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
• • 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
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
  • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
• • 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
• • 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
  • C09B67/0055—Mixtures of two or more disazo 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
  • D06P3/02—Material containing basic nitrogen
  • D06P3/04—Material containing basic nitrogen containing amide groups
  • D06P3/24—Polyamides; Polyurethanes
• • 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
  • D06P3/02—Material containing basic nitrogen
  • D06P3/04—Material containing basic nitrogen containing amide groups
  • D06P3/24—Polyamides; Polyurethanes
  • D06P3/241—Polyamides; Polyurethanes using acid dyes

Definitions

• the present invention relates to a process for the trichromatic dyeing or printing of natural or synthetic polyamide fibres or such fibres as contain polyamide with dye mixtures and also to such dye mixtures and polyamide fibres dyed or printed therewith.
• Trichromatic describes the additive colour mixing of suitable yellow- or orange-, red- and blue-dyeing dyes with which any desired shade in the visible spectrum can be obtained by suitably selecting the amount ratios for the dyes.
• Trichromatic dyeing is well known from the literature for various dye classes, for example from EP 83299, DE 2623178, EP 226982 and EP 808940.
• Optimum trichromatic performance of any yellow, red and blue dye mixture is crucially dependent on the neutral affinity and migration characteristics.
• Dyes having identical or very similar characteristic with regard to neutral affinity and migration are highly compatible with regard to trichromatic performance.
• Combinations of dyes having good trichromatic properties are known for monosulphonated acid dyes.
• no such dye mixtures are known to date for disulphonated acid dyes, for example the Nylosan® F dyes from Clariant.
• A is a hydrogen atom or a discretionary substituent
• R is a discretionarily substituted alkyl, cycloalkyl or aryl radical
• B is hydrogen; alkyl; hydroxyl-, alkoxy-, alkanoyloxy- or phenoxy-substituted alkyl, aralkyl, cycloalkyl or unsubstituted or alkyl-, halogen-, alkoxy-, nitro-, cyano-, alkoxycarbonyl-, carbamoyl- or sulphamoyl-substituted phenyl,
• R 4 is hydrogen; alkyl of 1-8 carbon atoms which may be interrupted by oxygen atoms and may be substituted by hydroxyl, acyloxy, alkoxy, cyano, cyclo-alkoxy, aralkoxy or aroxy; unsubstituted or hydroxyl-, chlorine-, hydroxy-alkyl-, chloroalkyl- or alkyl-substituted cycloalkyl or polycycloalkyl radicals of 5 to 15 carbon atoms; aralkyl radicals of 7 to 15 carbon atoms or unsubstituted or chlorine-, hydroxyl-, alkoxy-, alkyl-, hydroxyalkyl- or hydroxy-alkoxy-substituted phenyl radicals and also alkenyl, pyrrolidonylalkyl and carbonylalkyl radicals,
• R 1 is hydrogen; alkyl of 1-8 carbon atoms or hydroxyalkyl of 2 to 9 carbon atoms, and
• R 4 and R 1 combine with the nitrogen to form the radical of pyrrolidine, of piperidine or of morpholine and independently
• R 2 has the same meanings as R 4 ,
• R 3 has the same meanings as R 1 and
• R 2 and R 3 together have the same meanings as R 4 and R 1 together,
• Y is hydrogen; cyano; chlorine; bromine; methyl sulphone; ethyl sulphone; phenyl sulphone; carbalkoxy or —SO 3 H,
• Y 1 is hydrogen; chlorine; bromine or —SO 3 H,
• Y 2 is hydrogen; chlorine; bromine; methyl; carbalkoxy; 2-benzothiazolyl or —SO 3 H,
• R 1 to R 4 and Y to Y 2 together contain at least 2 sulphonic acid groups
• R 5 is hydrogen; C 1-4 alkyl or C 2-4 -hydroxyalkyl
• R 6 is hydrogen; C 1-4 alkyl; C 1-4 alkoxy; —NHCOC 1-4 alkyl; —NHCOOC 1-4 alkyl or —NHCONH 2 ,
• R 7 is hydrogen; halogen; C 1-4 alkyl or C 1-4 alkoxy and
• R 8 is hydrogen; C 1-4 alkyl; C 1-4 alkoxy or halogen;
• R 9 is chlorine; hydroxyl or NHCN,
• R 10 is hydrogen; chlorine or cyano
• R 11 is hydrogen; C 1-12 alkyl; hydroxyl-monosubstituted or -disubstituted C 2-8 alkyl, phenyl, phenyl(C 1-4 alkyl) or cyclohexyl and
• R 12 is unsubstituted or halogen-substituted, hydroxyl-monosubstituted or -disubstituted, phenyl-substituted, carboxyl-substituted or C 1-12 alkoxy-substituted C 4-20 alkyl; —G—O—C 1-12 alkyl, where G is C 2-3 alkylene; phenyl or phenyl(C 1-3 alkyl), whose phenyl ring is unsubstituted or substituted by one to three substituents selected from the group consisting of halogen, C 1-16 alkyl, C 2-6 hydroxyalkyl, C 1-6 alkoxy, phenoxy and —NHCOCH 3 ; or is cycionexyl which is unsubstituted or substituted by one to three C 1-4 alkyl groups,
• each R 13 is independently hydrogen, C 1-4 alkyl or halogen
• R 14 is hydrogen or substituted or unsubstituted C 1-4 alkyl
• R 15 independently has the same meanings as R 14 or
• R 14 and R 15 combine to form a cycloaliphatic ring of 5-8 carbon atoms
• R 16 is hydrogen or hydroxyl
• R 17 independently has the same meanings as R 16 ,
• E represents an aromatic, araliphatic, hydroaromatic radical or two aromatic radicals
• Z represents hydrogen or a discretionary substituent except sulphonic acid and carboxylic acid groups
• n 1 or 2
• a preferred trichromatic dyeing process comprises, as well as at least one anionic and/or nonionic dyeing auxiliary, using dye mixtures consisting of at least one blue-dyeing compound as per the formula (I) where A is a hydrogen atom or a discretionarily substituted alkyl or aryl radical, and at least one yellow-dyeing compound as per the formula (II) where
• B is hydrogen; alkyl; hydroxyl-, alkoxy-, alkanoyloxy or phenoxy-substituted alkyl,
• R 4 is hydrogen or alkyl of 1-8 carbon atoms which may be interrupted by oxygen atoms and may be substituted by hydroxyl, acyloxy, alkoxy, cyano, cycloalkoxy, aralkoxy or aroxy,
• R 2 is hydrogen; alkyl of 1-8 carbon atoms which may be interrupted by oxygen atoms and may be aryl radicals of 7 to 15 carbon atoms and
• Y is hydrogen; chlorine; bromine or —SO 3 H,
• Y 1 is hydrogen; chlorine; bromine; methyl or —SO 3 H,
• Y 2 is hydrogen; chlorine; bromine; methyl or —SO 3 H,
• R 5 is hydrogen or methyl
• R 6 is hydrogen; methyl; C 1-4 alkoxy; —NHCOCH 3 or —NHCONH 2 ,
• R 7 is hydrogen; methyl and
• R 8 is hydrogen; methyl; methoxy and
• R 9 is chlorine; hydroxyl or NHCN,
• R 10 is hydrogen; chlorine or cyano
• R 11 is hydrogen; C 1-4 alkyl; hydroxyl-monosubstituted or -disubstituted C 2-4 alkyl or phenyl and
• R 12 is unsubstituted or phenyl-monosubstituted C 4-14 alkyl; —G1—O—C 6-12 alkyl, where G1 is linear C 2-3 alkylene; C 6-16 alkyl- or phenoxy-monosubstituted phenyl; phenyl-(C 1-2 alkyl) whose phenyl ring is unsubstituted or monosubstituted by C 6 1-4 alkyl; or cyclohexyl substituted by one to three methyl groups,
• each R′ 13 is independently hydrogen or a C 1-4 alkyl group
• R 14 and R 15 have the meanings defined above
• R 18 is hydrogen or substituted or unsubstituted C 1-4 alkyl
• R 19 independently has the same meanings as R 18 ,
• n 1 or 2.
• a further likewise preferred trichromatic dyeing process comprises, as well as at least one anionic and/or nonionic dyeing auxiliary, using dye mixtures whose red component is a mixture of at least one red component of the formula (III) and at least one red component of the formula (IV).
• a further likewise preferred trichromatic dyeing process comprises, as well as at least one anionic and/or nonionic dyeing auxiliary, using dye mixtures whose red component is a mixture of at least one red component of the formula (III) and at least one red component of the formula (V).
• a further likewise preferred trichromatic dyeing process comprises, as well as at least one anionic and/or nonionic dyeing auxiliary, using dye mixtures whose red component is a mixture of at least one red component of the formula (IV) and at least one red component of the formula (V).
• a more preferred trichromatic dyeing process comprises, as well as at least one anionic and/or nonionic dyeing auxiliary, using dye mixtures containing at least one blue-dyeing compound as per the formula (I), where A is a hydrogen atom and R is a discretionarily substituted aryl radical and at least one yellow-dyeing compound as per the formula (II) where
• B is hydrogen or methyl
• R 4 is hydrogen or alkyl of 1-4 carbon atoms
• R 1 is nydrogen or alkyl of 1-4 carbon atoms
• R 2 is hydrogen; alkyl of 1-4 carbon atoms or aralkyl radicals of 7 to 15 carbon atoms,
• R 3 is hydrogen or methyl
• Y is hydrogen or chlorine
• Y 1 is hydrogen or chlorine
• Y 2 is hydrogen or —SO 3 H
• R 5 is hydrogen or methyl
• R 6 is hydrogen or methyl
• R 8 is hydrogen or methyl
• R 9 is chlorine or hydroxyl
• R 11 is hydrogen or methyl
• R 12 is unsubstituted or phenyl-monosubstituted C 4-14 alkyl
• R 18 is hydrogen or methyl
• R 19 independently has the same meanings as R 18 .
• Useful salts include in particular alkali metal, alkaline earth metal or ammonium salts or the salts of an organic amine.
• alkyl groups can be linear or branched.
• This invention further provides dye mixtures for the trichromatic dyeing or printing of natural or synthetic polyamide fibre material or such polyamide-containing material which are used in the above processes according to the invention.
• the inventive process for trichromatic dyeing or printing can be applied to all customary and known dyeing and printing processes, for example the continuous process, the exhaust process, the foam dyeing process and the ink-jet process.
• composition of the individual dye components in the trichromatic dye mixture used in the process according to the invention depends on the desired hue.
• a brown hue preferably utilizes 55-65% by weight of the yellow component according to the invention, 20-30% by weight of the red component according to the invention and 10-20% by weight of the blue component according to the invention.
• the red component as described above, can consist of a single component or of a mixture of different red individual components which conform to the formulae (III), (IV) and (V). Preference is given to double and triple combinations. It is to be noted that the components of the individual red components of the formulae (III)-(V) can themselves be mixtures.
• the fraction of the compounds of the formula (III) should not exceed 40% by weight based on the triple red mixture.
• the total amount of dyes in the process according to the invention is between 0.01 and 15% by weight, preferably between 1 and 10% by weight.
• the dye mixtures according to the invention, as well as the dyes and the water, further contain anionic or nonionic dyeing or printing auxiliaries.
• auxiliaries are in particular wetting agents, antifoams, levelling agents, thickeners and plasticizers.
• the present invention further provides substrates consisting of natural or synthetic polyamide or polyamidic substrates dyed or printed by a dye mixture according to the invention.
• the process according to the invention provides dyeings and prints having a homogeneous hue build-up throughout the entire hue spectrum with on-tone exhaustion, with a high bath exhaustion even in the case of fibres with low saturation and with a high dye build-up on fine fibres, particularly on microfibres.
• the resulting dyeings or prints are notable for very high wet fastnesses, specifically the fastnesses in washing, perspiration and water. These good wet and fabrication fastnesses, which are in no way inferior to the fastness level of dyeings and prints with metal complexes, are obtained without aftertreatment. With an additional aftertreatment, these fastnesses are even exceeded.
• a 20 g polyamide fabric is dyed in a liquor ratio of 10:1 with the following additions: 0.5% of a yellow dye as per Example 5, 0.1% of a red dye as per Example 13, 0.1% of a red dye as per Example 16, 0.05% of a red dye as per Example 7, 0.15% of a blue dye as per Example 2, 1.0% of an anionic oil sulphonate and 1.0 gl of sodium acetate
• the pH is adjusted to 4.5 with acetic acid.
• the liquor is heated to 70° C. at 2° C./min and subsequently dyed to 98° C. with 0.8° C./min. This is followed by cooling after 30 min and rinsing on attainment of 70° C. Drying without aftertreatment with a fixative provides a level brown dyeing possessing high household wash, perspiration and water fastness.
• a 20 g wool fabric is dyed in a liquor ratio of 20:1 with the following additions: 0.32% of a yellow dye as per Example 5 0.06% of a red dye as per Example 13 0.06% of a red dye as per Example 16 0.06% of a red dye as per Example 7 0.5% of a blue dye as per Example 2 1.0% of an anionic oil sulphonate 1.0% of an anionic fatty amine polyglycol ether 1.0 g/l of sodium acetate
• the pH is adjusted to 4.5 with acetic acid.
• the dyeing operation corresponds to that of Example 1. It provides a grey wool fabric having good perspiration and water fastnesses.
• a 20 g 90/10 PA/elastomer blend is dyed and finished similarly to Use Example 1.
• the dyeing possesses very good wash and perspiration fastnesses.
• a PA carpet is padded to a 100% pick-up with the following liquor: 2.5 g/l of a yellow dye as per Example 5 0.36 g/l of a red dye as per Example 13 0.36 g/l of a red dye as per Example 16 0.18 g/l of a red dye as per Example 7 1.7 g/l of a blue dye as per Example 2 2.0 g/l of a polyglycol ether sulphonate 4.0 g/l of a commercially available thickener based on bean flour ether
• the pH is adjusted to 6 with acetic acid.
• the carpet is then printed with a print paste containing the following components: 20.0 g/kg of a commercially available cationic fatty acid alkyl amine 20.0 g/kg of a commercially available thickener based on bean flour ether whose pH has been adjusted to 8 with sodium carbonate.
• the coloured carpet is fixed in saturated steam for 5 min, rinsed and dried.
• the white/olive-green carpet obtained has very good wet fastnesses.
• a PA fabric is printed with the following printing batches: 0.2 g/kg of a yellow dye as per Example 5 1.7 g/kg of a blue dye as per Example 2 0.6 g/kg of a red dye as per Example 13 0.6 g/kg of a red dye as per Example 16 0.3 g/kg of a red dye as per Example 7 10.0 g/kg of glycol ether 20.0 g/kg of urea 399.3 g/kg of boiling water 500.0 g/kg of bean flour ether thickener 60.0 g/kg of ammonium sulphate 5.0 g/kg of defoamer 1000 g total
• Printing is followed by 30 min of fixing with saturated steam at 102° C. and then by rinsing and drying.
• the print obtained is violet and possesses high wet fastness.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Coloring (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Pyrane Compounds (AREA)
• Ink Jet Recording Methods And Recording Media Thereof (AREA)

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• 2001
  • 2001-09-28 WO PCT/IB2001/001795 patent/WO2002046318A1/en active IP Right Grant
  • 2001-09-28 US US10/433,449 patent/US20040049863A1/en not_active Abandoned
  • 2001-09-28 CN CNB018200605A patent/CN1243794C/zh not_active Expired - Fee Related
  • 2001-09-28 NZ NZ525331A patent/NZ525331A/en not_active IP Right Cessation
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  • 2001-09-28 DE DE60112964T patent/DE60112964T2/de not_active Expired - Lifetime
  • 2001-09-28 AU AU9018501A patent/AU9018501A/xx active Pending
  • 2001-09-28 PT PT01970069T patent/PT1341853E/pt unknown
  • 2001-09-28 BR BRPI0115909-7B1A patent/BR0115909B1/pt not_active IP Right Cessation
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  • 2001-09-28 MX MXPA03004863A patent/MXPA03004863A/es active IP Right Grant
  • 2001-09-28 EP EP01970069A patent/EP1341853B1/en not_active Expired - Lifetime
  • 2001-09-28 AU AU2001290185A patent/AU2001290185B8/en not_active Ceased
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• 2003
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