WO2012095284A1 - Disperse dye mixtures, their preparation and use - Google Patents

Disperse dye mixtures, their preparation and use Download PDF

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Publication number
WO2012095284A1
WO2012095284A1 PCT/EP2012/000049 EP2012000049W WO2012095284A1 WO 2012095284 A1 WO2012095284 A1 WO 2012095284A1 EP 2012000049 W EP2012000049 W EP 2012000049W WO 2012095284 A1 WO2012095284 A1 WO 2012095284A1
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WO
WIPO (PCT)
Prior art keywords
hydrogen
alkyl
formula
methyl
dye
Prior art date
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PCT/EP2012/000049
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English (en)
French (fr)
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WO2012095284A9 (en
Inventor
Markus Arnold
Adrian Murgatroyd
Clemens Grund
Gunter GÖRLITZ
Timo Liebig
Original Assignee
Dystar Colours Distribution Gmbh
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 Dystar Colours Distribution Gmbh filed Critical Dystar Colours Distribution Gmbh
Priority to US13/979,756 priority Critical patent/US9096972B2/en
Priority to CN201280003182.7A priority patent/CN103890103B/zh
Priority to MX2013005776A priority patent/MX2013005776A/es
Priority to BR112013017510-9A priority patent/BR112013017510B1/pt
Priority to CA2806856A priority patent/CA2806856C/en
Priority to JP2013548779A priority patent/JP5876508B2/ja
Priority to KR1020137017606A priority patent/KR101782194B1/ko
Priority to EP12701666.5A priority patent/EP2663600B1/en
Priority to ES12701666.5T priority patent/ES2652518T3/es
Publication of WO2012095284A1 publication Critical patent/WO2012095284A1/en
Publication of WO2012095284A9 publication Critical patent/WO2012095284A9/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • 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
    • D06P1/18—Azo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008—Preparations of disperse dyes or solvent dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008—Preparations of disperse dyes or solvent dyes
    • C09B67/0082—Preparations of disperse dyes or solvent dyes in liquid form
    • 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
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/30—Ink jet printing

Definitions

  • Disperse dye mixtures their preparation and use
  • the present invention relates to the field of disperse dyes for dyeing hydrophobic textile materials.
  • Disperse azo dyes in which the chromophore is linked to 2-oxoalkylketo groups are known and described for example in WO 2009/037215 A2, WO 2008/090042 A1 , WO 2008/049758 A2, WO2005/056690 A1 , as well as GB 909843 A and
  • WO 95/20014 A1 discloses a dyeing process wherein dye mixtures can be used.
  • Azo dyes with an -SO2F group are concerned, and they can be used as dye mixtures or in admixture with dyes without an -SO 2 F group.
  • Possible candidates mentioned include azo dyes in which the chromophore is linked to 2-oxoalkylketo groups.
  • the present invention provides dye mixtures containing at least one dye of formula (I)
  • R 3 is hydrogen, (d-C 6 )-alkyl, substituted (Ci-C 6 )-alkyl, (C 3 -C 4 )-alkenyl or substituted (C3-C 4 )-alkenyl, especially benzyl, butyl, 2-cyanoethyl or a moiety of formula -CHR 4 -CnH 2 n-CHR 6 -COO-CHR 7 -CO-R 5 , or R 2 and R 3 combine
  • R 4 is hydrogen, (CrC 6 )-alkyl or phenyl
  • R 5 is (CrC 6 )-alkyl or substituted (Ci-C 6 )-alkyl
  • R 6 is hydrogen or (Ci-C6)-alkyl
  • R 7 is hydrogen, (Ci-C6)-alkyl or phenyl
  • n 0, 1 , 2 or 3, and at least one dye of formula (II)
  • R 8 is hydrogen, (C C 6 )-alkyl, (Ci-C 4 )-alkoxy, hydroxyl, halogen, -NHCHO,
  • R 9 is hydrogen, halogen, (Ci-C 4 )-alkoxy, (CrC )-alkyl or aryloxy,
  • R 10 is hydrogen, (d-CeJ-alkyl, substituted (CrC 6 )-alkyl, (C 3 -C )-alkenyl or
  • R 12 , or R 9 and R 10 combine to form the moiety -C*H(CH 3 )CH 2 C(CH 3 ) 2 -, where the carbon atom marked * is attached to the phenyl nucleus,
  • R 1 1 is hydrogen, (Ci-Ce)-alkyl or phenyl
  • R 12 is hydrogen, (Ci-C 6 )-alkyl, substituted (C C 6 )-alkyl, (C 3 -C )-alkenyl or
  • X is -CO-0-, -0-CO-, -0-, -NH- or -S-,
  • o O or l
  • n 0, 1 , 2 or 3
  • D 1 and D 2 are the same or different and they each represent the residue of a diazo component, and/or at least one dye of formula (III)
  • R 13 is hydrogen, cyano or carboxamido
  • R 14 is methyl, ethyl or phenyl
  • R 15 is optionally substituted (CrC 6 )-alkyl or optionally substituted oxygen- interrupted (C 2 -C 6 )-alkyl, and
  • D 3 represents the residue of a diazo component.
  • Residues D 1 , D 2 and D 3 of a diazo component are more particularly the moieties customary in the field of disperse dyes and known to one skilled in the art.
  • D 1 , D 2 and D 3 each independently represent a group of formula (IVa)
  • T 1 and T 2 are each independently hydrogen, (CrC 6 )-alkyl, (Ci-C 4 )-alkoxy,
  • T 1 and T 2 combine to form the moiety -CONT 4 CO-,
  • T 14 hydrogen or (Ci-C 6 )-alkyl
  • T 3 and T 4 are each independently hydrogen, halogen, trifluoromethyl, cyano, -SCN, -SO2CH3 or nitro, provided at least one of T 1 , T 2 , T 3 and T 4 is not hydrogen; or represent a group of formula (IVb)
  • T 5 and T 5 are each independently hydrogen or halogen
  • T 6 is hydrogen, -SO 2 CH 3 , -SCN, (Ci-C 4 )-alkoxy, halogen or nitro, provided at least one of T 5 , T 5 ' and T 6 is not hydrogen; or represent a group of formula (IVc)
  • T 12 is hydrogen or halogen; or represent a group of formula
  • T 7 is nitro, -CHO, cyano, -COCH 3 or either a group of formula (IVda)
  • T 10 is hydrogen, halogen, nitro or cyano, or a group of formula (IVdb)
  • T 15 is (C C 6 )-alkyl
  • T 8 is hydrogen, (C C 6 -alkyl) or halogen
  • T 9 is nitro, cyano, -COCH 3 or COOT 11 , where T 11 is (C C 4 )-alkyl; or represent a group of formula (IVe)
  • T 7 and T 8 are each as defined above; or represent a group of formula (IVf)
  • T 13 is phenyl or -S-(CrC 4 )-alkyl.
  • Alkyl groups may be straight-chain or branched in the context of the present invention.
  • CrC 6 -Alkyl is for example methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or n-hexyl.
  • alkoxy groups which are methoxy or ethoxy for example.
  • Ci-C 6 -alkyl groups can be monovalent hydrocarbyl radicals or cyano, thiocyanato, nitro, hydroxyl, alkoxy, carboxyl, sulfonic acid, carboxylic ester, carboxamide or amino groups as well as halogen atoms.
  • Monovalent hydrocarbyl radicals include alkyl, cycloalkyl, aryl or heterocyclyl radicals.
  • (C 3 -C 4 )-Alkenyl groups are in particular allyl.
  • Substituents for (C 3 -C )-alkenyl are for example halogen and phenyl.
  • Aryl is in particular phenyl or naphthyl.
  • Aryloxy is in particular naphthyloxy or phenyloxy.
  • Substituents for aryl or aryloxy are for example halogen, methyl, ethyl, hydroxyethyl, methoxy, ethoxy, hydroxyl, nitro and cyano.
  • -NHS0 2 -Aryl is in particular phenylsulfonylamino.
  • Halogen is fluorine, chlorine, bromine or iodine, preferably chlorine or bromine.
  • R 1 is preferably hydrogen, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl, methoxy, ethoxy, hydroxyl, chlorine, bromine, -NHCHO, -NHCO-methyl, -NHCO- phenyl, -NHS0 2 -methyl or -NHS0 2 -phenyl.
  • Very particularly preferred R 1 radicals are hydrogen, -NHCO-methyl, methyl and hydroxyl.
  • R 2 is preferably hydrogen, chlorine, bromine, methoxy, ethoxy, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl or phenoxy.
  • Very particularly preferred R 2 radicals are hydrogen and methoxy.
  • R 3 is preferably hydrogen, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl, 2-cyanoethyl, vinyl, allyl, benzyl or a radical of formula -CHR 4 -C n H 2n -CHR 6 -COO- CHR 7 -CO-R 5 .
  • Very particularly preferred R 3 radicals are hydrogen, benzyl,
  • R 4 is preferably hydrogen, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl or phenyl.
  • Very particularly preferred R 4 radicals are hydrogen and methyl.
  • R 5 is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or substituted (C C6)-alkyl, such as 2-cyanoethyl or cyanomethyl.
  • Methyl is a very particularly preferred R 5 radical.
  • R 6 is preferably hydrogen, methyl or ethyl. Hydrogen is a very particularly preferred R 6 radical.
  • R 7 is preferably hydrogen, methyl, ethyl or phenyl. Very particularly preferred R 7 radicals are hydrogen and methyl.
  • R 8 is preferably hydrogen, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl, methoxy, ethoxy, hydroxyl, chlorine, bromine, -NHCHO, -NHCO-methyl, -NHCO- phenyl, -NHS0 2 -methyl or -NHSO 2 -phenyl.
  • Very particularly preferred R radicals are hydrogen, methyl, -NHCO-methyl and hydroxyl.
  • R 9 is preferably hydrogen, chlorine, bromine, methoxy, ethoxy, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl or phenoxy.
  • Very particularly preferred R 9 radicals are hydrogen, chlorine, methoxy and methyl.
  • R 10 is preferably hydrogen, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl, vinyl, allyl, benzyl or a radical of formula -CHR 11 -C m H 2m -(X) 0 -R 12 , where R 1 , R 12 , X, m and o are each as defined above.
  • R 1 1 is preferably hydrogen, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl or phenyl.
  • Very particularly preferred R 11 radicals are hydrogen or methyl.
  • R 12 is preferably hydrogen, methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl, benzyl, vinyl, allyl, 2-(N-phthalimidoyl)ethyl, cyanomethyl, 2-cyanoethyl or radicals of formula -C q H 2q -Y-C r H 2r (Z) 0 -R 13 , where q is 1 , 2, 3 or 4, r is 1 , 2, 3 or 4, o is 0 or , Y is -CO-, -COO- or -OCO-, Z is -COO- or -OCO- and R 13 is (d-C 6 )-alkyl, phenyl, halogen, cyano or heterocyclyl, especially N-phthalimidoyl.
  • X is preferably -CO-O-, -O-CO- or -O- R 13 is preferably cyano.
  • R 14 is preferably ethyl or more particularly methyl.
  • the index m is preferably 0 or 1.
  • the index n is preferably 0 or 1.
  • the index o is preferably 1. It is particularly preferable for the dye mixtures according to the present invention to utilize compounds of formula I where
  • R 1 is hydrogen, -NHCO-methyl, methyl or hydroxyl
  • R 2 is hydrogen or methoxy
  • R 3 is hydrogen, benzyl, 2-cyanoethyl, methyl, ethyl, n-propyl, n-butyl or
  • R 4 is hydrogen or methyl
  • R 5 is methyl
  • R 6 is hydrogen
  • R 7 is hydrogen or methyl
  • n O or l .
  • R 8 is hydrogen, methyl, -NHCO-methyl or hydroxyl
  • R 9 is hydrogen, chlorine, methoxy or methyl
  • R 11 is hydrogen or methyl
  • X is -CO-O-, -O-CO- or -0-
  • m 0 or 1.
  • R 13 is cyano
  • R 14 is ethyl or methyl
  • R 5 is methyl, ethyl, n-propyl, sec-propyl, n-butyl, sec-butyl, 1-ethylpentyl,
  • Preferred dye mixtures according to the present invention contain at least one dye of formula (I) where D 1 is a group of formula (IVa) in which
  • T 1 is nitro
  • T 2 is hydrogen or chlorine
  • T 3 is hydrogen, chlorine, bromine, trifluoromethyl, cyano or nitro
  • T 4 is hydrogen, chlorine, bromine, trifluoromethyl, cyano or nitro
  • R 1 is hydrogen, chlorine, methyl, acetylamino, propionylamino, benzoylamino; methylsulfonylamino, ethylsulfonylamino or phenylsulfonylamino,
  • R 2 is hydrogen or chlorine
  • R 3 is hydrogen, methyl, ethyl, propyl, butyl, benzyl, phenylethyl, phenoxyethyl, methoxyethyl, cyanoethyl or allyl,
  • R 4 , R 6 and R 7 are hydrogen
  • R 5 is methyl
  • n O or l .
  • Particularly preferred dye mixtures according to the present invention contain at least one dye of formula (I) where D 1 is a group of formula (IVa) in which
  • T 1 is nitro
  • T 2 is hydrogen or chlorine
  • T 3 is hydrogen, chlorine, bromine, trifluoromethyl, cyano or nitro
  • T 4 is hydrogen, chlorine, bromine, trifluoromethyl, cyano or nitro
  • R 1 is hydrogen, methyl or acetylamino
  • R 2 is hydrogen or chlorine
  • R 3 is hydrogen, methyl, ethyl, n-butyl, benzyl, phenylethyl, phenoxyethyl,
  • R 4 , R 6 and R 7 are hydrogen
  • R 5 is methyl
  • n 0.
  • Very particularly preferred dye mixtures according to the present invention contain at least one dye of formula (la)
  • T 2 is hydrogen or chlorine
  • T 3 is hydrogen, chlorine, bromine or cyano
  • T 4 is hydrogen, chlorine, bromine, cyano, nitro or trifluoromethyl
  • R 1 is hydrogen, -NHCOCH3 or -NHS0 2 CH 3 , and
  • R 2 is hydrogen or -OCH3.
  • dye mixtures according to the present invention contain at least one dye of formula (lla)
  • R 8 is hydrogen, (C C 6 )-alkyl, (Ci-C )-alkoxy, hydroxyl, halogen, -NHCHO, -NHCO(Ci-C 6 )-alkyl, -NHCO-aryl, -NHS0 2 (Ci-C 6 )-alkyl or -NHSO 2 -aryl, R 9 is hydrogen, halogen, (CrC4)-alkoxy, (Ci-C 4 )-alkyl or phenoxy,
  • R 10 is hydrogen, (C ⁇ CeJ-alkyl, substituted (C C 6 )-alkyl, (C 3 -C 4 )-alkenyl or substituted (C3-C 4 )-alkenyl, or R 9 and R 10 combine to form the moiety - C*H(CH3)CH2C(CH 3 ) 2 -, where the carbon atom marked * is attached to the phenyl nucleus,
  • R 1 is hydrogen, (C C6)-alkyl or phenyl
  • R 12 is hydrogen, (C C 6 )-alkyl, substituted (Ci-C 6 )-alkyl, (C 3 -C 4 )-alkenyl or substituted (C3-C 4 )-alkenyl,
  • n 0, 1 , 2 or 3, and
  • D 4 is a group of formula (IVa) and/or a dye of formula (Ilia)
  • R 13 is hydrogen, cyano or carboxamido
  • R 14 is methyl, ethyl or phenyl
  • R 15 is optionally substituted (Ci-Ce)-alkyl or optionally substituted oxygen
  • D 5 is a group of formula (IVa). Further very preferable dye mixtures according to the present invention contain at least one dye of formula (lib)
  • R 8 is hydrogen, (d-CeJ-alkyl, (Ci-C 4 )-alkoxy, hydroxyl, halogen, -NHCHO, -NHCO(C C 6 )-alkyl, -NHCO-aryl, -NHSO 2 (C 1 -C 6 )-alkyl or -NHSO 2 -aryl,
  • R 9 is hydrogen, halogen, (Ci-C 4 )-alkoxy, (Ci-C 4 )-alkyl or phenoxy,
  • R 10 is hydrogen, (Ci-C 6 )-alkyl, substituted (C C 6 )-alkyl, (C 3 -C 4 )-alkenyl or substituted (C3-C 4 )-alkenyl, or R 9 and R 10 combine to form the moiety -C * H(CH 3 )CH 2 C(CH 3 ) 2 -, where the carbon atom marked * is attached to the phenyl nucleus,
  • R 11 is hydrogen, (C-i-C6)-alkyl or phenyl
  • R 12 is hydrogen, (CrC 6 )-alkyl, substituted (Ci-C 6 )-alkyl, (C 3 -C 4 )-alkenyl or
  • n 0, 1 , 2 or 3
  • D 6 is a group of formula (IVa), where T 1 is nitro; and/or a dye of formula (Illb)
  • R 13 is hydrogen, cyano or carboxamido
  • R 14 is methyl, ethyl or phenyl
  • R 15 is optionally substituted (CrC 6 )-alkyl or optionally substituted oxygen- interrupted (C 2 -C6)-alkyl, and
  • D 7 is a group of formula (IVa), where T 1 is nitro or -OCH 3 .
  • Further very particularly preferred dye mixtures according to the present invention contain at least one dye of formula He
  • R 8 is hydrogen, methyl, methoxy, ethoxy, hydroxyl, chlorine, bromine,
  • R 9 is hydrogen, methyl, -OCH3, -OCH2CH3, chlorine or bromine,
  • R 10 is hydrogen, (CrC 6 )-alkyl or substituted (Ci-C 6 )-alkyl,
  • n 0, 1 , 2 or 3
  • T 2 is hydrogen
  • T 3 is hydrogen, chlorine, bromine, nitro, cyano or hydroxyl
  • T 4 is hydrogen, chlorine, bromine, nitro or cyano; and/or a dye of formula (lllc)
  • R 13 is hydrogen, cyano or carboxamido
  • R 14 is methyl, ethyl or phenyl
  • R 15 is optionally substituted (Ci-C 6 )-alkyl
  • D 9 is a group of formula (IVa), where
  • T is nitro or -OCH3,
  • T 2 is hydrogen
  • T 3 is hydrogen, chlorine, bromine, nitro or cyano or hydroxyl
  • T 4 is hydrogen, chlorine, bromine, nitro or cyano.
  • Particularly preferred dye mixtures according to the present invention contain at least one dye of formu
  • T 3 is hydrogen, chlorine, bromine or cyano
  • T 4 is cyano or nitro
  • R 1 is hydrogen or -NHCOCH 3 .
  • R 2 is hydrogen or -OCH 3 ; and also at least one dye of formula lid
  • R 8 is hydrogen, -NHCOCH 3 or -NHCOCH 2 CH 3 ,
  • R 9 is hydrogen, -OCH3 or -OCH 2 CH 5 ,
  • R 10 is hydrogen, (Ci-C 6 )-alkyl or substituted (Ci-C 6 )-alkyl,
  • R 12 is hydrogen, (CrC 6 )-alkyl or substituted (Ci-C 6 )-alkyl,
  • T 3 is hydrogen, chlorine, bromine, nitro, cyano or hydroxyl
  • T 4 is hydrogen, chlorine, bromine, nitro or cyano.
  • the dye mixtures according to the present invention contain the dyes of formula (I) in admixture with (II) or (III) more particularly in amounts each from 1% to 99% by weight, more preferably in amounts of in each case from 20% to 80% by weight.
  • Very particularly preferred dye mixtures according to the present invention contain dyes of formula (I) in amounts from 30% to 60% by weight and dyes of formula (II) or (III) in amounts from 40% to 70% by weight. This also applies mutatis mutandis to mixtures containing dyes of formulae la, lb or lc or of formulae lla, lib, lie or lid or of formulae Ilia, 1Mb or lllc, respectively.
  • Suitable mixing ratios for dye of formula (l):dye of formula (II) or of formula (III) are in the range from 90:10 to 10:90, more particularly 90:10, 80:20, 75:25, 70:30, 60:40, 55:45, 50:50, 45:55, 40:60, 30:70, 25:75, 20:80 and 10:90.
  • the dye mixtures according to the present invention are obtainable by mechanically mixing the dyes of formula (I) with dyes of formulae (II) or (III).
  • the amounts are more particularly chosen so as to produce mixtures having the desired compositions.
  • the dye mixtures according to the present invention are outstandingly useful for dyeing and printing hydrophobic materials in that the dyeings and prints obtained are notable for level shades and high service fastnesses. Deserving of particular mention are outstanding wash and contact fastnesses and also good sublimation fastnesses, especially on polyester and polyester-elastane materials.
  • the present invention thus also provides for the use of the dye mixtures of the present invention for dyeing and printing hydrophobic materials, i.e., processes for dyeing or printing such materials in a conventional manner wherein a dye mixture according to the present invention is used as a colorant.
  • the hydrophobic materials mentioned can be of synthetic or semisynthetic origin. Examples include secondary cellulose acetate, cellulose triacetate, polyamides, polylactides and more particularly high molecular weight polyesters. Materials composed of high molecular weight polyester are more particularly those based on polyethylene terephthalates or polytrimethylene terephthalates. Blend fabrics and blend fibers such as for example polyester-cotton or polyester-elastane are also possible.
  • the hydrophobic synthetic materials can be present in the form of self- supporting film/sheeting or fabric- or thread-shaped bodies and may for example have been processed into yarns or woven or knitted textile fabrics. Preference is given to fibrous textile materials, which may also be present in the form of microfibers for example.
  • the dyeing in accordance with the use provided by the present invention can be effected in a conventional manner, preferably from an aqueous dispersion, if appropriate in the presence of carriers, at between 80 to about 110°C by the exhaust process or in a dyeing autoclave at 1 0 to 140°C by the HT process, and also by the so-called thermofix process, in which the fabric is padded with the dyeing liquor and subsequently fixed/set at about 180 to 230°C.
  • Printing of the materials mentioned can be carried out in a manner known per se by incorporating the dye mixtures of the present invention in a print paste and treating the fabric printed therewith at temperatures between 180 to 230°C with HT steam, high-pressure steam or dry heat, if appropriate in the presence of a carrier, to fix the dye.
  • the dye mixtures of the present invention shall be in a very fine state of subdivision when they are used in dyeing liquors, padded liquors or print pastes.
  • the dyes are converted into the fine state of subdivision in a conventional manner by slurrying them together with dispersants in a liquid medium, preferably water, and subjecting the mixture to the action of shearing forces to mechanically comminute the originally present dye particles to such an extent that an optimal specific surface area is achieved and sedimentation of the dye is minimized. This is accomplished in suitable mills, such as ball or sand mills.
  • the particle size of the dyes is generally between 0.5 and 5 ⁇ , and preferably equal to about 1 m.
  • the dispersants used in the milling operation can be nonionic or anionic.
  • Nonionic dispersants are for example reaction products of alkylene oxides, for example ethylene oxide or propylene oxide, with alkylatable compounds, for example fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols and carboxamides.
  • Anionic dispersants are for example lignosulfonates, alkyl- or alkylarylsulfonates or alkylaryl polyglycol ether sulfates.
  • the dye preparations thus obtained shall be pourable for most applications.
  • the dye and dispersant content is limited in these cases.
  • the dispersions are adjusted to a dye content of up to 50 percent by weight and a dispersant content of up to about 25 percent by weight.
  • dye contents are in most cases not below 15 percent by weight.
  • the dispersions may also contain still further auxiliaries, for example those which act as an oxidizing agent, for example sodium m-nitrobenzenesulfonate, or fungicidal agents, for example sodium o-phenylphenoxide and sodium pentachlorophenoxide, and particularly so-called "acid donors", examples being butyrolactone,
  • monochloroacetamide sodium chloroacetate, sodium dichloroacetate, the sodium salt of 3-chloropropionic acid
  • monosulfate esters such as lauryl sulfate for example
  • sulfuric esters of ethoxylated and propoxylated alcohols for example butylglycol sulfate.
  • the dye dispersions thus obtained are very advantageous for making up dyeing liquors and print pastes.
  • powder formulations contain the dye, dispersants and other auxiliaries, for example wetting, oxidizing, preserving and dustproofing agents and the abovementioned "acid donors”.
  • a preferred method of making pulverulent dye preparations consists in stripping the above-described liquid dye dispersions of their liquid, for example by vacuum drying, freeze drying, by drying on drum dryers, but preferably by spray drying.
  • the dyeing liquors are made by diluting the requisite amounts of the above-described dye formulations with the dyeing medium, preferably water, such that an appropriate liquor ratio of, for example, 1 :5 to 1 :50 is obtained for dyeing.
  • the dyeing medium preferably water
  • further dyeing auxiliaries such as dispersing, wetting and fixing auxiliaries, to the liquors.
  • Organic and inorganic acids such as acetic acid, succinic acid, boric acid or phosphoric acid are added to set a pH in the range from 4 to 5, preferably 4.5. It is advantageous to buffer the pH setting and to add a sufficient amount of a buffering system.
  • the acetic acid/sodium acetate system is an example of an advantageous buffering system.
  • the present invention also provides inks for digital textile printing by the ink jet process, said inks containing a dye mixture according to the present invention.
  • the inks of the present invention are preferably aqueous and contain dye mixtures of the present invention in amounts ranging for example from 0.1 % to 50% by weight, preferably in amounts ranging from 1% to 30% by weight and more preferably in amounts ranging from 1 % to 15% by weight based on the total weight of the ink.
  • Suitable dispersants are known to a person skilled in the art, are commercially available and include for example sulfonated or sulfomethylated lignins,
  • condensation products of aromatic sulfonic acids and formaldehyde condensation products of optionally substituted phenol and formaldehyde, polyacrylates and corresponding copolymers, modified polyurethanes and reaction products of alkylene oxides with alkylatable compounds, for example fatty alcohols, fatty amines, fatty acids, carboxamides and optionally substituted phenols.
  • the inks according to the present invention may further contain the customary additives, for example viscosity moderators to set viscosities in the range from 1.5 to 40.0 mPas in the temperature range from 20 to 50°C.
  • Preferred inks have a viscosity in the range from 1.5 to 20 mPas and particularly preferred inks have a viscosity in the range from 1.5 to 15 mPas.
  • Suitable viscosity moderators are rheological additives, for example polyvinyl caprolactam, polyvinylpyrrolidone and also their copolymers, polyetherpolyol, associative thickeners, polyurea, sodium alginates, modified galactomannans, polyetherurea, polyurethane and nonionic cellulose ethers.
  • the inks according to the present invention may contain surface-active substances to set surface tensions in the range from 20 to 65 mN/m, which are adapted as appropriate depending on the process used (thermal or piezo technology).
  • Suitable surface-active substances are for example surfactants of any kind, preferably nonionic surfactants, butyldiglycol and 1 ,2-hexanediol.
  • the inks may further contain customary additions, for example substances to inhibit fungal and bacterial growth in amounts from 0.01% to 1% by weight based on the total weight of the ink.
  • the inks according to the present invention are obtainable in a conventional manner by mixing the components in water.
  • the mixture is ground as a 40% aqueous suspension with 100 parts of a high temperature stable dispersant until the particle size (diameter) has reached the size magnitude of 0.1 -5 micrometers.
  • This dispersion is standardized to a solid product containing 25% of the dye mixture and 70% dispersant, by adding 99.7 parts of a "cutting agent" and by drying in a spray dryer either in powder form.
  • 2 g of the dye mixture obtained as per a) are dispersed in 100 ml of water at 40 - 50°C.
  • a dyebath is prepared from 11.5 ml of this aqueous dispersion, 57.5 ml of deionized water and 1.2 ml of buffering solution (pH 4.5) and entered with a 5 g piece of polyester.
  • the dyebath is heated to 130°C and maintained at 130°C for 45 minutes in a Werner Mathis high temperature dyeing machine. After rinsing with water and reduction clearing, the polyester material has a ruby red hue having excellent wash fastnesses.
  • a particularly interesting property of this mixture is the outstanding wash and contact fastness and the good sublimation fastness on polyester and polyester microfiber.
  • Example 1 is repeated in similar fashion to obtain the dye mixtures of examples 2 to 20 according to the invention and use them for dyeing polyester.
  • the table which follows indicates the fraction of the respective dye in % by weight based on the total dye content. The indicated mixtures produce red dyeings having outstanding wash and contact fastnesses and also good sublimation fastness.
  • Further dye mixtures according to the present invention may contain the dyes of examples 21 to 29 and also be used for dyeing polyester.
  • the table which follows indicates the fraction of the respective dye in % by weight based on the total dye content. The indicated mixtures produce red dyeings having outstanding wash and contact fastnesses and also good sublimation fastness.
  • Further dye mixtures according to the present invention may contain the dyes of examples 30 to 49 and also be used for dyeing polyester.
  • the table which follows indicates the fraction of the respective dye in % by weight based on the total dye content. The indicated mixtures produce blue dyeings having outstanding wash and contact fastnesses and also good sublimation fastness.
  • the dye mixtures according to the present invention may contain the dyes of examples 50 to 69 and also be used for dyeing polyester.
  • the table which follows indicates the fraction of the respective dye in % by weight based on the total dye content. The indicated mixtures produce blue dyeings having outstanding wash and contact fastnesses and also good sublimation fastness.
  • Further dye mixtures according to the present invention contain the dyes of examples 70 to 89 and may be used for dyeing polyester.
  • the table which follows indicates the fraction of the respective dye in % by weight based on the total dye content. The indicated mixtures produce dyeings having outstanding wash and contact fastnesses and also good sublimation fastness.
  • a textile fabric consisting of polyester is pad-mangled with a liquor consisting of 50 g/l of an 8% sodium alginate solution, 100 g/l of an 8-12% carob flour ether solution and 5 g/l of monosodium phosphate in water and then dried.
  • the wet pickup is 70%.
  • the textile thus pretreated is printed with an aqueous ink prepared in accordance with the procedure described above and containing

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Coloring (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
PCT/EP2012/000049 2011-01-15 2012-01-07 Disperse dye mixtures, their preparation and use WO2012095284A1 (en)

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US13/979,756 US9096972B2 (en) 2011-01-15 2012-01-07 Disperse dye mixtures, their preparation and use
CN201280003182.7A CN103890103B (zh) 2011-01-15 2012-01-07 分散染料混合物及其制备和应用
MX2013005776A MX2013005776A (es) 2011-01-15 2012-01-07 Mezclas de tintes dispersos, su preparacion y uso.
BR112013017510-9A BR112013017510B1 (pt) 2011-01-15 2012-01-07 Misturas corantes dispersas, seu uso, e tinta para impressão têxtil digital através de um processo de jato de tinta
CA2806856A CA2806856C (en) 2011-01-15 2012-01-07 Disperse dye mixtures, their preparation and use
JP2013548779A JP5876508B2 (ja) 2011-01-15 2012-01-07 分散染料混合物、それらの調製物及び使用
KR1020137017606A KR101782194B1 (ko) 2011-01-15 2012-01-07 분산 염료 혼합물, 그의 제조 및 용도
EP12701666.5A EP2663600B1 (en) 2011-01-15 2012-01-07 Disperse dye mixtures, their preparation and use
ES12701666.5T ES2652518T3 (es) 2011-01-15 2012-01-07 Mezclas de colorantes dispersos, su preparación y uso

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DE102011008683A DE102011008683A1 (de) 2011-01-15 2011-01-15 Dispersionsfarbstoffmischungen, ihre Herstellung und Verwendung
DE102011008683.8 2011-01-15

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CN102942806A (zh) * 2012-11-17 2013-02-27 江苏德旺化工工业有限公司 一种分散蓝色染料
CN102993779A (zh) * 2012-12-20 2013-03-27 江苏之江化工有限公司 分散黑偶氮染料及其混合物
JP2016516097A (ja) * 2013-01-14 2016-06-02 ダイスター・カラーズ・ディストリビューション・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 高湿潤堅牢性の分散染料混合物
KR102287706B1 (ko) * 2013-01-14 2021-08-06 다이스타 컬러스 디스트리뷰션 게엠베하 고습윤 신속 분산 염료 혼합물
EP2754698A1 (en) * 2013-01-14 2014-07-16 DyStar Colours Distribution GmbH High wet-fast disperse dye mixtures
EP2754748A1 (en) * 2013-01-14 2014-07-16 DyStar Colours Distribution GmbH High wet fast disperse dye mixtures
WO2014108358A1 (en) 2013-01-14 2014-07-17 Dystar Colours Distribution Gmbh High wet fast disperse dye mixtures
KR20150108861A (ko) * 2013-01-14 2015-09-30 다이스타 컬러스 디스트리뷰션 게엠베하 고습윤 신속 분산 염료 혼합물
CN105102547A (zh) * 2013-01-14 2015-11-25 德司达染料分销有限公司 高湿牢度快速分散染料混合物
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JP2016513140A (ja) * 2013-01-14 2016-05-12 ダイスター・カラーズ・ディストリビューション・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 高湿潤堅牢性の分散染料混合物
CN113755026A (zh) * 2013-01-14 2021-12-07 德司达染料分销有限公司 高湿牢度快速分散染料混合物
EP2754697A1 (en) * 2013-01-14 2014-07-16 DyStar Colours Distribution GmbH High wet-fast disperse dye mixtures
JP2018083947A (ja) * 2013-01-14 2018-05-31 ダイスター・カラーズ・ディストリビューション・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 高湿潤堅牢性の分散染料混合物
JP2018076511A (ja) * 2013-01-14 2018-05-17 ダイスター・カラーズ・ディストリビューション・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 高湿潤堅牢性の分散染料混合物
US9534118B2 (en) 2013-01-14 2017-01-03 Dystar Colours Distribution Gmbh High wet fast disperse dye mixtures
KR102287714B1 (ko) * 2013-01-14 2021-08-06 다이스타 컬러스 디스트리뷰션 게엠베하 고습윤 신속 분산 염료 혼합물
EP3421550A1 (en) 2013-01-14 2019-01-02 DyStar Colours Distribution GmbH High wet fast disperse dye mixtures
US9493657B2 (en) * 2013-01-14 2016-11-15 Dystar Colours Distribution Gmbh AOX-free navy and black disperse dyes
KR102143259B1 (ko) * 2013-01-14 2020-08-10 다이스타 컬러스 디스트리뷰션 게엠베하 고습윤 신속 분산 염료 혼합물
KR20200096676A (ko) * 2013-01-14 2020-08-12 다이스타 컬러스 디스트리뷰션 게엠베하 고습윤 신속 분산 염료 혼합물
KR20200096675A (ko) * 2013-01-14 2020-08-12 다이스타 컬러스 디스트리뷰션 게엠베하 고습윤 신속 분산 염료 혼합물
CN103421350A (zh) * 2013-09-02 2013-12-04 杭州福莱蒽特精细化工有限公司 一种高水洗牢度分散黄棕染料组合物
US10611916B2 (en) * 2015-12-10 2020-04-07 Dystar Colours Distribution Gmbh High wet fast brilliant blue disperse dye mixtures
US20180273762A1 (en) * 2015-12-10 2018-09-27 Dystar Colours Distribution Gmbh High wet fast brilliant blue disperse dye mixtures

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US9096972B2 (en) 2015-08-04
BR112013017510A2 (pt) 2016-09-27
TWI661009B (zh) 2019-06-01
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JP5876508B2 (ja) 2016-03-02
EP2663600B1 (en) 2017-09-20
BR112013017510B1 (pt) 2020-10-20
MX2013005776A (es) 2013-06-28
CN103890103A (zh) 2014-06-25
DE102011008683A1 (de) 2012-07-19
ES2652518T3 (es) 2018-02-02
EP2663600A1 (en) 2013-11-20
CN103890103B (zh) 2018-03-06
WO2012095284A9 (en) 2012-09-07
CA2806856A1 (en) 2012-07-19
JP2014505768A (ja) 2014-03-06
TWI633158B (zh) 2018-08-21
CA2806856C (en) 2018-09-11
PT2663600T (pt) 2017-12-22
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