EP0438381B1 - Stabilisation de la teinture sur des fibres polyamides - Google Patents

Stabilisation de la teinture sur des fibres polyamides Download PDF

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Publication number
EP0438381B1
EP0438381B1 EP91810014A EP91810014A EP0438381B1 EP 0438381 B1 EP0438381 B1 EP 0438381B1 EP 91810014 A EP91810014 A EP 91810014A EP 91810014 A EP91810014 A EP 91810014A EP 0438381 B1 EP0438381 B1 EP 0438381B1
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Prior art keywords
amino
formula
radical
use according
methyl
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EP91810014A
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German (de)
English (en)
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EP0438381A1 (fr
Inventor
Gerhard Dr. Reinert
Francesco Dr. Fuso
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BASF Schweiz AG
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Ciba Geigy AG
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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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • D06M13/244—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
    • 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
    • D06M13/415—Amides of aromatic carboxylic acids; Acylated aromatic amines
    • 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
    • D06P1/62—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
    • D06P1/628—Compounds containing nitrogen
    • 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
    • D06P1/96—Dyeing characterised by a short bath ratio
    • 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

  • Dyes on polyamide fibers which are dyed with disperse, acid or 1: 2 metal complex dyes tend to be thermally and / or photochemically unstable. This is particularly pronounced in the case of polyamide fibers which are colored with a red dye or with a dye mixture containing at least one red component.
  • 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. Preferred are a-branched alkyl groups. 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 a-methyl and a, a-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. At least one m- Position on the hydroxyl group is unsubstituted, while the other may be substituted by lower alkyl groups, such as the methyl group.
  • 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-thiatrimethylene 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 include the ß-hydroxyethyl, ß-methoxyethyl, ß-aminoethyl, ⁇ , ⁇ '-diethylamino-ethyl or the ⁇ -butylaminoethyl 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 , C1-C4-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 alkox ycarbonylamino 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, C1-C4 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
  • C1-C4 Alkoxy groups such as the methoxy group
  • acylamino groups such as the acetyl or benzoylamino group
  • alkoxycarbonylamino groups such as the methoxy or ethoxycarbonylamino
  • the group Z can optionally be substituted by C1-C4-alkyl or alkoxy groups, such as the methyl or methoxy group.
  • the sulfo group W in formula (1) is preferably free, but can also be present in the form of its alkali metal or 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 is present as the ammonium salt of an organic nitrogen base, the cation of the formula (6)
  • 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.
  • Examples of starting products of formula (11) falling under formula (8) 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-butyl-phenyl-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-cyclohex
  • the compounds of formula (1) are applied from an aqueous bath which contains the compounds in an amount of 0.01 to 10, preferably 0.25 to 3% by weight.
  • the water-soluble phenolic antioxidant can be applied during or after dyeing, using an exhaust or continuous process. Application during dyeing is preferred.
  • the liquor ratio can be selected within a wide range, for example 1: 3 to 1: 100, preferably 1:10 to 1:40. It is convenient to work at a temperature of 30 to 130 ° C, preferably 50 to 95 ° 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.
  • 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.
  • azo, 1,2-metal complex dyes e.g. 1: 2 chromium, 1: 2 cobalt complex dyes or Cu complex dyes are generated.
  • colorations which are produced by red dyes or by dye mixtures having a red component.
  • Synthetic polyamide e.g. Polyamide-6, polyamide-6,6 or polyamide-12, as well as modified polyamide, e.g. understood basic dyeable polyamide.
  • fiber mixtures made of polyurethane and polyamide are also considered, e.g. Jersey 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, e.g. as fiber, yarn, fabric, knitted fabric, fleece or pile material.
  • the use according to the invention is particularly suitable for dyeings on polyamide material which is exposed to light and / or heat and e.g. is available as carpets or upholstery.
  • the use is also suitable for the thermal stabilization of colored polyamide material provided for the so-called "molding" process.
  • This process is a shaping process that works briefly at high temperatures (e.g. bra production).
  • Example 1 2 samples of 10 g each of a PA-6 knitted fabric are dyed, for example in an @AHIBA dyeing machine at a liquor ratio of 1:30.
  • the liquor (1) receives no further addition, the liquor (2), however, 1% of the compound of the formula Dyeing begins at 30 ° C., the mixture is held at this temperature for 10 minutes and heated at 2 ° / min to 95 ° C. After a dyeing time of 20 minutes at 95 ° C, 2% acetic acid (80%) is added and dyeing is continued for 20 minutes. The mixture is then cooled to 50 ° C., rinsed, centrifuged and the samples are dried.
  • the dyeings are tested for lightfastness according to SN-ISO 105-B02 (xenon) and DIN 75202 (Fakra) as well as in a heat test at 130 ° C for 60 hours in a convection oven for color stability.
  • compound (101) imparts both photochemical and thermal protection to the stain.
  • EXAMPLE 2 The procedure is as described in Example 1, but 0.4% of the dye of the formula is used instead of the dye (100) a.
  • the compound (101) primarily gives the dyeing thermal protection.
  • Example 4 2 samples of 10 g each of a PA-6 knitwear are dyed beige, for example in an @AHIBA dyeing machine at a liquor ratio of 1:30.
  • the liquor (1) receives no further addition, the liquor (2), however, 1% of the compound of the formula
  • the examination of the colors gave the following result:
  • Example 5 Five samples of 10 g each of a PA-6 knitted fabric are separated, each with the following dye combination of 0.002% of the dye of the formula (300) given in Example 3 and 0.04% of the dye mixture (402) (403) , and from 81 parts of the dye of the formula and 12 parts of the dye of the formula as noted in Example 1, colored.
  • Dye bath 1 contains no further additives, while baths 2-6 each contain 1% of the compounds of formulas (502) - (506) in dissolved form.
  • the dyeings are tested for their light fastness according to DIN 75.202 (FAKRA), for their loss of mechanical properties (test according to SN 198.461) and for their heat resistance. The following results resulted:
  • Example 6 Two samples of a PA66 jersey are colored violet as described in Example 1 with the following amounts of dye: 0.15% of the dye of the formula (100) given in Example 1 and 0.075% of the dye of the formula given in Example 4 (401 ).
  • the dye bath 1 contains no further additive, while the dye bath 2 additionally contains 1.5% of the compound of the formula (402) given in Example 4.
  • the well-rinsed and dried tricot material is then subjected to a heat treatment under so-called “molding” conditions ("molding” means a heat deformation process, such as is used in the manufacture of bras).
  • molding means a heat deformation process, such as is used in the manufacture of bras.
  • the material is heated in a controlled manner on a "System BASF" precision ironing press (manufacturer K. Schröder KG, D-Weinheim / Bergstr.).
  • System BASF precision ironing press

Claims (13)

1. Utilisation d'un composé de formule
Figure imgb0067
dans laquelle
A est le résidu d'un phénol à encombrement stérique important de la série benzénique,
Y représente un résidu de formule (2) ou (3)
Figure imgb0068
Figure imgb0069
dans lesquelles X et X' représentent indépendamment un groupe alkylène, oxa-alkylène ou thia- alkylène,
R2 et R3 représentent indépendamment l'un de l'autre un atome d'hydrogène ou un groupe alkyle pouvant être substitué et
x, x' et y sont indépendamment l'un de l'autre égaux à 0 ou 1,
Z représente un résidu aliphatique ou un résidu aromatique carbocyclique, ce dernier pouvant contenir au plus deux noyaux mono- ou bicycliques,
W représente un groupe sulfo et
m et n valent indépendamment l'un de l'autre 1 ou 2, et leur sels hydrosolubles pour améliorer la stabilité thermique et/ou photochimique de teintures sur des fibres en polyamide.
2. Utilisation conforme à la revendication 1, caractérisée en ce que l'on utilise un composé de formule (1), dans lequel A représente un résidu mono-hydroxyphényle, dans lequel au moins une position en ortho par rapport au groupe hydroxyle est substituée par un groupe alkyle en C1-12, cycloalkyle en C6-, ou aralkyle en C7 -10 et qui porte éventuellement encore d'autres substituants.
3. Utilisation conforme à une des revendications 1 et 2, caractérisée en ce que l'on utilise un composé de formule (1) dans lequel A représente un résidu de formule (4)
Figure imgb0070
dans laquelle
R et R1 représentent indépendamment l'un de l'autre un atome d'hydrogène, un groupe méthyle ou ter-butyle et la somme des atomes de carbone de R et R1 est au moins égale à 2.
4. Utilisation conforme à une des revendications 1 à 3 dans laquelle, dans les composé de formule (2) et (3), X et X' représentent un groupe alkylène à chaîne linéaire ou ramifiée comportant de 1 à 8 atomes de carbone.
5. Utilisation conforme à une des revendications 1 à 4 dans laquelle, dans les formule (2) et (3), R2 et R3 représentent un groupe alkyle à chaîne linéaire ou ramifiée comportant de 1 à 8 atomes de carbone.
6. Utilisation conforme à une des revendications 1 à 4 dans laquelle, dans les formule (2) et (3), R2 et R3 représente un groupe hydroxyle, alcoxyalkyle, aminoalkyle, alkylaminoalkyle ou dialkylaminoalkyle comportant cnacun en tout de 2 - 10 atomes de carbone ou un résidu phényle.
7. Utilisation conforme à la revendication 1 dans laquelle, dans la formule (1), Y représente un résidu de formule (5)
Figure imgb0071
dans laquelle R4 représente un atome d'hydrogène ou un groupe alkyle en Ci -4 et X" représente un groupe alkylène en C, -4.
8. Utilisation conforme à une des revendications 1 à 7, caractérisée en ce que Z dans la formule (1) représente le résidu d'un alcane comportant au moins deux atomes de carbone et qui est non substitué ou porte un ou plusieurs groupes carboxyle, le résidu d'un noyau benzénique non substitué ou substitué par un résidu chloro, bromo, alkyle en C1-4, alcoxy en C1-4, (alcoxy en C1-4)-carbonylami- no, hydroxy, carboxy, phényléthyle, styryle, phényle, phénoxy, phénylthio, phénylsulfonyle ou acylamino, le groupe W pouvant être lié directement à ce noyau benzénique ou à un résidu aryle monocyclique d'un de ses substituants, ou il représente un résidu naphtalène ou tétraline.
9. Utilisation conforme à la revendication 1, caractérisée en ce que l'on utilise un composé de formule (7)
Figure imgb0072
dans laquelle
R et R1 représentent indépendamment l'un de l'autre un groupe méthyle ou ter-butyle,
R4 représente un atome d'hydrogène ou un groupe alkyle en C1-4,
X" représente un groupe alkylène en C1-4,
Z représente un résidu éthylène, un résidu divalent ou trivalent de benzène ou de naphtalène ou un résidu divalent d'un résidu éther de diphényle,
W représente un groupe sulfo et n est égal à 1 ou 2.
10. Utilisation conforme à la revendication 9, caractérisée en ce que l'on utilise des composés de formule (7) dans lesquels R et R1 représentent un résidu t-butyle, X" représente un groupe méthylène ou éthylène, R4 représente un atome d'hydrogène, un groupe méthyle ou éthyle et Z un groupe éthylène, o-, m- ou p-phénylène, 1,4-naphtylène, 1,8-naphtylène, 2-méthoxy-1,6-naphtylène, 1,5-naphtylène, 2,5-naphtylène, 2,6-naphtylène, 1,4,6-naphtalènentriyl ou les résidus
Figure imgb0073
Figure imgb0074
Figure imgb0075
Figure imgb0076
où le groupe sulfo W peut se trouver également sous forme de sel de métal alcalin ou de sel d'ammonium.
11. Utilisation conforme à une des revendications 1 à 10, caractérisée en ce que le composé de formule (1) est appliqué aux fibres selon un procédé par épuisement ou en continu.
12. Utilisation conforme à une des revendications 1 à 11 pour l'amélioration de la stabilité thermique et/ou photochimique de fibres de polyamide teintes avec des colorants acides ou métallifères.
13. Utilisation conforme à la revendication 12 pour améliorer la stabilité thermique et/ou photochimique de fibres en polyamide teintes avec des colorants acides rouges ou des complexes colorant-métal de stoechiométrie 2:1 rouges ou avec un mélange de colorants contenant un composant rouge.
EP91810014A 1990-01-19 1991-01-10 Stabilisation de la teinture sur des fibres polyamides Expired - Lifetime EP0438381B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH173/90 1990-01-19
CH17390 1990-01-19

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EP0438381A1 EP0438381A1 (fr) 1991-07-24
EP0438381B1 true EP0438381B1 (fr) 1995-04-05

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JP (1) JP3051461B2 (fr)
CA (1) CA2034393C (fr)
DE (1) DE59105066D1 (fr)

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DE59105066D1 (de) 1995-05-11
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CA2034393A1 (fr) 1991-07-20
CA2034393C (fr) 2002-01-08
US5096456A (en) 1992-03-17
EP0438381A1 (fr) 1991-07-24

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