EP0432597B1 - Procédé de teinture de substrats en polyamide - Google Patents

Procédé de teinture de substrats en polyamide Download PDF

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Publication number
EP0432597B1
EP0432597B1 EP90123037A EP90123037A EP0432597B1 EP 0432597 B1 EP0432597 B1 EP 0432597B1 EP 90123037 A EP90123037 A EP 90123037A EP 90123037 A EP90123037 A EP 90123037A EP 0432597 B1 EP0432597 B1 EP 0432597B1
Authority
EP
European Patent Office
Prior art keywords
dyes
groups
dyeing
polyamide
azo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP90123037A
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German (de)
English (en)
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EP0432597A1 (fr
Inventor
Erwin Dr. Hahn
Alexander Dr. Aumueller
Wolfgang Dr. Reuther
Reinhold Krallmann
Dieter Dr. Wegerle
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BASF SE
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BASF SE
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Publication date
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6422—Compounds containing nitro or nitroso 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/241—Polyamides; Polyurethanes using acid dyes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/917—Wool or silk
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber

Definitions

  • the present invention relates to an improved process for dyeing polyamide substrates from aqueous baths with suitable dyes and with copper complexes as light stabilizers for the colored polyamide.
  • the invention further relates to dye formulations which contain a copper complex of an organic N-nitrosohydroxylamine as a light stabilizer for the colored polyamide.
  • colored polyamide loses lightfastness due to the catalytic influence of the dye, i.e. it is subject to chemical changes under the influence of light and especially light and heat, which deteriorate the mechanical and thermal properties and also cause undesirable discoloration.
  • lightfastness stabilizers have therefore been used in the coloring, which are primarily copper complexes, e.g. of salicylaldehydes (EP-A 252 368), salicyloximes (EP-A 113 856 and EP-A 162 811) and water-soluble azo dyes (EP-A 255 481) and of hydroxamic acids (DE-A 3 326 640).
  • copper complexes e.g. of salicylaldehydes (EP-A 252 368), salicyloximes (EP-A 113 856 and EP-A 162 811) and water-soluble azo dyes (EP-A 255 481) and of hydroxamic acids (DE-A 3 326 640).
  • the concentration in the dye bath must be chosen higher than the amount required, and moreover they have too strong their own color, so that they shift the color tone and brilliantly tarnish the dyeing, particularly in the case of brilliant dyeings.
  • the object of the invention was therefore to remedy these disadvantages.
  • the copper complexes to be used according to the invention which have the general structure I correspond and in which the radicals R are aliphatic, cycloaliphatic, araliphatic or aromatic organic groups, can in principle be derived from any organic N-nitrosohydroxylamines.
  • the cycloalkyl and aryl groups can in turn carry one to three substituents.
  • N-nitrosohydroxylamines on which the complexes are based are known or can be obtained in a known manner, e.g. by the action of nitrosating agents such as alkali metal nitrites on N-monosubstituted hydroxylamines (DE-A 10 19 657). The same applies to the production of the complexes.
  • Suitable dyes are azo and anthraquinone dyes, their metal complexes and also other metal complex dyes.
  • azo dyes mono- and bisazo dyes of benzene-azo-naphthalene, benzene-azo-1-phenylpyrazol-5-one, benzene-azo-benzene, naphthalene-azo-benzene, benzene-azo-aminonaphthalene are particularly suitable.
  • Particularly suitable disperse dyes are metal complex dyes, for example 1: 1 or preferably 1: 2 complexes of metallized azo, azomethine and phthalocyanine dyes.
  • Azo and azomethine dyes preferentially complex chromium or cobalt, phthalocyanines especially copper and nickel. Examples of the latter class of dyes are described in F.H. Moser, D.L. Thomas: The Phthalocyanines ", Vol. II, CRC Press, Boca Raton, Florida 1983.
  • the process according to the invention is suitable for dyeing any polyamides, e.g. also natural polyamides such as wool and silk, but is of particular practical importance for dyeing synthetic polyamides such as nylon 6, nylon 6.6 and nylon 12 or materials containing these polyamides.
  • the substrates can be of any shape - for example injection molded articles, foils, tapes and fibers, but primarily fiber structures such as yarns, nonwovens and mainly textiles come into consideration.
  • the dyeing process is carried out under the conditions recommended for the respective dyes, as usual, from an aqueous bath, so that detailed explanations for this are unnecessary.
  • the amount of copper complexes to be used according to the invention in the case of polyamide textile goods, is generally between 0.01 and 2% by weight of copper, depending on the type of fabric and the amount of dye applied, based on the amount of the polyamide content in the textile goods.
  • the concentration of the complex in the dyebath depends on this amount, which is expediently dimensioned in such a way that the used dyebath contains only 0.001 to 1% by weight of copper in the form of the complexes because of the excellent absorption capacity.
  • the effective amounts of dyes and complexes can be determined by means of a few preliminary tests.
  • the copper complexes are normally finished at the same time as the dyeing process, but it is also possible to apply the complexes to the substrate from a separate bath before or after the dyeing.
  • the process according to the invention is of great importance for the dyeing of textiles made of polyamides, which are not only exposed to light to a special degree but also to heat, which are primarily fabrics for the seats and interior linings of cars.
  • the lower intrinsic color of the complexes enables the fabrics to be colored in clearer shades than before.
  • the yarn dyed in this way is characterized by high light fastness and brilliant coloring.
  • the orange-brown dyeing obtained in this way showed a significantly improved light fastness in accordance with the fakrotest DIN 75 202 compared to a dyeing which had not been post-treated.
  • the gray color produced in this way showed, according to the facotest DIN 75 202, a significantly improved light fastness compared to a corresponding color without the addition of the copper complex.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Claims (5)

  1. Procédé de teinture de substats en polyamides à partir de bains aqueux avec des colorants convenant à cette fin, comme aussi avec des complexes de cuivre à titre de photostabilisateurs pour le polyamide teint, caractérisé en ce que l'on utilise à titre de complexes de cuivre pour la teinture, ceux obtenus avec des N-nitrosohydroxylamines organiques.
  2. Procédé suivant la revendication 1, caractérisé en ce que l'on utilise, à titre de complexes du cuivre, ceux qui répondent à la formule générale I
    Figure imgb0007
     dans laquelle les symboles R représentent des radicaux alkyle en C₁-C₂₀, des radicaux alcényle en C₃-C₂₀, des radicaux alkylaryle en C₇-C₁₂, des radicaux cycloalkyle en C₅-C₁₂, ou des radicaux aryle, où les radicaux cycloalkyle peuvent porter jusqu'à 3 radicaux alkyle en C₁-C₄ et les radicaux aryle peuvent porter jusqu'à 3 radicaux alkyle en C₁-C₁₂, radicaux alcoxy en C₁-C₁₂, radicaux alcényle en C₂-C₈, atomes de chlore, ou radicaux amino, à titre de substituants.
  3. Procédé suivant la revendication 2, caractérisé en ce que l'on utilise, pour la teinture, un composé I dans lequel les symboles R représentent des radicaux phényle ou cyclohexyle.
  4. Procédé suivant l'une quelconque des revendications 1 à 3, caractérisé en ce qu'on l'utilise pour la teinture d'objets plats, qui se composent de fibres de polyamide ou qui en contiennent.
  5. Préparations de teinture pour la teinture de substrats de polyamides, caractérisées en ce qu'elles contiennent, à titre de photostabilisateur pour le polyamide teint, un complexe du cuivre d'une N-nitrosohy-droxylamine organique.
EP90123037A 1989-12-14 1990-12-01 Procédé de teinture de substrats en polyamide Expired - Lifetime EP0432597B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3941295 1989-12-14
DE3941295A DE3941295A1 (de) 1989-12-14 1989-12-14 Verfahren zum faerben von polyamidsubstraten

Publications (2)

Publication Number Publication Date
EP0432597A1 EP0432597A1 (fr) 1991-06-19
EP0432597B1 true EP0432597B1 (fr) 1993-11-18

Family

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Family Applications (1)

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EP90123037A Expired - Lifetime EP0432597B1 (fr) 1989-12-14 1990-12-01 Procédé de teinture de substrats en polyamide

Country Status (4)

Country Link
US (1) US5076808A (fr)
EP (1) EP0432597B1 (fr)
JP (1) JPH03185186A (fr)
DE (2) DE3941295A1 (fr)

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US5681380A (en) 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5643356A (en) 1993-08-05 1997-07-01 Kimberly-Clark Corporation Ink for ink jet printers
US5721287A (en) 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
US5773182A (en) 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US5645964A (en) 1993-08-05 1997-07-08 Kimberly-Clark Corporation Digital information recording media and method of using same
US5865471A (en) 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US5700850A (en) 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
US6017471A (en) 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US5733693A (en) 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US6017661A (en) 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
CA2120838A1 (fr) 1993-08-05 1995-02-06 Ronald Sinclair Nohr Substance a couleur en aplat variable a l'ultraviolet
US6071979A (en) 1994-06-30 2000-06-06 Kimberly-Clark Worldwide, Inc. Photoreactor composition method of generating a reactive species and applications therefor
US6242057B1 (en) 1994-06-30 2001-06-05 Kimberly-Clark Worldwide, Inc. Photoreactor composition and applications therefor
US5739175A (en) 1995-06-05 1998-04-14 Kimberly-Clark Worldwide, Inc. Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer
US5685754A (en) 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and polymer coating applications therefor
US6008268A (en) 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
US5798015A (en) 1995-06-05 1998-08-25 Kimberly-Clark Worldwide, Inc. Method of laminating a structure with adhesive containing a photoreactor composition
ES2148776T3 (es) 1995-06-05 2000-10-16 Kimberly Clark Co Pre-colorantes y compuestos que los contienen.
US5747550A (en) 1995-06-05 1998-05-05 Kimberly-Clark Worldwide, Inc. Method of generating a reactive species and polymerizing an unsaturated polymerizable material
US5786132A (en) 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US5811199A (en) 1995-06-05 1998-09-22 Kimberly-Clark Worldwide, Inc. Adhesive compositions containing a photoreactor composition
US5849411A (en) 1995-06-05 1998-12-15 Kimberly-Clark Worldwide, Inc. Polymer film, nonwoven web and fibers containing a photoreactor composition
ATE206150T1 (de) 1995-06-28 2001-10-15 Kimberly Clark Co Farbstoffstabilisierte zusammensetzungen
US6391065B1 (en) 1995-11-03 2002-05-21 Boehme Filatex, Inc. UV light absorber composition and method of improving the lightfastness of dyed textiles
SK102397A3 (en) 1995-11-28 1998-02-04 Kimberly Clark Co Colorant stabilizers
US6099628A (en) 1996-03-29 2000-08-08 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5855655A (en) 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5782963A (en) 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
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US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
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US6228157B1 (en) 1998-07-20 2001-05-08 Ronald S. Nohr Ink jet ink compositions
US6045592A (en) * 1998-09-08 2000-04-04 Leanne Paquin Method and kit for dyeing shaped nylon plastics
EP1117698B1 (fr) 1998-09-28 2006-04-19 Kimberly-Clark Worldwide, Inc. Nouveaux photoamorceurs et leurs utilisations
ES2195869T3 (es) 1999-01-19 2003-12-16 Kimberly Clark Co Nuevos colorantes, estabilizantes de colorantes, compuestos de tinta y metodos mejorados para su fabricacion.
US6331056B1 (en) 1999-02-25 2001-12-18 Kimberly-Clark Worldwide, Inc. Printing apparatus and applications therefor
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Also Published As

Publication number Publication date
US5076808A (en) 1991-12-31
DE3941295A1 (de) 1991-06-20
EP0432597A1 (fr) 1991-06-19
JPH03185186A (ja) 1991-08-13
DE59003545D1 (de) 1993-12-23

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