WO2005024123A2 - Process for printing or dyeing cellulose/polyester mixed fibres - Google Patents

Process for printing or dyeing cellulose/polyester mixed fibres Download PDF

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Publication number
WO2005024123A2
WO2005024123A2 PCT/EP2004/051952 EP2004051952W WO2005024123A2 WO 2005024123 A2 WO2005024123 A2 WO 2005024123A2 EP 2004051952 W EP2004051952 W EP 2004051952W WO 2005024123 A2 WO2005024123 A2 WO 2005024123A2
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Prior art keywords
hydrogen
denotes
formula
process according
alkyl
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PCT/EP2004/051952
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French (fr)
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WO2005024123A3 (en
Inventor
Véronique Hall-Goulle
Athanassios Tzikas
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Ciba Specialty Chemicals Holding Inc.
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Priority to EP04766635A priority Critical patent/EP1664420A2/en
Priority to US10/570,473 priority patent/US20070000076A1/en
Publication of WO2005024123A2 publication Critical patent/WO2005024123A2/en
Publication of WO2005024123A3 publication Critical patent/WO2005024123A3/en

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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—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
    • 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
    • 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.

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

Abstract

The 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 watersoluble organic solvent having a boiling point >150 °C and a specific disperse dye.

Description

Process for Printing or Dyeing Cellulose or Cellulose/Polyester Mixed Fibres
The invention relates to a process for printing or dyeing water swellable cellulose fibres or cellulose/polyester mixed fibres with specific disperse dyes.
Many attempts have been made to develop efficient processes for printing or dyeing polyester-cotton blends.
Two fundamentally different approaches were taken:
Processes using one class of dye only and processes using mixtures of two classes of dyes. Usually reactive dyes or vat dyes are combined with disperse dyes. However, the use of such dye mixtures is associated with several drawbacks and it is hardly possible to obtain the same colour and depth on the two fibres by this method.
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.
In J. Soc. Dyers Colour., 96, 347-354 (1980) specific disperse dyes (Cellestren®, supplied by BASF) in combination with Glyezin® CD, a polyalkylene oxide derivative, are recommended for application in the printing process described in DE 1 811 796. The prints on polyester- cotton blends obtained by this process are described as exhibiting brilliant colours with the same depth of colour on both fibres.
However, the Cellestren/Glyezin system does not meet the top requirements with respect to light fastness and wash fastness.
It has now been found that the application of some specific disperse dyes in the process disclosed in DE 1 811 796 yields prints and dyeings on polyester-cotton blends having extraordinarily good light fastness and wash fastness.
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)
Figure imgf000003_0001
wherein Ri and R2 are each independently of the other Cι-C8-alkyl, -(CH2)n-O-(CH2)mR5, wherein R5 denotes hydrogen or Cι-C8-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 C8alkyl groups, CrC alkoxy groups or halogen atoms or Cβ-Csoaralkyl, which is unsubstituted or substituted with one or more hydroxy groups, Cι-C alkyl groups, Cr
C4alkoxy groups or halogen atoms,
R3 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)
Figure imgf000003_0002
wherein R6 and R7 independently of the other represent hydrogen, chlorine, bromine or cyano,
R8 denotes CrC8-alkyl or -(CH2)n-O-(CH2)mR5ι wherein R denotes hydrogen or C C8-alkyI, n is a number from 2 to 6 and m is a number from 0 to 6,
R9 is hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl or-SO2CH3 and
R10 represents hydrogen, hydroxy or amino;
Figure imgf000003_0003
wherein Rn denotes a radical of formula (2a), (2b), (2c) or (2d)
Figure imgf000004_0001
wherein R17 is hydrogen, chlorine , bromine, methyl or methoxy,
R18 is hydrogen, phenylamino, benzamido or CrCι2acyIamido, one of the radicals Rι2, R13 and RM denotes a radical of formula (2a), (2b), (2c) or (2d) as defined above and the others are hydrogen, and
R15 and Rι6 are each independently of the other hydrogen, bromine or chlorine;
Figure imgf000004_0002
wherein R19 denotes C C8alkyl or -(CH2)n-O-(CH2)m-OR2o, and R20 is hydrogen, methyl or ethyl, n denotes a number from 2 to 6 and m denotes a number from 0 to 6;
Figure imgf000004_0003
wherein R2ι is C C8alkyl, Cs-C2 aryl, which is unsubstituted or substituted with one or more hydroxy groups, C C8alkyl groups, d-C4alkoxy groups or halogen atoms or C6-C3oaralkyl, which is unsubstituted or substituted with one or more hydroxy groups, C C alkyl groups,
CrC alkoxy groups or halogen atoms;
Figure imgf000004_0004
wherein R22 and R23 are each independently of the other hydrogen, bromine or chlorine;
Figure imgf000005_0001
wherein R24 denotes chlorine, bromine, cyano or-CONH2,
R25 is CrC20alkyl or -(CH2)n-0-(CH2)mR5, wherein R5 denotes hydrogen or d-Cβ-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)
Figure imgf000005_0002
wherein R9, R10 and R25 are as defined above;
Figure imgf000005_0003
wherein R26 denotes CrC12alkoxy;
Figure imgf000005_0004
wherein Me denotes Ni, Zn, Pd or preferably Cu,
R27 is hydrogen, d-C^alkoxy or -SO2-NH-R25 and R25 is as defined above;
Figure imgf000006_0001
wherein R28 and R29 are each independently of the other a radical of formula (2b) or (2d) as defined above;
Figure imgf000006_0002
wherein R8 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 R3 is cyano and R4 is methyl.
In a preferred embodiment of the invention a compound of formula (1) is used as disperse dye, wherein R3 is cyano, R4 is methyl and X is a radical of formula (1a), (1b) or (1d).
Particularly preferred disperse dyes are the compounds of formula (1 ), wherein R3 is cyano, R4 is methyl and X is a radical of formula (1d).
Further preferred disperse dyes are the following compounds:
Figure imgf000006_0003
Figure imgf000007_0001
Figure imgf000008_0001
Figure imgf000009_0001
Figure imgf000010_0001
Figure imgf000011_0001
Figure imgf000012_0001
Figure imgf000013_0001
Figure imgf000014_0001
Figure imgf000015_0001
Figure imgf000016_0001
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)
All the embodiments described in DE 1 811 796, hereby incorporated by reference, can basically be performed by using the disperse dyes of formula (1) to (10).
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.
In dyeing cellulosic materials by the process of the invention, 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. Alternatively, 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.
Although it is possible to treat the fibres in any sequence with water, solvent and dye, 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.
Preferably, 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.
The following non-limitative Examples illustrate the invention in more detail. Application Examples:
1. Dispersion
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.
2. 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.
Mother paste: • 84.2% deionised water • 0.8% NH4OH (28%) • 0.4% Alcoprint PA-NS • 9.9% PEG400 • 2.3% Alcoprint PSC • 2.4% Alcoprint PTP
Printing paste • 33.3% deionised water • 60.1 % mother paste • 6.6% dye dispersion The amount of added deionised water can vary as a function of the viscosity of the dye dispersion and/or of the printing paste.
3. Printing
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.
After a brief cold rinse, a 30 minutes wash at 80°C is performed in a bath containing: • 2g/L carbonate • 1g/L Calgon • 1g/L UItravon JU
4. Tests All thus obtained printed fabrics exhibit a very good light fastness, wash fastness and wet rubbing fastness.

Claims

Claims
1. 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)
Figure imgf000021_0001
wherein R^ and R2 are each independently of the other Cι-C8-alkyl, -(CH2)n-0-(CH2)mR5, wherein R5 denotes hydrogen or CrC8-alkyl, n is a number from 2 to 6 and m is a number from 0 to 6, C5-C24aryl, which is unsubstituted or substituted with one or more hydroxy groups, C C8alkyl groups, C C4alkoxy groups or halogen atoms or Ce-Csoaralkyl, which is unsubstituted or substituted with one or more hydroxy groups, C C4alkyl groups, C C alkoxy groups or halogen atoms,
R3 and R4 are each independently of the other chlorine, bromine, cyano, methyl or trifluoromethyl,
X is a radical of formula (1a), (1b), (1c) or (1d)
Figure imgf000021_0002
wherein R6 and R7 independently of the other represent hydrogen, chlorine, bromine or cyano,
R8 denotes CrC8-alkyl or -(CH2)n-O-(CH2)mR5, wherein R5 denotes hydrogen or C C8-alkyl, n is a number from 2 to 6 and m is a number from 0 to 6, R9 is hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl or-SO2CH3 and
Rio represents hydrogen, hydroxy or amino;
Figure imgf000022_0001
wherein Rn denotes a radical of formula (2a), (2b), (2c) or (2d)
Figure imgf000022_0002
wherein R17 is hydrogen, chlorine , bromine, methyl or methoxy, Rι8 is hydrogen, phenylamino, benzamido or C C12acylamido, one of the radicals Rι2, R13 and RM denotes a radical of formula (2a), (2b), (2c) or (2d) as defined above and the others are hydrogen, and
R15 and Rι6 are each independently of the other hydrogen, bromine or chlorine;
Figure imgf000022_0003
wherein R19 denotes Cι-C8alkyl or -(CH2)n-O-(CH2)m-OR2o, and R2o is hydrogen, methyl or ethyl, n denotes a number from 2 to 6 and m denotes a number from 0 to 6;
Figure imgf000022_0004
wherein R2ι is CrC8alkyl, C5-C2 aryl, which is unsubstituted or substituted with one or more hydroxy groups, C C8alkyl groups, C C4alkoxy groups or halogen atoms or C6-C3oaralkyl, which is unsubstituted or substituted with one or more hydroxy groups, C C4alkyl groups, d-C alkoxy groups or halogen atoms;
Figure imgf000023_0001
wherein R22 and R23 are each independently of the other hydrogen, bromine or chlorine;
Figure imgf000023_0002
wherein R2 denotes chlorine, bromine, cyano or -CONH2,
R25 is Ci-C2oalkyl or -(CH2)n-0-(CH2)mR5, wherein R5 denotes hydrogen or Cι-C8-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)
Figure imgf000023_0003
wherein R9, R10 and R25 are as defined above;
Figure imgf000023_0004
wherein R26 denotes C C12alkoxy;
Figure imgf000024_0001
wherein Me denotes Cu, Ni, Zn or Pd,
R27 is hydrogen, d-C^alkoxy or -SO2-NH-R25 and R25 is as defined above;
Figure imgf000024_0002
wherein R28 and R29 are each independently of the other a radical of formula (2b) or (2d) as defined above;
Figure imgf000024_0003
wherein R8 and R17 are as defined above.
2. A process according to claim 1, characterised in that a compound of formula (1) is used as disperse dye, wherein R3 is cyano and R4 is methyl.
3. A process according to claim 2, characterised in that a compound of formula (1) is used as disperse dye, wherein X is a radical of formula (1a), (1b) or (1d).
4. A process according to claim 3, characterised in that the disperse dye is a compound of formula (101) or (102)
Figure imgf000025_0001
5. A process according to claim 1, characterised in that the organic solvent is polyethylene glycol, polypropylene glycol or an ether or ester derivative of polyethylene glycol or polypropylene glycol.
6. A process according to claim 5, characterised in that the organic solvent is polyethylene glycol having a molecular weight of 100 to 600.
7. A process according to claim 1 , characterised in that water, organic solvent and disperse dye are contemporaneously applied to the fibre.
8. A printing process according to claim 1, characterised in that the printing paste contains 50 to 95 % by weight of water, based on the total weight of the printing paste.
9. A printing process according to claim 1, characterised in that the printing paste contains 1 to 20 % by weight of organic solvent, based on the total weight of the printing paste.
10. A printing process according to claim 1, characterised in that the printing paste contains 1 to 15 % by weight of a dye dispersion, based on the total weight of the printing paste.
11. A dyeing process according to claim 1 , characterised in that 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.
12. A process according to claim 1, characterised in that the fibres are cotton/polyester mixed fibres.
PCT/EP2004/051952 2003-09-08 2004-08-30 Process for printing or dyeing cellulose/polyester mixed fibres WO2005024123A2 (en)

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US8399161B2 (en) 2007-02-23 2013-03-19 Basf Se Transparent colourants and colourant compositions, and their use
TWI707002B (en) * 2016-05-25 2020-10-11 瑞士商杭斯曼高級材料公司 Disperse azo dyes, a process for the preparation thereof and the use thereof
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