EP0459950B1 - Stabilisation de teintures sur des fibres en polyamides - Google Patents

Stabilisation de teintures sur des fibres en polyamides Download PDF

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Publication number
EP0459950B1
EP0459950B1 EP91810388A EP91810388A EP0459950B1 EP 0459950 B1 EP0459950 B1 EP 0459950B1 EP 91810388 A EP91810388 A EP 91810388A EP 91810388 A EP91810388 A EP 91810388A EP 0459950 B1 EP0459950 B1 EP 0459950B1
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Prior art keywords
alkyl
formula
radical
hydrogen
process according
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German (de)
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EP0459950A1 (fr
Inventor
Gerhard Dr. Reinert
Francesco Dr. Fuso
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BASF Schweiz AG
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Ciba Geigy AG
Ciba Spezialitaetenchemie Holding AG
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Classifications

    • 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
    • D06M13/322—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
    • D06M13/325—Amines
    • D06M13/342—Amino-carboxylic acids; Betaines; Aminosulfonic acids; Sulfo-betaines
    • 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
    • D06M13/322—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
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • 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 method for improving the thermal and / or photochemical stability of the dyeings on the polyamide fibers and the polyamide fiber material dyed by this method.
  • EP-A-0 255 481 discloses a process for the photochemical stabilization of polyamide fiber materials with the aid of water-soluble copper complex compounds.
  • a in formula (1) means, for example, a monohydroxyphenyl radical in which at least one o-position to the hydroxyl group is substituted by an alkyl, cycloalkyl or aralkyl group and which optionally also carries further substituents.
  • Alkyl groups in the o-position to the hydroxyl group of A can be straight or branched and contain 1-12, preferably 4-8 C atoms.
  • Alpha-branched alkyl groups are preferred. These are, for example, the methyl, ethyl, iso-propyl, tert-butyl, iso-amyl, octyl, tert-octyl and dodecyl group.
  • the tert-butyl group is particularly preferred.
  • Cycloalkyl groups in the o-position to the hydroxyl group of A contain 6-10, preferably 6-8 carbon atoms. Examples include the cyclohexyl, methylcyclohexyl and cyclooctyl group.
  • Aralkyl groups in the o-position to the hydroxyl group of A contain 7-10, preferably 8-9 carbon atoms. Examples include the ⁇ -methyl and ⁇ , ⁇ -dimethylbenzyl groups.
  • the radical A can also be substituted by further alkyl, cycloalkyl or aralkyl groups, as defined above, these preferably being in the o'- or p-position to the hydroxyl group, provided that these positions are not occupied by the bond to Y. are. Furthermore, at least one m position to the hydroxyl group is advantageously unsubstituted, while the other can be substituted by lower alkyl groups, such as the methyl group.
  • compounds of the formula (1) in which A is a radical of the formula (4) are particularly preferred in the R and R 1 independently represent hydrogen, methyl or tert-butyl and the sum of the carbon atoms of R and R 1 is at least 2.
  • X and X 'in formulas (2) and (3) can be straight-chain or branched and contain 1 to 8, preferably 1 to 5, carbon atoms. Examples of these are the methylene, ethylene, trimethylene, propylene, 2-thia-trimethylene or the 2-oxapentamethylene radical.
  • R 2 or R 3 in formulas (2) and (3) can be straight-chain or branched as an alkyl group and contain 1 to 18, preferably 1 to 8, carbon atoms. Examples include the methyl, ethyl, iso-propyl, pentyl, octyl, dodecyl and octadecyl group.
  • the substituted alkyl group R 2 or R 3 is, for example, a hydroxyalkyl, alkoxyalkyl, aminoalkyl, alkylaminoalkyl or a dialkylaminoalkyl group with a total of 2 to 10, preferably 2 to 5, carbon atoms.
  • Examples of this are the ⁇ -hydroxyethyl, ⁇ -methoxyethyl, ⁇ -aminoethyl, ⁇ , ⁇ '-diethylaminoethyl or the ⁇ -butylaminoethyl group.
  • R 2 or R 3 can also represent an aryl group, preferably the phenyl group.
  • Z in formula (1) means, for example, the residue of an unsubstituted or substituted by carboxyl groups lower alkane having at least two carbon atoms, the residue of an unsubstituted or by chlorine or bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy , C 1 -C 4 alkoxycarbonylamino, hydroxy, carboxy, phenylethyl, styryl, phenyl, phenoxy, phenylthio, phenylsulfonyl or acylamino substituted benzene nucleus, where the group W can be bonded directly to this benzene nucleus or to a monocyclic aryl radical of one of its substituents, or it means the naphthalene or tetralin residue.
  • Z can be straight-chain or branched and contain 2 to 5, preferably 2, carbon atoms. It is, for example, the ethylene, propylene, trimethylene or pentamethylene radical. This residue can optionally be substituted by carboxyl groups. An example of this is the carboxyethylene residue.
  • Z in formula (1) can be further substituted.
  • it may have straight-chain or branched C 1 -C 4 -alkyl radicals, for example substituted by the methyl, ethyl or isopropyl group; the methyl group is preferred.
  • C 1 -C 4 alkoxy groups as substituents of a benzene radical Z are, for example, the methoxy, ethoxy or butoxy group. If Z is substituted as a benzene radical by an acylamino group, its acyl radical is derived in particular from a C 2 -C 6 -aliphatic or a monocarbocyclic aromatic carboxylic acid.
  • Examples are the rest of the acetic, propionic, ⁇ -methoxypropionic, benzoic, aminobenzoic or methylbenzoic acid.
  • Examples of C 1 -C 4 alkoxycarbonylamino groups as substituents of a benzene radical Z are the methoxy, ethoxy or butoxycarbonylamino radical.
  • group Z contains phenylethyl, styryl, phenyl, phenoxy, phenylthio or phenylsulfonyl groups as substituents, these can optionally be substituted by chlorine or bromine, C 1 -C 4 -alkyl groups, such as the methyl or ethyl group, C 1 - C 4 alkoxy groups, such as the methoxy group, acylamino groups, such as the acetyl or benzoylamino group, or alkoxycarbonylamino groups, such as the methoxy or ethoxycarbonylamino group.
  • C 1 -C 4 -alkyl groups such as the methyl or ethyl group
  • C 1 - C 4 alkoxy groups such as the methoxy group
  • acylamino groups such as the acetyl or benzoylamino group
  • alkoxycarbonylamino groups such as the methoxy or ethoxycarbonyla
  • the group Z can optionally be substituted by C 1 -C 4 -alkyl or alkoxy groups, such as the methyl or methoxy group.
  • Z is the ethylene radical, a phenylene, tolylene, chlorophenylene or naphthylene radical or a divalent radical of the diphenyl ether, a methyl or a chlorodiphenyl ether, or in certain applications compounds in which Z is a trivalent radical are particularly preferred Rest of the benzene or naphthalene means.
  • Compounds in which Z represents a phenyl or diphenyl ether radical show particularly good lightfastness, while compounds in which Z represents a naphthyl or phenylethylphenyl radical have excellent wash fastness properties.
  • the sulfo group W in formula (1) is free, but can also preferably be present in the form of its alkali metal salts, alkaline earth metal salts, the ammonium salt or the salts of organic nitrogen bases. Because of the poor solubility of certain calcium, strontium and barium salts in aqueous media and for economic reasons, preference is given to compounds of the formula (1) in which the group W is in the form of its lithium, sodium, potassium, magnesium or ammonium salt or as the ammonium salt one organic nitrogen base is present, the cation of the formula (6) (6) N + R'R "R"'R"" corresponds to what R ', R ", R"', R "" independently of one another are hydrogen, a C 1 -C 4 -alkyl or ⁇ -hydroxy-C 1 -C 4 -alkyl radical or a cyclohexyl radical, at least two of these radicals being together can form carbocyclic or heterocyclic ring system.
  • organic nitrogen bases which can form such ammonium salts with group W are: trimethylamine, triethylamine, triethanolamine, diethanolamine, ethanolamine, cyclohexylamine, dicyclohexylamine, hexamethyleneimine or morpholine.
  • the group W can be present in these compounds freely or in the form of the salts defined above.
  • UV absorbers can be named, for example, which e.g. in U.S.-A-2,777,828: 2,853,521; 3,259,627; 3,293,247; 3,382,183; 3,403,183; 3,423,360; 4,127,586; 4,230,867; 4,511,596 and 4,698,064.
  • UV absorbers made water-soluble are preferred. Such are e.g. in U.S.-A-4,141,903, 4,230,867, 4,698,064 and 4,770,667.
  • the carboxy and sulfo groups can be in free form or in salt form, for example as alkali metal, alkaline earth metal, ammonium or amine salts.
  • A- (X) x -NH-R 3 wherein A, X, x and R 3 have the meaning given above are: 4-hydroxy-3,5-di-tert-butyl-aniline, 4-hydroxy-3,5-di-tert-butyl-benzylamine, ⁇ - (4-hydroxy-3,5-di-tert-butyl-phenyl ) -propylamine, 4-hydroxy-3-tert-butyl-5-methyl-aniline, 4-hydroxy-3,5-di-cyclohexyl-aniline, 4-hydroxy-3,5-di-tert.amyl-aniline, 4-hydroxy-3,5-di-cyclohexyl-benzylamine, 4-hydroxy-3-methylcyclohexyl-5-methyl-aniline, 2-hydroxy-3- ⁇ , ⁇ -dimethylbenzyl-5-methyl-benzylamine, 4-hydroxy-
  • octyl-5-methyl-benzylamine 4-hydroxy-3,5-di-isopropyl-benzylamine, 4-hydroxy-3-tert-butyl-6-methyl-benzylamine, 4-hydroxy-3,5-di-tert. amyl-benzylamine, 2-hydroxy-3,5-dimethyl-aniline and 2-hydroxy-3-tert-butyl-5-methyl-benzylamine.
  • Examples of starting products of formula (16) falling under formula (13) wherein A, X, x, R 2 , y and V have the meaning given above are: ⁇ - (4-Hydroxy-3,5-di-tert-butyl-phenyl) -propionic acid chloride, 4-hydroxy-3,5-di-tert-butylphenyl-acetyl chloride, 4-hydroxy-3,5-di-tert.
  • butyl-benzoyl chloride 4-hydroxy-3-tert-butyl-5-methyl-phenyl-acetyl chloride, 2-hydroxy-3,5-dimethyl-benzoyl chloride, 2-hydroxy-3-tert-butyl-5-methyl-benzoyl chloride, S- (4-hydroxy-3-tert-butyl-5-methyl-benzyl) thioglycolic acid chloride, 4-hydroxy-5-tert-butylphenyl acetyl chloride, ⁇ - (4-hydroxy-3,5-di-cyclohexyl-phenyl ) -propionic acid bromide, (4-hydroxy-3,5-di-cyclohexyl-phenyl) -acetyl chloride, ⁇ - (4-hydroxy-3-benzyl-5-methyl-phenyl) -propionic acid chloride, (4-hydroxy-3-benzyl -5-methyl-phenyl) -acetyl chloride, 4-hydroxy-3,5-di-
  • Examples of starting products of the formula (17) falling under formula (14) wherein W, m, Z, X ', x', R 3 and n have the meaning given above are: 2-amino-benzenesulfonic acid, 3-amino-benzenesulfonic acid, 4-amino-benzenesulfonic acid, 5-chloro-2-amino-benzenesulfonic acid, 5-methyl-4-chloro-2-amino-benzenesulfonic acid, 2-chloro-5-amino benzenesulfonic acid, 4-chloro-3-amino-benzenesulfonic acid, 5-chloro-3-methyl-3-amino-benzenesulfonic acid, 2,5-dichloro-4-amino-benzenesulfonic acid, 3-bromo-6-amino-benzenesulfonic acid, 3, 4-dichloro-6-amino-benzenesulfonic acid, 1-amino-
  • Examples of starting products of the formula (18) falling under formula (14) wherein W, m, Z, X ', x', R 2 , y, V and n have the meaning given above are: 2-sulfo-benzoyl chloride, 3-sulfo-benzoyl chloride, 4-sulfo-benzoyl chloride, 3,5-disulfobenzoyl chloride, 3-sulfo-phthaloyl chloride, 3,4-disulfo-phthaloyl chloride, 4-sulfo-phenyl-acetyl chloride, ⁇ - (4th -Sulfo-phenyl) -propionic acid chloride, 3-sulfo-6-methyl-benzoyl chloride.
  • the compounds of the formulas (8) and (9) can be prepared by methods known per se, e.g. in US-A-3,403,183 and US-A-4,127,586, respectively.
  • the compounds of formula (10) can be prepared in a manner known per se, e.g. following the procedures described in US-A-3,259,627, 3,293,247, 3,423,360 and 4,698,064.
  • the compounds of formula (11) can be prepared by methods known per se, e.g. in US-A-3 444 164 or EP-A-165 608.
  • the agents used in the process according to the invention contain components (A) and (B) in an amount of 0.01 to 10, preferably 0.2 to 2% by weight in a weight ratio (A) :( B) of 95 : 5 to 5:95, preferably 60:40 to 40:60, always calculated on the material to be dyed.
  • the application during dyeing can be carried out using a pull-out or continuous process.
  • the liquor ratio can be within a wide range can be selected, for example 1: 3 to 1: 200, preferably 1:10 to 1:40. It is convenient to work at a temperature of 20 to 120 ° C, preferably 40 to 100 ° C.
  • the liquor order is expediently 40-700, preferably 40-500% by weight.
  • the fiber material is then subjected to a heat treatment process in order to fix the applied dyes and the antioxidants. This fixation can also be done using the cold-dwell method.
  • the heat treatment is preferably carried out by a steaming process with treatment in a steamer with possibly superheated steam at a temperature of 98 to 105 ° C during e.g. 1-7, preferably 1-5 minutes.
  • the dyes can be fixed in accordance with the cold residence process by storing the impregnated and preferably rolled-up goods at room temperature (15 to 30 ° C) e.g. during 3 to 24 hours, the cold residence time being known to depend on the dye.
  • the dyeings produced are washed and dried in the customary manner.
  • Dyed fiber materials with good thermal and / or photochemical stability are obtained according to the present invention.
  • dyeings to be stabilized according to the invention those are suitable which are disperse, acid or metal complex dyes, in particular azo, 1: 2 metal complex dyes, e.g. 1: 2 chromium, 1: 2 cobalt complex dyes or Cu complex dyes are generated.
  • Polyamide material is understood to mean synthetic polyamide, such as, for example, polyamide-6, polyamide-6,6 or polyamide-12, as well as modified polyamide, for example polyamide which can be dyed in a basic manner.
  • 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, knitted, nonwoven or pile material.
  • the liquor (1) receives no further addition, the liquor (2), however, 1% of the compound of the formula and the liquor (3) 1% of the compound (101) and additionally 1% of the compound of the formula (102), always calculated on the material to be colored.
  • Dyeing is started at 40 ° C., the mixture is held at this temperature for 10 minutes and heated to 95 ° C. in 30 minutes. After a dyeing time of 20 minutes at 95 ° C, 2% acetic acid (80%) is added to each liquor and dyeing is continued for 30 minutes. The mixture is then cooled to 70 ° C., rinsed, centrifuged and the samples are dried at 80 ° C.
  • the dyeings are tested for lightfastness according to SN-ISO 105-BO2 (Xenon) and DIN 75202 (Fakra).
  • SN-ISO 105-BO2 Xenon
  • DIN 75202 France
  • samples are exposed for 216 hours in accordance with DIN 75202 and tested for their tensile strength and elongation in accordance with SN 198.461.
  • Example 2 Three dyeings (4), (5) and (6) are prepared as described in Example 1, with the difference that the following 1: 2 metal complex dye of the formula (200) is used.
  • Example 3 2 samples of 10 g each of a PA knitted fabric are dyed, for example in a ®Zeltex-Vistracolor dyeing machine at a liquor ratio of 1:30.
  • the dye liquor 2 additionally contains 1% of the compound of the formula
  • a bomb dyeing machine for example a Labomat® (Mathis company)
  • a liquor ratio of 1:20 as described in Example 3
  • the fleet 1 contains no further additive.
  • Fleet 2 contains 1% of the compound of the formula while 31% of the compound (400) and 0.75% of the compound (102) are added to the liquor. All compounds are calculated on the weight of the carpet sample and added to the dyeing liquor in dissolved form.
  • the dyeing process is carried out as described in Example 1.
  • Example 5 Three 10 g samples of a polyamide 66 / Lycra® jersey (80:20) are dyed with 0.2% dye (100) as noted in Example 1. Fleet 1 is given no further addition. The liquor 2 is mixed with 1% of the compound (300) in dissolved form, the liquor 3 with 1% of the compound (300) and 0.75% of the compound (102).
  • Examples 6-10 6 samples of 10 g of a PA 6 jersey are dyed according to Example 3 and dyed according to the methods noted in Example 1, but with the addition of subsequent UV absorbers, finished and according to SN-ISO 105-B02 (xenon ) and DIN 75.202 (Fakra) examined for light fastness.
  • Examples 11-15 12 samples of 10 g each of a PA6 jersey are noted, dyed and tested as in Examples 6-10, but the compounds specified in the table are used in the amounts mentioned.
  • Coloring no. Coloring additive LIGHT FASTNESSES xenon Fakra 144 h Fakra 216 h 1 no addition 6-7 1 H 1 H 2nd + 0.75% connection (600) 7 2nd 1-2 3rd + 1.00% connection (400) 7 2-3 2nd 4th + 1.00% + 0.75% Verb. (400) + (600) 7 4th 3rd 5 + 1.00% connection (605) 7 2-3 1-2 6 + 1.00% + 0.75% Verb.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (15)

  1. Procédé pour améliorer la stabilité thermique et/ou photochimique des colorations sur fibres de polyamide, caractérisé en ce qu'on traite les fibres en bain aqueux, par un réactif qui contient:
    (A) un composé de formule (1)

            (1)   (A-Y-)nZ(-W)m

    dans laquelle
    A représente le radical d'un phénol à encombrement stérique de la série du benzène,
    Y représente un radical de formule (2) ou (3)
    Figure imgb0072
    Figure imgb0073
     dans lesquelles
    X et X' représentent, indépendamment l'un de l'autre, un alkylène, un oxalkylène ou un thialkylène,
    R2 et R3 représentent, indépendamment l'un de l'autre, un atome d'hydrogène ou un groupe alkyle éventuellement substitué, et
    x, x' et y représentent, indépendamment les uns des autres, O ou 1,
    Z représente un radical aliphatique ou un radical aromatique carbocyclique, ce dernier contenant au maximum deux noyaux mono- ou bicycliques,
    W représente le groupe sulfo et
    m et n représentent, indépendamment l'un de l'autre, 1 ou 2 et les sels solubles de ce composé, et
    (B) représente un absorbant des UV, et
    (C) un colorant de dispersion, acide ou à complexe métallique.
  2. Procédé selon la revendication 1, caractérisé en ce que l'on utilise, comme constituant (A), un composé de formule (1) dans laquelle A représente un radical monohydroxyphénylique, dans lequel au moins une position o par rapport au groupe hydroxyle est substituée par un alkyle ayant de 1 à 12 atomes de carbone, un cycloalkyle ayant de 6 à 10 atomes de carbone, ou un aralkyle ayant de 7 à 10 atomes de carbone, et comporte éventuellement encore d'autres substituants.
  3. Procédé selon l'une des revendications 1 et 2, caractérisé en ce que l'on utilise, comme constituant (A), un composé de formule (1) dans laquelle A représente un radical de formule (4)
    Figure imgb0074
     dans laquelle R et R1 représentent, indépendamment l'un de l'autre, un atome d'hydrogène, un radical méthyle ou tert-butyle et la somme des atomes de carbone de R et R1 est égale au moins à 2.
  4. Procédé selon l'une des revendications 1 à 3, dans lequel X et X' représentent un alkylène linéaire ou ramifié ayant de 1 à 8 atomes de carbone dans les composés de formule (2) et (3).
  5. Procédé selon l'une des revendications 1 à 4, dans lequel R2 et R3 représentent un alkyle en C1-C8, linéaire ou ramifié, dans les composés de formule (2) et (3).
  6. Procédé selon l'une des revendications 1 et 4, dans lequel R2 et R3 représentent un radical hydroxyalkyle, alcoxyalkyle, aminoalkyle, alkylaminoalkyle ou dialkylaminoalkyle, ayant chaque fois au total de 2 à 10 atomes de carbone, ou un radical phényle dans les composés de formule (2) et (3).
  7. Procédé selon la revendication 1, dans lequel, dans la formule (1), Y représente un radical de formule (5)
    Figure imgb0075
     dans laquelle
    R4 représente un atome d'hydrogène ou un alkyle en C1-C4 et
    X" représente un alkylène en C1-C4.
  8. Procédé selon l'une des revendications 1 à 7, caractérisé en ce que, dans la formule (1), Z représente le radical d'un alcane avec au moins deux atomes de carbone, non substitué ou substitué par des groupes carboxyle, le radical d'un noyau benzénique non substitué ou substitué par du chlore ou du brome, un alkyle en C1-C4, un alcoxy en C1-C4, un alcoxycarbonylamino en C1-C4, un hydroxy, un carboxy, un phényléthyle, un styryle, un phényle, un phénoxy, un phénylthio, un phénylsulfonyle ou un acylamino, où le groupe W peut être lié directement à ce noyau benzénique ou à un radical aryle monocyclique d'un de ses substituants, ou bien Z représente le radical naphtalène ou tétraline.
  9. Procédé selon la revendication 1, caractérisé en ce que l'on utilise, comme constituant (A), un composé de formule (7)
    Figure imgb0076
     dans laquelle
    R et R1 représentent indépendamment l'un de l'autre, un radical méthyle ou tert-butyle,
    R4 représente un atome d'hydrogène ou un radical alkyle en C1-C4,
    X" représente un alkylène en C1-C4,
    Z le radical éthylène, un radical bi- ou trivalent du benzène ou du naphtalène ou un radical bivalent de l'éther diphénylique,
    W représente le groupe sulfo et
    n représente 1 ou 2.
  10. Procédé selon la revendication 9, caractérisé en ce que l'on utilise, comme constituant (A), un composé de formule (7), dans laquelle R et R1 représentent un tert-butyle, X" un méthylène ou un éthylène, R4 un atome d'hydrogène ou un groupe méthyle ou éthyle, et Z un groupe éthylène, un o-, m- ou p-phénylène, un 1,4-naphtylène, un 1,8-natphtylène, un 2-méthoxy-1,6-natphylène, un 1,5-naphtylène, un 2,5-naphtylène, un 2,6-naphtylène, un 1,4,6-naphtalinetriyle ou les radicaux
    Figure imgb0077
    Figure imgb0078
    Figure imgb0079
    Figure imgb0080
     dans lesquels le groupe sulfo W se présente sous la forme de ses sels alcalins ou ammoniques.
  11. Procédé selon l'une des revendications 1 à 10 caractérisé en ce que l'on utilise, comme constituant (B), une 2-hydroxybenzophénone de formule
    Figure imgb0081
     dans laquelle
    R1 représente un atome d'hydrogène, un groupe hydroxy, alcoxy en C1-C14 ou phénoxy,
    R2 représente un atome d'hydrogène ou d'halogène, un groupe alkyle en C1-C4 ou sulfo,
    R3 représente un atome d'hydrogène ou un groupe hydroxy ou alcoxy en C1-C4 et
    R4 représente un atome d'hydrogène, ou un groupe hydroxy ou carboxy.
  12. Procédé selon l'une des revendications 1 à 10, caractérisé en ce que l'on utilise, comme constituant (B), un 2-(2'-hydroxyphényl)-benzotriazole de formule
    Figure imgb0082
     dans laquelle
    R1 représente un atome d'hydrogène ou de chlore, un groupe sulfo, alkyle en C1-C12, cycloalkyle en C5-C6, (C1-C8-alkyl)phényle, C7-C9-phénylalkyle ou C7-C9-phénylalkyle sulfoné,
    R2 représente un atome d'hydrogène ou de chlore ou un groupe alkyle en C1-C4, alcoxy en C1-C4, hydroxy ou sulfo,
    R3 représente un alkyle en C1-C12, un atome de chlore ou un groupe sulfo, alcoxy en C1-C4, phényle, (C1-C8-alkyl)phényle, C5-C6-cycloalkyle, C2-C9-alcoxycarbonyle, carboxyéthyle, C7-C9-phénylalkyle ou C7-C9-phénylalkyle sulfoné,
    R4 représente un atome d'hydrogène ou de chlore ou un groupe alkyle en C1-C4, alcoxy en C1-C4, alcoxycarbonyle en C2-C9, carboxy ou sulfo et
    R5 représente un atome d'hydrogène ou de chlore,
  13. Procédé selon l'une des revendications 1 à 10, caractérisé en ce que l'on utilise, comme constituant (B), une 2-(2'-hydroxyphényl)-s-triazine de formule
    Figure imgb0083
     dans laquelle R représente un atome d'hydrogène ou d'halogène ou un groupe alkyle en C1-C4 ou sulfo,
    R1 représente un atome d'hydrogène ou un groupe alkyle en C1-C4, alcoxy en C1-C4 ou hydroxy,
    R2 représente un atome d'hydrogène ou un groupe sulfo et R3 et R4 représentent, indépendamment l'un de l'autre, un alkyle en C1-C4, un alcoxy en C1-C4, un cycloalkyle en C5-C6, un phényle ou un phényle substitué par un alkyle en C1-C4 et/ou titi hydroxy.
  14. Procédé selon l'une des revendications 1 à 10, caractérisé en ce que l'on utilise, comme constituant (B), un composé de la s-triazine de formule
    Figure imgb0084
     dans laquelle au moins l'un de substituants R1, R2 et R3 représente un radical de formule
    Figure imgb0085
     dans laquelle A représente un alkylène en C3-C4, ou un 2-hydroxytriméthylène et M représente du sodium, du potassium, du calcium, du magnésium, de l'ammonium ou du tétra-C1-C4-alkylammonium et m représente 1 ou 2, et l'autre substituant ou les autres substituants représentent indépendamment les uns des autres, un alkyle en C1-C12, un phényle, un alkyle en C1-C12 lié au radical triazine par de l'oxygène, du soufre, un imino ou un alkylimino en C1-C11, un phényle ou un radical de formule (12).
  15. Procédé selon l'une des revendications 1 à 14, caractérisé en ce que l'on extrait l'agent des fibres selon un procédé d'extraction ou en continu.
EP91810388A 1990-05-31 1991-05-22 Stabilisation de teintures sur des fibres en polyamides Expired - Lifetime EP0459950B1 (fr)

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EP0459950A1 (fr) 1991-12-04
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US5181935A (en) 1993-01-26
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