EP0245204A1 - Procédé de stabilisation photochimique de matière fibreuse en polyamide teinté ou non teinté et ses mélanges avec d'autres fibres - Google Patents

Procédé de stabilisation photochimique de matière fibreuse en polyamide teinté ou non teinté et ses mélanges avec d'autres fibres Download PDF

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EP0245204A1
EP0245204A1 EP87810272A EP87810272A EP0245204A1 EP 0245204 A1 EP0245204 A1 EP 0245204A1 EP 87810272 A EP87810272 A EP 87810272A EP 87810272 A EP87810272 A EP 87810272A EP 0245204 A1 EP0245204 A1 EP 0245204A1
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alkyl
hydrogen
formula
hydroxy
radical
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EP0245204B1 (fr
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Gerhard Reinert
Kurt Burdeska
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Novartis AG
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Ciba Geigy AG
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/12—Aldehydes; Ketones
    • D—TEXTILES; PAPER
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    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/84—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising combined with mechanical treatment
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    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/12—Aldehydes; Ketones
    • D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
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    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
    • D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
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    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35—Heterocyclic compounds
    • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
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    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
    • D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
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    • 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
    • D06P1/62—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 with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/621—Compounds without nitrogen
    • D06P1/622—Sulfonic acids or their salts
    • D06P1/625—Aromatic
    • D—TEXTILES; PAPER
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    • 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
    • D06P1/6426—Heterocyclic compounds
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    • 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
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
    • D06P1/6497—Amides of di- or polyamines; Acylated polyamines
    • 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
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • 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
    • D06P1/651—Compounds without nitrogen
    • D06P1/65168—Sulfur-containing compounds
    • D06P1/65187—Compounds containing sulfide or disulfide 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
    • 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
    • D06P1/653—Nitrogen-free carboxylic acids or their salts
    • D06P1/6536—Aromatic
    • 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
    • D06P1/667—Organo-phosphorus compounds
    • 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
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber

Definitions

  • the present invention relates to a process for the photochemical stabilization of undyed and dyed polyamide fiber material and its blends with other fibers by treatment with organic copper complexes, light stabilizers and antioxidants.
  • copper salts e.g. Copper sulfate
  • inorganic or organic copper salts often have the disadvantage that they are insufficiently and unevenly drawn onto the polyamide fiber and therefore have to be used in high concentrations in order to achieve the desired effect achieve. Usually they can only be used as post-treatment and in discontinuous procedures.
  • EP-A 51 188 recommends treating the polyamide material before, during or after the dyeing with a mixture of copper complexes of bisazomethines and light stabilizers to improve the lightfastness of polyamide dyeings.
  • EP-A 162 811 and Textilveredlung 20 (1985), No. 11, pages 346-357 disclose the use of non-coloring, dye bath-stable, fiber-affine copper complex compounds for light or. Light-heat stabilization of dyeings on polyamide fibers is known. The improvements in authenticity and properties thus achieved currently satisfy e.g. claims made by the auto industry.
  • Non-coloring copper complexes of bisazomethines, acylhydrazones, semicarbazones or thiosemicarbazones of aromatic aldehydes or ketones or oximes are suitable as component A).
  • Such compounds have an excellent affinity for polyamide fiber material and if they have water-solubilizing groups they are also well water-soluble. They are therefore effective in extremely small amounts.
  • Bisazomethines of aromatic aldehydes or ketones are understood to mean Schiff bases of aliphatic or aromatic diamines, the aldehydes and ketones having an HO group in the o-position to the formyl or acyl radical.
  • the bond with the metal atom takes place via these two HO groups and the two nitrogen atoms in the bisazomethine part. Accordingly, these are tidentate ligands.
  • the ligands can contain one or more sulfo groups which are located in the aldehyde or ketone part and / or in the bisazomethine bridge.
  • Copper complexes of the formula (1) are preferably used as component A) where R is hydrogen or an optionally substituted alkyl or aryl radical, Q is an optionally substituted alkylene, cycloalkylene or arylene radical and n is 0, 1, 2 or 3.
  • the benzene rings A and B can also be substituted independently of one another.
  • R denotes an optionally substituted alkyl radical
  • the cyclohexyl radical can also be used, which may also be substituted, for example by C 1 -C 4 alkyl or C 1 -C 4 alkoxy.
  • R is an optionally substituted aryl radical
  • a phenyl or naphthyl radical is particularly suitable, which can be substituted by C 1 -C 4 -alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert.
  • Q is an alkylene radical, it is primarily a C 2 -C 4 alkylene radical, in particular a -CH 2 -CH 2 bridge.
  • a C 2 -C 8 alkylene chain interrupted by oxygen or, in particular, nitrogen is also suitable, in particular the - (CH 2 ) 3 -NH- (CH 2 ) 3 bridge.
  • Q is an arylene radical, it is primarily a phenylene radical, in particular an o-phenylene radical. This can also be substituted by C I -C 4 alkyl or C I -C 4 alkoxy.
  • Q is a cycloalkylene radical, it is a cycloaliphatic radical with 5-7 C atoms, such as cyclopentylene, cyclohexylene or cycloheptylene.
  • Possible substituents for the benzene rings A and B are: halogen, such as fluorine, chlorine or bromine, the cyano or nitro group, alkyl, alkoxy, hydroxy, hydroxyalkyl, alkoxyalkoxy, alkoxyalkoxyalkoxy, carboxymethoxy, alkylamino, dialkylamino, -SO 2 NH 2 , -SOzNHR or -SO 2 N (R o ) 2 , where R is alkyl or alkoxyalkyl and where under Alkyl and alkoxy are each to be understood as residues with 1-4 C atoms, or a benzene residue formed from residues ortho to one another, together with the C atoms to which they are attached.
  • halogen such as fluorine, chlorine or bromine
  • the sulfo group (s) which are located in the benzene rings A and / or B and / or in the bridge member Q, if this denotes an arylene radical, are preferably in the form of an alkali metal salt, in particular a sodium salt or else an amine salt.
  • cycloaliphatic radicals formed by X and Y together with the C atoms to which they are attached are cyclopentylene, cyclohexylene or cycloheptylene radicals.
  • Copper complexes of acylhydrazones of aromatic aldehydes and ketones as component A) are primarily the complexes of the formula (3) wherein R 1 and R 5 independently of one another represent hydrogen or an optionally substituted alkyl or aryl radical, and copper complexes of semicarbazones or thiosemicarbazones as component A) are primarily the complexes of the formula (3a) wherein R 1 has the meaning given under formula (3) and Z 2 represents oxygen or sulfur.
  • R 1 and / or R 5 in the formulas (3) and (3a) are an alkyl radical, this can be branched or unbranched and has a chain length of preferably 1 to 8, in particular 1 to 4, carbon atoms.
  • Suitable substituents are halogen, such as fluorine, chlorine or bromine, C 1 -C 4 alkoxy, such as methoxy or ethoxy, also phenyl or carboxyl, C 1 -C 4 alkoxycarbonyl, such as acetyl or hydroxy, mono- or dialkylamino.
  • R i and / or R 5 in the formulas (3) and (3a) are an optionally substituted aryl radical, a phenyl or naphthyl radical which can be substituted by C 1 -C 4 -alkyl, such as methyl, ethyl, is particularly suitable , Propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl, C 1 -C 4 -alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy and tert-butoxy, Halogen, such as fluorine, chlorine and bromine, C 2 -C 5 -alkanoylamino, such as acetylamino, propionylamino and butyrylamino, nitro, cyano, sulfo or a mono- or dialkylated amino group.
  • C 1 -C 4 -alkyl such
  • Complexes of the formula (3) are preferably used in which R 1 is hydrogen and R 5 is hydrogen, methyl or, in particular, the phenyl radical, in particular the complexes in which the sulfo group is in turn in the p-position to the oxygen.
  • the complexes of formula (1), (3) and (3a) are preferably in neutral form, i.e. used as alkali salt, in particular sodium salt or amine salt.
  • Suitable alkyl radicals are those with 1 to 4 carbon atoms.
  • Suitable cycloalkyl radicals are cyclohexyl and methylcyclohexyl radicals.
  • Suitable substituents in ring A are methyl, methoxy or chlorine. However, this ring is preferably unsubstituted.
  • Copper complexes of the formula (6) are of particular interest wherein R 10 , R 11 and R 13 each represent hydrogen, chlorine, bromine, methyl or methoxy and R 11 additionally also mean sulfo or Rio and R 11 together form a fused-on benzene ring, R 12 is hydrogen or hydroxy and X 2 is hydrogen, methyl, ethyl or Is phenyl.
  • component B all those compounds can be mentioned which are also known as UV absorbers and e.g. in Kirk-Othmer 23, 615-627; A.F. Strobel, ADR, 50, (1961), 583-588; 51 (1962) 99-104 R. Gumbleter and H. Müller, Taschenbuch der Kunststoff-Additive, Carl Hanser Verlag, Kunststoff pp. 101-198 (1983) and in US-A-4,511,596.
  • the light stabilizer can contain one or more such groups of the formula (9), for example it can be a mono-, bis-, tris-, tetra- or oligo-piperidine compound.
  • piperidine derivatives which contain one or more groups of the formula (9) in which R is hydrogen, and those whose ring nitrogen does not bear a hydrogen atom.
  • n is a number from 1 to 4, preferably 1 or 2
  • R is hydrogen or methyl
  • R 1 is hydrogen, oxyl, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 7 -C 12 aralkyl, C 1 -C 8 alkanoyl, C 3 -C S alkenoyl, glycidyl or a group -CH 2 CH (OH) -Z, where Z is hydrogen, methyl or phenyl, where R 1 is preferably Ci C12 is alkyl, allyl, benzyl, acetyl or acryloyl and R 2 , if n is 1, is hydrogen, C 1 -C 18 alkyl, cyanoethyl, benzyl, glycidyl optionally interrupted by one or more oxygen atoms, a monovalent radical of an aliphatic, cycloaliphatic,
  • any substituents are C 1 -C 12 alkyl, they represent, for example, methyl, ethyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethyl-hexyl, n-nonyl, n-decyl, n-undecyl or n-dodecyl.
  • R i or R 2 can represent, for example, the groups mentioned above and, for example, n-tridecyl, n-tetradecyl, n-hexadecyl or n-octadecyl.
  • R 1 is C 3 -Cg alkenyl, it can be, for example, 1-propenyl, allyl, methallyl, 2-butenyl, 2-pentenyl, 2-hexenyl, 2-octenyl, 4-tert-butyl-2-butenyl act.
  • R 1 as C 3 -C 8 alkynyl is preferably propargyl.
  • R 1 is especially phenethyl or especially benzyl.
  • R 1 is as C 1 -C 8 alkanoyl, for example formyl, propionyl, butyryl, octanoyl, but preferably acetyl and as C 3 -C 5 alkenoyl, in particular acryloyl.
  • R 2 is a monovalent radical of a carboxylic acid, it represents, for example, acetic, caproic, stearic, acrylic, methacrylic, benzoic or ⁇ - (3,5-di-tert-butyl-4-hydroxy) phenyl) propionic acid residue.
  • R 2 is a divalent radical of a dicarboxylic acid, it represents, for example, malonic, adipic, suberic, sebacic, maleic, phthalic, dibutylmalonic, dibenzylmalonic, butyl (3,5-di-tert.- butyl-4-hydroxybenzyl) malonic or bicycloheptenedicarboxylic acid residue.
  • R 2 represents a trivalent carboxylic acid residue, it means, for example, a trimellitic acid or a nitrilotriacetic acid residue.
  • R 2 represents a tetravalent residue of a tetracarboxylic acid, it means, for example, the tetravalent residue of butane-1,2,3,4-tetracarboxylic acid or of pyromellitic acid.
  • R 2 is a divalent radical of a dicarbamic acid, it is, for example, a hexamethylene dicarbamic acid or a 2,4-tolylene dicarbamic acid radical.
  • any substituents are C 1 -C 12 - or C 1 -C 18 alkyl, they have the meaning already given under aa).
  • any substituents are C 5 -C 7 cycloalkyl, they are in particular cyclohexyl.
  • R 3 is in particular phenylethyl or especially benzyl.
  • R 3 is in particular 2-hydroxyethyl or 2-hydroxypropyl.
  • R 3 is as C 2 -C 18 alkanoyl, for example propionyl, butyryl, octanoyl, dodecanoyl, hexadecanoyl, octadecanoyl, but preferably acetyl, and as C 3 -C 5 alkenoyl in particular acryloyl.
  • R 4 is C 2 -C 8 alkenyl, then it is, for example, allyl, methallyl, 2-butenyl, 2-pentenyl, 2-hexenyl or 2-octenyl.
  • R 4 as a C 1 -C 4 alkyl substituted by a hydroxy, cyano, alkoxycarbonyl or carbamide group can, for example, 2-hydroxyethyl, 2-hydroxypropyl, 2-cyanoethyl, methoxycarbonylmethyl, 2-ethoxycarbonylethyl, 2-aminocarbonylpropyl or 2- ( Be dimethylaminocarbonyl) ethyl.
  • Any C 2 -C 12 alkylene substituents are, for example, ethylene, propylene, 2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
  • Any C 6 -C 15 arylene substituents are, for example, o-, m- or p-phenylene, 1,4-naphthylene or 4,4'-diphenylene.
  • D is in particular cyclohexylene.
  • Suitable component C) are sterically hindered phenols, for example hydroxiphenylpropionates of the formula (13) wherein n is an integer from 1 to 4 and AC 1 -C 24 alkoxy, a bridge member -O (CH 2 ) 6 O-, -O (CH 2 ) 2 O (CH 2 ) 2 O-, -O (CH 2 ) 2 O (CH 2 ) 2 O (CH 2 ) 2 O-, -HN- (CH 2 ) 2-6- NH- or -O (CH 2 ) 2 -S- (CH 2 ) 2 O-or the remainder are - (CH 2 O) 4 -C, such as the esters of 3- (3 ', 5'-di-tert-butyl-4-hydroxyphenyl) propionic acid with methanol, octadecanol, 1,6-hexanediol, Diethylene glycol, triethylene glycol or pentaerythritol or the diamide
  • components A), B) and C) are known and can be prepared by processes known per se.
  • the compounds of formulas (1) to (6) are e.g. known from EP-A 51 188, 113 856 and 162 811 and can be prepared by known methods.
  • the compounds of the formulas (7) and (8) can be prepared by processes known per se, as described, for example, in US Pat. Nos. 3,403,183 and 4,127,586, respectively.
  • Compounds of the formula (8) in which R 1 , Rz, R 3 and / or R 4 are sulfo can be prepared by the process described in EP-A-112120.
  • the compounds of formula (12) can be prepared in a manner known per se, e.g. according to the methods described in Helv. 55, 1566-1595 (1972) and in WO 86/03528.
  • the compounds of formula (14) can be prepared in a manner known per se, e.g. following the procedures described in US-A-3,268,630.
  • the agents according to the invention are expediently applied from an aqueous bath, these being used advantageously in an amount such that 5 to 200 ⁇ g, in particular 10 to 100 ⁇ g, of copper metal are added to 1 g of polyamide. They therefore contain a) 0.005 to 0.2% by weight of an organic copper complex, b) 0.05 to 3, preferably 0.1 to 1% by weight of a light stabilizer and optionally c) 0.05 to 3, preferably 0.1 up to 1% by weight of an antioxidant.
  • the agents according to the invention which are also the subject of the present invention, are used for stabilizing colored material before, during or after dyeing.
  • the agent is expediently added directly to the dyebath.
  • the coloring is carried out continuously or discontinuously.
  • the agents according to the invention are expediently used as finely divided dispersions which are obtained by grinding in the presence of customary dispersants.
  • Polyamide material is understood to mean synthetic polyamide, such as polyamide-6, polyamide-6,6 or also polyamide-12.
  • fiber mixtures made of polyurethane and polyamide are also considered, for example tricot material made of polyamide / polyurethane in a mixing ratio of 70:30.
  • the pure or mixed polyamide material can be in a wide variety of processing forms, such as fiber, yarn, woven or knitted fabric.
  • Mainly polyamide material that is exposed to light and heat e.g. As a car upholstery fabric or carpets, it is particularly suitable for being treated by the present method.
  • the coloring takes place in the usual way e.g. with metal complex, anthraquinone or azo dyes.
  • metal complex anthraquinone or azo dyes.
  • the known types in particular the 1: 2 chromium or 1: 2 cobalt complexes of mono- or disazo or -azomethine dyes, which are described in large numbers in the literature, are used as metal complex dyes.
  • dyes from other dye classes are of course also possible, such as Disperse or vat dyes.
  • Example 1 Improvement of the photo stability and the light fastness of an olive color.
  • the compounds are added to the dye bath in dissolved form.
  • Dyeing liquor 1 no further additives.
  • Dyeing liquor 2 0.04% of the copper complex of the formula in finely dispersed form (particle size ⁇ 2 ⁇ m); ground with the condensation product of naphthalenesulfonic acid and formaldehyde as a dispersant in a weight ratio of 1: 1; aqueous dispersion
  • Dyeing liquor 3 1% of the light stabilizer of the formula in finely dispersed form (particle size ⁇ 2 ⁇ m); ground with the condensation product of naphthalenesulfonic acid and formaldehyde as a dispersant in a weight ratio of 1: 1.
  • Dyeing liquor 4 the additives of dyeing liquors 2 and 3 combined.
  • the dyeing materials are added to the liquors prepared as described, treated at 40 ° C for 5 minutes and heated at a rate of 1.5 ° C / min. to 95 ° C. The mixture is left at this temperature for 60 minutes, the dye bath is then cooled to 70 ° C., the dyeings are rinsed in cold water, centrifuged and dried at 80 ° C. in a forced air oven.
  • the polyamide staple yarn is wound up on cardboard and exposed for 750 hours under xenon light or 120 hours under fractal light conditions. Then the yarn is processed according to SNV (welding Certain standards association) -standard 197.461 tested for its tensile strength and elongation. The following results are obtained, the tensile strength and elongation of unexposed and untreated polyamide 66 staple yarn being set equal to 100%.
  • Example 2 Improvement of the photo stability and the light fastness of a beige color.
  • the dyeing is carried out as described in Example 1, with the difference that the following dye combination is used for dyeing 0.04%
  • Dyeing liquor 5 only dyes 3, 4 and 5
  • Dyeing liquor 7 additionally light stabilizers of the formula (101)
  • Dyeing liquor 8 additionally a combination of the compounds of the formulas (100) and (101).
  • Example 3 Photo stabilization and light fastness improvement of a "mouse gray” staining.
  • the dye liquor 9 contains no further additive.
  • Fleets 10 and 12 also contain 0.075% of the copper complex of the formula used, while the dye liquors 11 and 12 still contain 1% of the light stabilizer of the formula (101).
  • Example 4 Improvement of the photo stability and the light fastness of a gray color.
  • skeins of polyamide 66 staple yarn are each dyed gray in a dyeing machine as described in Examples 1 and 3. After the dyeings have been rinsed, the skeins of yarn are each treated with one of the following liquors at 60 ° C. for 45 minutes at a liquor ratio of 1:20 with the addition of 2% acetic acid (80%).
  • the compounds of the formulas (400) and (401) are ground in aqueous solution of the condensation product of naphthalenesulfonic acid and formaldehyde as a dispersant in a weight ratio of 1: 1 to a particle size of ⁇ 2 ⁇ m.
  • the lightfastness of the dyeings obtained with fleets 2 and 3 is the same, but is 0.5 points (xenon light) and 2 points (fractal light) better than dyeing 1.
  • the photochemical resistance after a 1000-hour exposure in xenon light shows that with Fleet 3 treated skein has a 20% better tear strength than Fleet 2 treated skein, which still has 50% of the initial strength.
  • the strand of yarn treated with the liquor 1 has only 20% of the initial strength.
  • the 12 yarn strands are dyed as described in Example 1, with the difference that 2% acetic acid (80%) is added to the dyebath at 95 ° C. after a dyeing time of 20 minutes.
  • the Cu complex primarily improves fiber stability and fakra light fastness, while the UV absorber helps to improve light fastness according to xenon and especially Ford (high UV radiation).
  • the thick crystal sludge is then heated again to 80 ° C., resulting in a well-filable crystal form, and filtered off after cooling at room temperature. It is dried at 100 ° C. in vacuo. Yield: 83.5 g.
  • the product can be recrystallized from ethanol / water in a ratio of 8: 2.
  • Example 6 10 pieces of 10 g of a highly matted polyamide 6 tricot material are dyed with the olive dye mixture of Example 1 as indicated there, the dyebaths containing the following additives and at 95 ° C. after 20 minutes of dyeing time 2% acetic acid (80%) be added.
  • the lightfastnesses of the dyeings are determined according to DIN 75.202 prov. (Fakra). They are summarized in the following table:
  • Example 7 5 skeins of 10 g of a polyamide 6 carpet yarn are in a dyeing machine at a liquor ratio of 1:30 with 1% acetic acid (80%) and 1%, based on the weight of the goods, of dye 8 of the formula dyed by entering at 50 ° C, treated for 5 minutes at this temperature, then heated to 85 ° C within 20 minutes, 1% acetic acid (80%) added, dyed for 30 minutes, cooled, the dyeing rinsed in cold water and dries, the liquors also contain the following additives
  • the dyed yarn is tested for its light fastness (xenon light, fakra), exposed 100 h after fakra and 1000 h after xenon and tested for its tear strength and elongation.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Artificial Filaments (AREA)
EP87810272A 1986-05-05 1987-04-29 Procédé de stabilisation photochimique de matière fibreuse en polyamide teinté ou non teinté et ses mélanges avec d'autres fibres Expired - Lifetime EP0245204B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT87810272T ATE92552T1 (de) 1986-05-05 1987-04-29 Verfahren zur fotochemischen stabilisierung von ungefaerbtem und gefaerbtem polyamidfasermaterial und dessen mischungen mit anderen fasern.

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CH182686 1986-05-05
CH1826/86 1986-05-05
CH5057/86 1986-12-18
CH505786 1986-12-18

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KR (1) KR940011787B1 (fr)
AU (1) AU599649B2 (fr)
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DE (1) DE3786829D1 (fr)
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EP0280653A1 (fr) * 1987-02-27 1988-08-31 Ciba-Geigy Ag Procédé d'amélioration de la stabilité photochimique de teintures sur des matières fibreuses en polyester
EP0354174A1 (fr) * 1988-07-01 1990-02-07 Ciba-Geigy Ag Composition aqueuse, stable, apte à modifier la stabilité à la lumière
EP0362139A1 (fr) * 1988-09-29 1990-04-04 Ciba-Geigy Ag Procédé de stabilisation photochimique de matière fibreuse teinte et non teinte en polyamide et ses mélanges
GB2229740A (en) * 1989-02-22 1990-10-03 Sandoz Products Ltd Dyeing polyamide fibre and treatment with oxanilide and copper compound
EP0413146A1 (fr) * 1989-07-29 1991-02-20 Bayer Ag Préparation sèche d'un mélange pour améliorer la résistance à la lumière
EP0417040A1 (fr) * 1989-09-06 1991-03-13 Ciba-Geigy Ag Procédé pour teindre la laine
EP0436470A1 (fr) * 1990-01-03 1991-07-10 Ciba-Geigy Ag Procédé pour la stabilisation photochimique de matériaux teints fibreux de polyamides
EP0475905A1 (fr) * 1990-09-13 1992-03-18 Ciba-Geigy Ag Procédé pour stabiliser photochimiquement la laine
EP0512946A1 (fr) * 1991-05-02 1992-11-11 Ciba-Geigy Ag Procédé pour améliorer la solidité à la lumière du cuir
EP0523006A1 (fr) * 1991-07-12 1993-01-13 Ciba-Geigy Ag Procédé d'impression et de stabilisation photochimique de matériaux fibreux en polyester
FR2717809A1 (fr) * 1994-03-24 1995-09-29 Sandoz Sa Dérivés de la s-triazine, leur préparation et leur utilisation comme absorbeurs UV.
EP0774539A3 (fr) * 1995-11-03 1997-08-27 Boehme Filatex Inc Composition absorbant les rayons UV et procédé pour améliorer le solidités lumière des textiles teints

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Cited By (19)

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Publication number Priority date Publication date Assignee Title
EP0280653A1 (fr) * 1987-02-27 1988-08-31 Ciba-Geigy Ag Procédé d'amélioration de la stabilité photochimique de teintures sur des matières fibreuses en polyester
EP0354174A1 (fr) * 1988-07-01 1990-02-07 Ciba-Geigy Ag Composition aqueuse, stable, apte à modifier la stabilité à la lumière
EP0362139A1 (fr) * 1988-09-29 1990-04-04 Ciba-Geigy Ag Procédé de stabilisation photochimique de matière fibreuse teinte et non teinte en polyamide et ses mélanges
GB2229740B (en) * 1989-02-22 1993-01-13 Sandoz Products Ltd Process for treating polyamide
GB2229740A (en) * 1989-02-22 1990-10-03 Sandoz Products Ltd Dyeing polyamide fibre and treatment with oxanilide and copper compound
EP0413146A1 (fr) * 1989-07-29 1991-02-20 Bayer Ag Préparation sèche d'un mélange pour améliorer la résistance à la lumière
EP0417040A1 (fr) * 1989-09-06 1991-03-13 Ciba-Geigy Ag Procédé pour teindre la laine
EP0436470A1 (fr) * 1990-01-03 1991-07-10 Ciba-Geigy Ag Procédé pour la stabilisation photochimique de matériaux teints fibreux de polyamides
EP0475905A1 (fr) * 1990-09-13 1992-03-18 Ciba-Geigy Ag Procédé pour stabiliser photochimiquement la laine
EP0512946A1 (fr) * 1991-05-02 1992-11-11 Ciba-Geigy Ag Procédé pour améliorer la solidité à la lumière du cuir
EP0523006A1 (fr) * 1991-07-12 1993-01-13 Ciba-Geigy Ag Procédé d'impression et de stabilisation photochimique de matériaux fibreux en polyester
FR2717809A1 (fr) * 1994-03-24 1995-09-29 Sandoz Sa Dérivés de la s-triazine, leur préparation et leur utilisation comme absorbeurs UV.
BE1009558A5 (fr) * 1994-03-24 1997-05-06 Clariant Finance Bvi Ltd Derives de la s-triazine, leur preparation et leur utilisation comme absorbeurs uv.
ES2101645A1 (es) * 1994-03-24 1997-07-01 Sandoz Ag Compuestos de la serie s-triazinica.
US5760227A (en) * 1994-03-24 1998-06-02 Clariant Finance (Bvi) Limited Compounds of the s-triazine series
CH689479GA3 (de) * 1994-03-24 1999-05-14 Clariant Finance Bvi Ltd Verbindungen der s-Triazinreihe.
US5998306A (en) * 1994-03-24 1999-12-07 Clariant Finance (Bvi) Limited Methods of finishing textile materials
EP0774539A3 (fr) * 1995-11-03 1997-08-27 Boehme Filatex Inc Composition absorbant les rayons UV et procédé pour améliorer le solidités lumière des textiles teints
US6391065B1 (en) 1995-11-03 2002-05-21 Boehme Filatex, Inc. UV light absorber composition and method of improving the lightfastness of dyed textiles

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AU599649B2 (en) 1990-07-26
KR870011320A (ko) 1987-12-22
EP0245204B1 (fr) 1993-08-04
US4775386A (en) 1988-10-04
BR8702227A (pt) 1988-02-17
ES2058136T3 (es) 1994-11-01
AU7247287A (en) 1987-11-12
NZ220187A (en) 1990-01-29
DE3786829D1 (de) 1993-09-09
KR940011787B1 (ko) 1994-12-26

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