EP1664420A2 - Process for printing or dyeing cellulose/polyester mixed fibres - Google Patents

Process for printing or dyeing cellulose/polyester mixed fibres

Info

Publication number
EP1664420A2
EP1664420A2 EP04766635A EP04766635A EP1664420A2 EP 1664420 A2 EP1664420 A2 EP 1664420A2 EP 04766635 A EP04766635 A EP 04766635A EP 04766635 A EP04766635 A EP 04766635A EP 1664420 A2 EP1664420 A2 EP 1664420A2
Authority
EP
European Patent Office
Prior art keywords
hydrogen
denotes
formula
process according
alkyl
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.)
Withdrawn
Application number
EP04766635A
Other languages
German (de)
English (en)
French (fr)
Inventor
Véronique Hall-Goulle
Athanassios Tzikas
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.)
Huntsman Advanced Materials Switzerland GmbH
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC 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 Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Priority to EP04766635A priority Critical patent/EP1664420A2/en
Publication of EP1664420A2 publication Critical patent/EP1664420A2/en
Withdrawn legal-status Critical Current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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/36—Material containing ester groups using dispersed dyestuffs
    • 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
    • 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
    • D06P1/16—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 dispersed, e.g. acetate, dyestuffs
    • 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
    • D06P1/60—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 polyethers
    • D06P1/613—Polyethers without nitrogen
    • 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
    • D06P1/60—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 polyethers
    • D06P1/613—Polyethers without nitrogen
    • D06P1/6138—Polymerisation products of glycols, e.g. Carbowax, Pluronics
    • 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
    • D06P1/90—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 dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/908—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 dyes dissolved in organic solvents or aqueous emulsions thereof using specified 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
    • D06P3/82—Textiles which contain different kinds of fibres
    • 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
    • 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

Definitions

  • the invention relates to a process for printing or dyeing water swellable cellulose fibres or cellulose/polyester mixed fibres with specific disperse dyes.
  • DE 1 811 796 describes a process for dyeing cellulose fibres or blends of cellulose fibres and synthetic fibres with a single disperse dye which process comprises contacting said cellulosic material with water in sufficient amount to swell the cellulose, a solution or dispersion of the dye and a high-boiling water-soluble solvent in an amount sufficient to maintain swelling of the cellulose if water is removed.
  • the present invention relates to a process for printing or dyeing cellulose fibres or cellulose/polyester mixed fibres characterised in that the fibres are treated in any sequence with water, a water-soluble organic solvent having a boiling point >150 °C and a disperse dye selected from the compounds of formulae (1) to (10)
  • Ri and R 2 are each independently of the other C ⁇ -C 8 -alkyl, -(CH 2 ) n -O-(CH2) m R 5 , wherein R 5 denotes hydrogen or C ⁇ -C 8 -alkyl, n is a number from 2 to 6 and m is a number from 0 to 6, Cs-C ⁇ aryl, which is unsubstituted or substituted with one or more hydroxy groups, C C 8 alkyl groups, CrC alkoxy groups or halogen atoms or C ⁇ -Csoaralkyl, which is unsubstituted or substituted with one or more hydroxy groups, C ⁇ -C alkyl groups, Cr
  • R 3 and R are each independently of the other chlorine, bromine, cyano, methyl or trifluoromethyl,
  • X is a radical of formula (1a), (1 b), (1c) or (1d)
  • R 6 and R 7 independently of the other represent hydrogen, chlorine, bromine or cyano
  • R 8 denotes CrC 8 -alkyl or -(CH 2 ) n -O-(CH 2 ) m R 5 ⁇ wherein R denotes hydrogen or C C 8 -alkyI, n is a number from 2 to 6 and m is a number from 0 to 6,
  • R 9 is hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl or-SO 2 CH 3 and
  • R 10 represents hydrogen, hydroxy or amino
  • Rn denotes a radical of formula (2a), (2b), (2c) or (2d) wherein R 17 is hydrogen, chlorine , bromine, methyl or methoxy,
  • R 18 is hydrogen, phenylamino, benzamido or CrC ⁇ 2 acyIamido, one of the radicals R ⁇ 2 , R 13 and R M denotes a radical of formula (2a), (2b), (2c) or (2d) as defined above and the others are hydrogen, and
  • R 15 and R ⁇ 6 are each independently of the other hydrogen, bromine or chlorine;
  • R 19 denotes C C 8 alkyl or -(CH 2 ) n -O-(CH 2 ) m -OR 2 o
  • R 20 is hydrogen, methyl or ethyl
  • n denotes a number from 2 to 6
  • m denotes a number from 0 to 6;
  • R 2 ⁇ is C C 8 alkyl, Cs-C 2 aryl, which is unsubstituted or substituted with one or more hydroxy groups, C C 8 alkyl groups, d-C 4 alkoxy groups or halogen atoms or C 6 -C 3 oaralkyl, which is unsubstituted or substituted with one or more hydroxy groups, C C alkyl groups,
  • R 22 and R 23 are each independently of the other hydrogen, bromine or chlorine;
  • R 24 denotes chlorine, bromine, cyano or-CONH 2 ,
  • R 25 is CrC 20 alkyl or -(CH 2 ) n -0-(CH 2 ) m R 5 , wherein R 5 denotes hydrogen or d-C ⁇ -alkyl, n is a number from 2 to 6 and m is a number from 0 to 6,
  • D is a radical of formula (1c) as defined above or a radical of formula (6a)
  • R 9 , R 10 and R 25 are as defined above;
  • R 26 denotes CrC 12 alkoxy
  • Me denotes Ni, Zn, Pd or preferably Cu
  • R 27 is hydrogen, d-C ⁇ alkoxy or -SO 2 -NH-R 25 and R 2 5 is as defined above; wherein R 28 and R 29 are each independently of the other a radical of formula (2b) or (2d) as defined above;
  • R 8 and R17 are as defined above.
  • the compounds of formulae (1) to (10) are known and either commercially available or can be prepared according to known processes.
  • Preferred compounds of formula (1) are those wherein R 3 is cyano and R 4 is methyl.
  • a compound of formula (1) is used as disperse dye, wherein R 3 is cyano, R 4 is methyl and X is a radical of formula (1a), (1b) or (1d).
  • Particularly preferred disperse dyes are the compounds of formula (1 ), wherein R 3 is cyano, R 4 is methyl and X is a radical of formula (1d).
  • Particularly preferred disperse dyes are the compounds of formulae (101), (102), (108), (109), (110), (115), (116), (118), (119), (120), (124), (133), (141), (143), (144), (152) and (154).
  • the most preferred disperse dyes are the compounds of formula (101) and (102)
  • the organic solvent used in the process according to the invention should be water-soluble and have a high dissolving capacity for the disperse dyes of formulae (1) to (10) at the fixation temperature.
  • Water-soluble in this context means solubility in water of at least 2.5 % by weight at 25 °C.
  • Suitable solvents of this type are glycols and their derivatives, in particular the ethers and esters.
  • the preferred organic solvents that can be applied in the process according to the invention are polyethylene glycol, polypropylene glycol or an ether or ester derivative of polyethylene glycol or polypropylene glycol.
  • Polyethylene glycol having a molecular weight of 100 to 600 is particularly preferred.
  • water, dye and solvent can be applied to the substrate in any sequence.
  • the preferred method for dyeing fabrics composed of cellulosic fibres or mixtures of cellulosic and synthetic fibres is to impregnate the fabric with a mixture of one or more dyes, water and solvent in a conventional dye pad bath followed by squeezing to remove excess dye liquor, or to print with a solvent-containing printing paste, and subsequently heating to evaporate sufficient water to effect dissolution of the dye, at which time the fabric is dyed.
  • water is evaporated, but in an insufficient amount to effect dissolution of the dye, after which pressure and heat are applied to effect dissolution without further evaporation of water.
  • Dye pastes can be prepared by conventional techniques such as by milling the dye in the presence of a dispersing agent or surfactant.
  • a dyebath can be prepared by diluting the dye paste with water or with aqueous solvent. Addition of a solvent to the dye paste before addition of water may cause dye separation and usually is avoided. It will be understood by those skilled in the art that conventional additives other than a dye solvent and a dispersing agent can be present in dye baths and printing pastes.
  • Further components which may be present in the printing pastes or dye baths are e.g. natural or synthetic thickeners, pigments, acids, bases and/or salts to adjust the pH to the desired value, anionic, nonionic or cationic surfactants, antifoaming and antifrosting agents, dispersing agents, fixing agents, polyhydroxy compounds, reaction products of hydroxyl compounds and isocyanates, polyesters prepared by reaction of terephthalic acid and one or more polyethylene glycols. These components are commonly used or recommended for textile printing or finishing.
  • the three components are preferably contemporaneously applied to the fibre.
  • the relative amounts of water, solvent and dye that can be applied in the printing pastes and dye baths are known to the skilled artisan.
  • the printing paste which can be applied in the process according to the invention preferably contains 50 to 95 %, more preferably 60 to 90 % and in particular 70 to 85 by weight of water, based on the total weight of the printing paste.
  • the amount of organic solvent is preferably 1 to 20 %, more preferably 2 to 15 % and in particular 5 to 10 by weight of, based on the total weight of the printing paste.
  • the amount of dye dispersion is preferably 1 to 15 %, more preferably 2 to 10 % and in particular 3 to 8 by weight of, based on the total weight of the printing paste.
  • the temperature at which dyeing or printing is effected by the instant process depends on the solubility of the dye in the dye solvent or aqueous dye solvent.
  • the fibres are heated in a liquor at 125 °C to 225 °C, said liquor containing as liquid ingredients 10 to 95 % by weight of water and 5 to 90 % by weight of organic solvent.
  • the cellulosic materials which can be dyed by the process of this invention include all forms of cellulose which increase in size and flexibility upon exposure to water. Suitable materials include natural fibres and purified wood pulps as well as reconstituted cellulose in fiber and film form.
  • the invention is particularly useful for dyeing cotton/polyester mixed fibres.
  • Each dye is dispersed according to the following formulation: • 29,2% dye • 7.3% 1,2-propylenglykol (solvent) • 3.7% Lutensol AT25 (dispersant) • 0.8% Geropon T77 (wetting agent) • 0.1 % Surfinol DF58 (antifoam agent) • 0.4% Proxel GXL (antimicrobial) • 58.5% deionised water
  • Zirconium beads (diameter 0.6 to 1 mm) are then added to the above-obtained dispersion in a glass bottle tightly closed. The bottle is then placed in a Scandex apparatus and thereby agitated for 4 hours.
  • the thus obtained fine dispersion is then filtered on a conventional Buchner funnel to provide the final dye dispersion.
  • Printing paste A typical run consists in the preparation of a mother paste, to which a quantity of the dye dispersion and water will be subsequently added.
  • the amount of added deionised water can vary as a function of the viscosity of the dye dispersion and/or of the printing paste.
  • the printing paste is applied in a classical way on the textile (CO or PES/CO) through a screen. After drying at 90°C, the textile is thermofixed at 220°C for 1 minute.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
EP04766635A 2003-09-08 2004-08-30 Process for printing or dyeing cellulose/polyester mixed fibres Withdrawn EP1664420A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP04766635A EP1664420A2 (en) 2003-09-08 2004-08-30 Process for printing or dyeing cellulose/polyester mixed fibres

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP03405656 2003-09-08
EP04766635A EP1664420A2 (en) 2003-09-08 2004-08-30 Process for printing or dyeing cellulose/polyester mixed fibres
PCT/EP2004/051952 WO2005024123A2 (en) 2003-09-08 2004-08-30 Process for printing or dyeing cellulose/polyester mixed fibres

Publications (1)

Publication Number Publication Date
EP1664420A2 true EP1664420A2 (en) 2006-06-07

Family

ID=34259308

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04766635A Withdrawn EP1664420A2 (en) 2003-09-08 2004-08-30 Process for printing or dyeing cellulose/polyester mixed fibres

Country Status (6)

Country Link
US (1) US20070000076A1 (ko)
EP (1) EP1664420A2 (ko)
KR (1) KR20060090805A (ko)
CN (1) CN1846028A (ko)
TW (1) TW200523428A (ko)
WO (1) WO2005024123A2 (ko)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007017430A1 (en) * 2005-08-11 2007-02-15 Huntsman Advanced Materials (Switzerland) Gmbh Infrared ray-absorbing fibers
US8399161B2 (en) 2007-02-23 2013-03-19 Basf Se Transparent colourants and colourant compositions, and their use
KR101231051B1 (ko) * 2010-11-29 2013-02-07 주식회사에스케이니트 레이온-폴리에스테르 교직물의 날염방법
KR101231050B1 (ko) * 2010-11-29 2013-02-07 주식회사에스케이니트 레이온-폴리에스테르 교직물의 염색방법
TWI707002B (zh) * 2016-05-25 2020-10-11 瑞士商杭斯曼高級材料公司 分散偶氮染料、其製備方法及其用途
PT3574055T (pt) 2017-01-27 2023-04-13 Huntsman Textile Effects Switzerland Gmbh Método para impressão de materiais de fibra têxtil de acordo com o processo de impressão a jato de tinta
JP2020515728A (ja) 2017-03-29 2020-05-28 ハンツマン アドバンスト マテリアルズ （スイッツァランド） ゲーエムベーハーＨｕｎｔｓｍａｎ Ａｄｖａｎｃｅｄ Ｍａｔｅｒｉａｌｓ （Ｓｗｉｔｚｅｒｌａｎｄ） Ｇｍｂｈ セルロースを含む紡織繊維材料の捺染方法
MX2019011959A (es) 2017-04-07 2019-11-07 Huntsman Adv Mat Switzerland Mezclas de colorante.
AU2018289505B2 (en) 2017-06-22 2022-02-10 Cotton Incorporated Fabric treatment compositions and methods

Family Cites Families (6)

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Publication number Priority date Publication date Assignee Title
DE1811796C3 (de) * 1968-11-25 1974-01-03 E.I. Du Pont De Nemours And Co., Wilmington, Del. (V.St.A.) Verfahren zum Färben von Cellulosefasern oder Gemischen derselben mit synthetischen Fasern
US3706525A (en) * 1971-03-08 1972-12-19 Du Pont Water swollen cellulose dyeing with high molecular weight disperse dye in a glycol ether solution
US3744967A (en) * 1971-03-22 1973-07-10 Du Pont Process for dyeing napped fabrics of water swellable cellulose fibers
DE2528743C2 (de) * 1975-06-27 1982-06-09 Basf Ag, 6700 Ludwigshafen Verfahren zum Färben und Bedrucken von Cellulose-Fasern oder Gemischen von Cellulose-Fasern mit synthetischen Fasern
AT373930B (de) * 1975-10-29 1984-03-12 Basf Ag Farbstoffzubereitungen fuer das faerben und bedrucken von cellulose und cellulosehaltigem textilmaterial
DE4432833A1 (de) * 1994-09-15 1996-03-21 Basf Ag Verfahren zum Färben von Melamin-Formaldehyd-Kondensationsprodukten

Non-Patent Citations (1)

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Title
See references of WO2005024123A2 *

Also Published As

Publication number Publication date
WO2005024123A3 (en) 2005-06-02
US20070000076A1 (en) 2007-01-04
TW200523428A (en) 2005-07-16
CN1846028A (zh) 2006-10-11
KR20060090805A (ko) 2006-08-16
WO2005024123A2 (en) 2005-03-17

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