 1994-08-10
EP0610156B1 EP0610156B1 (fr) 1997-05-28

Family

ID=4185201

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94810046A Expired - Lifetime EP0610156B1 (fr) 1993-02-05 1994-01-27 Procédé de teinture ou d'impression de matériaux textiles cellulosiques

Country Status (4)

Country Link
US (1) US5403360A (fr)
EP (1) EP0610156B1 (fr)
JP (1) JPH06235176A (fr)
DE (1) DE59402856D1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005045125A1 (fr) * 2003-11-11 2005-05-19 Ciba Specialty Chemicals Holding Inc. Procede de teinture ou d'impression de materiaux a base de fibres textiles mettant en oeuvre des colorants reactifs

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5984979A (en) * 1997-10-08 1999-11-16 Sybron Chemicals Inc. Method of reactive dyeing of textile materials using carboxylate salt
MY162329A (en) 2004-03-19 2017-05-31 Ciba Specialty Chemicals Holding Inc Mixtures or reactive dyes and their use.
CN101565560B (zh) * 2009-04-14 2012-10-17 丽源(湖北)科技有限公司 一种红色活性染料混合物及其制备及使用
CN102808340B (zh) * 2012-08-21 2014-09-17 义乌市中力工贸有限公司 一种稳定的液体分散染色后还原清洗剂
EP3336148A1 (fr) * 2016-12-15 2018-06-20 DyStar Colours Distribution GmbH Mélanges de teintures bleues et marines réagissant aux fibres
CN108624083A (zh) * 2018-06-01 2018-10-09 东华大学 一类高耐光色牢度绿色活性染料及其制备方法和应用
CN108624084A (zh) * 2018-06-01 2018-10-09 东华大学 一类蒽醌系嫩绿色活性染料及其制备方法和应用
CN108504137B (zh) * 2018-06-01 2022-03-18 东华大学 一类基于间脲基苯胺系绿色活性染料及其制备方法和应用
CN110387143B (zh) * 2019-07-22 2020-12-15 浙江瑞华化工有限公司 一种黄色活性染料组合物及其制备方法和用途

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0044463A1 (fr) * 1980-07-17 1982-01-27 Bayer Ag Procédé de teinture et d'impression avec des colorants réactifs
SU927875A1 (ru) * 1980-10-13 1982-05-15 Ивановский Химико-Технологический Институт Способ крашени целлюлозных материалов

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4659333A (en) * 1984-09-28 1987-04-21 Ciba-Geigy Corporation Process for fixing dyes and prints with hot steam containing air
DE3671487D1 (de) * 1985-10-14 1990-06-28 Ciba Geigy Ag Verfahren zur nachbehandlung von mit sulfogruppenhaltigen farbstoffen gefaerbtem cellulosematerial.
EP0441745B1 (fr) * 1990-02-06 1995-07-12 Ciba SC Holding AG Procédé d'impression d'un matière textile cellulosique avec des colorants réactifs

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0044463A1 (fr) * 1980-07-17 1982-01-27 Bayer Ag Procédé de teinture et d'impression avec des colorants réactifs
SU927875A1 (ru) * 1980-10-13 1982-05-15 Ивановский Химико-Технологический Институт Способ крашени целлюлозных материалов

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 88, no. 10, 1978, Columbus, Ohio, US; abstract no. 137845r, TDA, KINJIRO ET AL.: "Dyeing of textiles" page 62; column 1; *
CHEMICAL ABSTRACTS, vol. 97, no. 16, 1982, Columbus, Ohio, US; abstract no. 129074j, KIRILLOVA ET AL.: "Dyeing of cellulose materials" page 79; column 2; *
G. GONGYI ET AL.: "New approach to modifying cotton for improved dyeability with reactive dyes", AMERICAN DYESTUFF REPORTER, vol. 81, no. 11, 1992, SECAUCUS, NJ, US, pages 180 - 186, XP000324889 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005045125A1 (fr) * 2003-11-11 2005-05-19 Ciba Specialty Chemicals Holding Inc. Procede de teinture ou d'impression de materiaux a base de fibres textiles mettant en oeuvre des colorants reactifs
US7553339B2 (en) 2003-11-11 2009-06-30 Huntsman International Llc Method of dyeing or printing textile fibre materials using reactive dyes

Also Published As

Publication number Publication date
DE59402856D1 (de) 1997-07-03
US5403360A (en) 1995-04-04
EP0610156B1 (fr) 1997-05-28
JPH06235176A (ja) 1994-08-23

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