EP0432597A1 - Procédé de teinture de substrats en polyamide - Google Patents

Procédé de teinture de substrats en polyamide Download PDF

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Publication number
EP0432597A1
EP0432597A1 EP90123037A EP90123037A EP0432597A1 EP 0432597 A1 EP0432597 A1 EP 0432597A1 EP 90123037 A EP90123037 A EP 90123037A EP 90123037 A EP90123037 A EP 90123037A EP 0432597 A1 EP0432597 A1 EP 0432597A1
Authority
EP
European Patent Office
Prior art keywords
groups
radicals
polyamide
dyes
complexes
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.)
Granted
Application number
EP90123037A
Other languages
German (de)
English (en)
Other versions
EP0432597B1 (fr
Inventor
Erwin Dr. Hahn
Alexander Dr. Aumueller
Wolfgang Dr. Reuther
Reinhold Krallmann
Dieter Dr. Wegerle
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BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0432597A1 publication Critical patent/EP0432597A1/fr
Application granted granted Critical
Publication of EP0432597B1 publication Critical patent/EP0432597B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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 it corresponds to the required amount, and moreover they have too strong their own color, so that they shift the color tone and brilliantly tarnish the dyeing, especially with 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.
  • Azo and anthraquinone dyes, their metal complexes and also other metal complex dyes come into consideration as 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 above all has 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 substance and the amount of dye applied, based on the amount of the polyamide content in the textile goods.
  • 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 particular 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 lightfastness 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)
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 true EP0432597A1 (fr) 1991-06-19
EP0432597B1 EP0432597B1 (fr) 1993-11-18

Family

ID=6395454

Family Applications (1)

Application Number Title Priority Date Filing Date
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
US5865471A (en) 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US5773182A (en) 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US5700850A (en) 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
US5733693A (en) 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US5645964A (en) 1993-08-05 1997-07-08 Kimberly-Clark Corporation Digital information recording media and method of using same
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US5721287A (en) 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
CA2120838A1 (fr) 1993-08-05 1995-02-06 Ronald Sinclair Nohr Substance a couleur en aplat variable a l'ultraviolet
US6017471A (en) 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US5643356A (en) 1993-08-05 1997-07-01 Kimberly-Clark Corporation Ink for ink jet printers
US6017661A (en) 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
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
US5685754A (en) 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and polymer coating applications therefor
US5739175A (en) 1995-06-05 1998-04-14 Kimberly-Clark Worldwide, Inc. Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer
US6008268A (en) 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
US5849411A (en) 1995-06-05 1998-12-15 Kimberly-Clark Worldwide, Inc. Polymer film, nonwoven web and fibers containing a photoreactor composition
US5786132A (en) 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US5798015A (en) 1995-06-05 1998-08-25 Kimberly-Clark Worldwide, Inc. Method of laminating a structure with adhesive containing a photoreactor composition
WO1996039646A1 (fr) 1995-06-05 1996-12-12 Kimberly-Clark Worldwide, Inc. Nouveaux pre-colorants
US5747550A (en) 1995-06-05 1998-05-05 Kimberly-Clark Worldwide, Inc. Method of generating a reactive species and polymerizing an unsaturated polymerizable material
US5811199A (en) 1995-06-05 1998-09-22 Kimberly-Clark Worldwide, Inc. Adhesive compositions containing a photoreactor composition
CA2221565A1 (fr) 1995-06-28 1997-01-16 Kimberly-Clark Worldwide, Inc. Colorants et modificateurs nouveaux
US6391065B1 (en) 1995-11-03 2002-05-21 Boehme Filatex, Inc. UV light absorber composition and method of improving the lightfastness of dyed textiles
US6099628A (en) 1996-03-29 2000-08-08 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5782963A (en) 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5855655A (en) 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
JPH10513502A (ja) 1995-11-28 1998-12-22 キンバリー クラーク ワールドワイド インコーポレイテッド 改良された着色剤安定剤
US5891229A (en) 1996-03-29 1999-04-06 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
PL338379A1 (en) 1998-06-03 2000-10-23 Kimberly Clark Co Novel photoinitiators and their application
EP1062285A2 (fr) 1998-06-03 2000-12-27 Kimberly-Clark Worldwide, Inc. Techniques recourant aux neonanoplastes et aux microemulsions relatives aux encres et a l'impression par jets d'encre
EP1100852A1 (fr) 1998-07-20 2001-05-23 Kimberly-Clark Worldwide, Inc. Compositions a jet d'encre ameliorees
US6045592A (en) * 1998-09-08 2000-04-04 Leanne Paquin Method and kit for dyeing shaped nylon plastics
ATE323725T1 (de) 1998-09-28 2006-05-15 Kimberly Clark Co Chelate mit chinoiden gruppen als photoinitiatoren
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
US6294698B1 (en) 1999-04-16 2001-09-25 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6368395B1 (en) 1999-05-24 2002-04-09 Kimberly-Clark Worldwide, Inc. Subphthalocyanine colorants, ink compositions, and method of making the same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2054661A1 (en) * 1970-11-06 1972-05-10 Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen N-nitrosa-n-aryl-hydroxylamines prepn - from nitrosa-arenes and nitrogen oxide
FR2251600A1 (fr) * 1973-11-19 1975-06-13 Basf Farben & Fasern

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US4707161A (en) * 1983-07-23 1987-11-17 Basf Aktiengesellschaft Lightfastness of dyeings obtained with acid dyes or metal complex dyes on polyamides: treatment with copper hydroxamates
DE3326640A1 (de) * 1983-07-23 1985-01-31 Basf Ag, 6700 Ludwigshafen Verfahren zur verbesserung der lichtechtheit von faerbungen mit saeure- oder metallkomplexfarbstoffen auf polyamid
DE3573626D1 (en) * 1984-05-22 1989-11-16 Ciba Geigy Ag Process for the photochemical stabilisation of materials containing polyamide fibres
DE3622864A1 (de) * 1986-07-08 1988-01-21 Bayer Ag Verfahren zur verbesserung der lichtechtheit von polyamidfaerbungen
US4874391A (en) * 1986-07-29 1989-10-17 Ciba-Geigy Corporation Process for photochemical stabilization of polyamide fiber material and mixtures thereof with other fibers: water-soluble copper complex dye and light-stabilizer
EP0362139B1 (fr) * 1988-09-29 1993-10-13 Ciba-Geigy Ag Procédé de stabilisation photochimique de matière fibreuse teinte et non teinte en polyamide et ses mélanges
US4902299A (en) * 1989-02-28 1990-02-20 E. I. Du Pont De Nemours And Company Nylon fabrics with cupric salt and oxanilide for improved dye-lightfastness

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2054661A1 (en) * 1970-11-06 1972-05-10 Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen N-nitrosa-n-aryl-hydroxylamines prepn - from nitrosa-arenes and nitrogen oxide
FR2251600A1 (fr) * 1973-11-19 1975-06-13 Basf Farben & Fasern

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TEXTILVEREDLUNG. vol. 20, no. 11, November 1985, BASEL CH Seiten 346 - 351; REINERT: "Lichtstabilität und Lichtstabilisierung von Polyamidfasern." *

Also Published As

Publication number Publication date
DE59003545D1 (de) 1993-12-23
US5076808A (en) 1991-12-31
JPH03185186A (ja) 1991-08-13
DE3941295A1 (de) 1991-06-20
EP0432597B1 (fr) 1993-11-18

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