EP1817452A1 - Method of improving thermal stability - Google Patents

Method of improving thermal stability

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Publication number
EP1817452A1
EP1817452A1 EP05811066A EP05811066A EP1817452A1 EP 1817452 A1 EP1817452 A1 EP 1817452A1 EP 05811066 A EP05811066 A EP 05811066A EP 05811066 A EP05811066 A EP 05811066A EP 1817452 A1 EP1817452 A1 EP 1817452A1
Authority
EP
European Patent Office
Prior art keywords
formula
compound
nrir
hydroxy
amino
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.)
Withdrawn
Application number
EP05811066A
Other languages
German (de)
French (fr)
Inventor
Edvard Ham
Hans-Jörg PETER
Claudius Brinkmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Huntsman Advanced Materials Switzerland GmbH
Original Assignee
Huntsman Advanced Materials Switzerland GmbH
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Filing date
Publication date
Application filed by Huntsman Advanced Materials Switzerland GmbH filed Critical Huntsman Advanced Materials Switzerland GmbH
Priority to EP05811066A priority Critical patent/EP1817452A1/en
Publication of EP1817452A1 publication Critical patent/EP1817452A1/en
Withdrawn legal-status Critical Current

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    • 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
    • D06M13/332—Di- or polyamines
    • 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
    • D06M13/435—Semicarbazides
    • 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
    • D06M13/144—Alcohols; Metal alcoholates
    • D06M13/148—Polyalcohols, e.g. glycerol or glucose
    • 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
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
    • 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
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/192—Polycarboxylic acids; Anhydrides, halides or salts thereof
    • 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
    • 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
    • D06M13/338—Organic hydrazines; Hydrazinium compounds
    • D—TEXTILES; PAPER
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    • 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
    • D06M13/422—Hydrazides
    • 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
    • D06P1/6425—Compounds containing hydrazine or azo 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
    • D06P1/64—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
    • D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino 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
    • 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
    • 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
    • D06P3/248—Polyamides; Polyurethanes using reactive dyes
    • 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
    • D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs
    • 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
    • D06P5/04—After-treatment with organic 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic compounds
    • D06P5/06—After-treatment with organic compounds containing nitrogen

Definitions

  • the present invention relates to a method of improving the thermal stability of undyed, fluorescent whitened or dyed, natural or synthetic polyamide fibre materials and to a textile auxiliary for use in that method.
  • a thermal pretreatment may lead to oxidative damage to the polyamide, which manifests itself, for example, in increased yellowing or loss of tear strength or which may have an adverse effect on dyeability.
  • oxidative damage to the polyamide
  • a thermal treatment may result in unacceptable alterations in shade.
  • the present invention relates to a method of improving the thermal stability of natural or synthetic polyamide fibre materials that are undyed, fluorescent whitened or dyed with reactive or disperse dyes, with the exception of metal complex dyes, wherein the fibre material is treated with a liquor comprising a compound of formula (1)
  • X is a divalent aliphatic or cycloaliphatic radical
  • Yi and Y 2 are each independently of the other -OH, -CO-ORi, -NRiR 2 , -CO-NH-NRiR 2 or wherein Ri and R 2 are each independently of the other hydrogen; Ci-Ci 2 alkyl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms; C 5 -C 24 - aryl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms; C 6 -C 36 aralkyl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms; or C 5 -C 24 CyClOaI kyl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms.
  • Aliphatic radicals X in formula (1) are, for example, ethylene, propylene, trimethylene, propane-1,1-diyl, tetramethylene, hexamethylene, octamethylene and decamethylene or linear or branched alkylene that is interrupted by one or more O atoms or -NH-, -N(alkyl)- or -N(alkylene-NH 2 )- groups.
  • Suitable cycloaliphatic radicals X are, for example, cyclohexane-1 ,2-diyl, cyclohexane-1 ,3- diyl and also CH / ⁇ _ CH and — / ⁇ — / ⁇ __ .
  • Ci 2 Alkyl as a radical Ri or R 2 can be, for example, methyl, ethyl, n-propyl, isopropyl, n- butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, n-octyl or n-dodecyl.
  • a C 5 -C 24 aryl group as one of the radicals Ri - R 5 is, for example, phenyl, tolyl, mesityl, isityl, naphthyl or anthryl.
  • Suitable C 6 -C 36 aralkyl groups are, for example, benzyl and 2-phenylethyl.
  • C 5 -C 24 cycloalkyl examples are cyclopentyl and cyclohexyl.
  • Y 1 and Y 2 are -NR 1 R 2 , -CO-NH-NR 1 R 2 Or -NH-CO-NH-NR 1 R 2 , wherein R 1 and R 2 is hydrogen, C r C 12 alkyl or C 5 -C 24 aryl.
  • Examples of suitable compounds of general formula (1) are the compounds of formulae (101) - (104)
  • the compounds of formula (1 ) are known and are commercially available or can be synthesised by known methods.
  • the compounds of formula (1) used in the method according to the invention are present in the liquor advantageously in an amount of from 0.1 g/l to 100 g/l, preferably from 0.5 g/l to 50 g/l and especially from 1.0 g/l to 40 g/l.
  • polyamide fibre material there comes into consideration natural polyamide fibre material, for example wool or silk, or synthetic polyamide fibre material, for example polyamide 6 or polyamide 6.6, or blends, for example wool/cellulose, polyamide/cellulose, polyamide/wool, polyamide/polyester or, especially, polyamide/elastane blends.
  • the fibre material is prefer ⁇ ably synthetic polyamide fibre material.
  • the textile material can be used in any form, for example in the form of fibre, yarn, woven fabric or knitted fabric.
  • the textile auxiliary according to the invention can be applied to the polyamide fibre material by customary dyeing or printing methods, for example by spray application or foam applica ⁇ tion, by the exhaust process or, preferably, the pad-dyeing process.
  • Special apparatus is not necessary. It is possible to use, for example, the customary dyeing apparatus, e.g. open baths, winch becks, jiggers or paddle, jet or circulatory apparatus.
  • the customary dyeing apparatus e.g. open baths, winch becks, jiggers or paddle, jet or circulatory apparatus.
  • the liquors may comprise further additives, for example wetting agents, anti-foams, levelling agents or agents that influence the properties of the textile material, for example softeners, flame-proofing agents or dirt-, water- and oil-repellants and also water-softeners and natural or synthetic thickeners, e.g. alginates and cellulose ethers.
  • wetting agents for example softeners, flame-proofing agents or dirt-, water- and oil-repellants and also water-softeners and natural or synthetic thickeners, e.g. alginates and cellulose ethers.
  • the method according to the invention can advantageously be used for the thermal stabilisation both of undyed polyamide (white goods), which may have been treated with a fluorescent whitening agent, and of dyed polyamide.
  • the method according to the invention is especially effective in the treatment of fluorescent whitened polyamide fibre material.
  • the textile auxiliary according to the invention can be applied before, during or after dyeing.
  • auxiliary When the auxiliary is used before dyeing, yellowing of the undyed goods during so-called pre-setting can be prevented or reduced. Furthermore, oxidative damage to the material during pre-setting, which can bring about a change in the dye uptake, is prevented.
  • the textile auxiliary according to the invention is preferably applied after dyeing of the polyamide fibre material with reactive or disperse dyes, with the exception of metal complex dyes.
  • the after-treatment of the dyed polyamide material with the textile auxiliary according to the invention brings about especially a certain degree of fibre protection during post-setting (heat setting) and effectively reduces the alteration in shade that frequently occurs in that process step, that is to say the shade remains constant, there is no dulling and no loss of colour strength.
  • the treatment of the polyamide fibre material with the textile auxiliary according to the invention also brings about an improvement in fastness to ozone, NO x and chlorine.
  • the invention accordingly relates also to a method of improving the fastness to ozone, NO x and chlorine of natural or synthetic polyamide fibre materials that are undyed, fluorescent whitened or dyed with reactive or disperse dyes, with the exception of metal complex dyes, wherein the fibre material is treated with a liquor comprising a compound of formula (1), as defined above.
  • So-called storage yellowing that is to say the yellowing that occurs during storage of the textile materials, can surprisingly also be effectively reduced by treatment with the textile auxiliary according to the invention. Resistance to storage yellowing is generally measured using the Courtaulds yellowing test.
  • the polyamide fibre materials treated with the textile auxiliary according to the invention have a high Courtaulds fastness.
  • the textile auxiliaries according to the invention may comprise as further additives, for example, wetting agents, dispersants or pH regulators.
  • Example 1 Treatment of fluorescent whitened polyamide
  • a PA 6.6 textured tricot is treated by the exhaust process with an aqueous liquor containing
  • Ultravon ® EL (dispersant, Ciba Specialty Chemicals). The pH is adjusted to 4.5 with acetic acid.
  • the whitened fabric is treated by the pad-dyeing process with an aqueous liquor containing different amounts of adipic acid dihydrazide.
  • the fabric is then subjected to a moulding test (30 s/210°C and 60 s/210°C); the whiteness values measured after the moulding test are given in Table 1 :
  • Example 2 Treatment of dyed polyamide A PA 6.6 textured tricot is dyed by the exhaust process with an aqueous liquor containing 0.02 % Tectilon ® Red 2B (Ciba Specialty Chemicals).
  • Table 2 gives the deviations in shade (DEF values) in comparison with the reference (untreated dyed fabric).
  • a PA 6.6 textured tricot is dyed by the exhaust process with an aqueous liquor containing
  • Table 3 shows the deviations in shade
  • Table 4 shows the whiteness values (Ganz) in comparison with the reference (untreated fabric).
  • a PA 6.6 textured tricot is treated with an aqueous liquor containing 20 g/l of adipic acid dihydrazide (ADH). Samples of the treated fabric are then washed three times, six times and ten times.
  • ADH adipic acid dihydrazide
  • Example 6 Moulding fastness of dyed polyamide A PA 6.6 textured tricot is, as described in Example 2, dyed with Tectilon ® Red 2B and then treated with adipic acid dihydrazide. After the moulding test, the deviations in shade (DEF values) in comparison with the reference (untreated dyed fabric) are measured (Table 6).
  • a PA 6.6 textured tricot is, as described in Example 4, dyed with Terasil ® Flavin 8GFF and then treated with adipic acid dihydrazide. After the moulding test, the deviations in shade (DEF values) in comparison with the reference (untreated dyed fabric) are measured (Table 7).
  • a PA 6.6 textured tricot (white goods) is, as described in Example 4, treated with adipic acid dihydrazide. After the moulding test, the whiteness (Ganz) in comparison with the reference (untreated fabric) is measured (Table 8).
  • a PA 6.6 textured tricot is fluorescent whitened with Uvitex ® NFW liquid and then treated with adipic acid dihydrazide, dried at 60 0 C and then subjected to heat- setting under different conditions.
  • Table 9 shows the measured whiteness values according to Ganz in comparison with the reference (fluorescent whitened fabric, without ADH treatment).
  • a PA 6.6 textured tricot is fluorescent whitened with Uvitex ® NFW liquid by the exhaust process.
  • DPEDA N.N'-diphenylethylenediamine

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

The invention relates to a method of improving the thermal stability of natural or synthetic polyamide fibre materials that are undyed, fluorescent whitened or dyed with reactive or disperse dyes, with the exception of metal complex dyes, wherein the fibre material is treated with a liquor comprising a compound of formula (1) Y1-X-Y2 (1) wherein X is a divalent aliphatic or cycloaliphatic radical and Y1 and Y2 are each independently of the other -OH, -CO-OR1, -NR1R2, -CO-NH-NR1R2 or -NH-CO-NH-NR1R2, wherein R1 and R2 are each independently of the other hydrogen; C1-C12alkyl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms; C5-C24- aryl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms; C6-C36aralkyl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms; or C5-C24cycloalkyl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms.

Description

Method of improving thermal stability
The present invention relates to a method of improving the thermal stability of undyed, fluorescent whitened or dyed, natural or synthetic polyamide fibre materials and to a textile auxiliary for use in that method.
In various textile-processing procedures (pretreatment, application of fluorescent whitening agents, dyeing, finishing), polyamide fibre materials are exposed to a heat treatment.
Particularly in the case of undyed goods and goods which may have been fluorescent whitened, this frequently results in undesirable yellowing.
The action of heat also often results in undesirable effects before and after dyeing.
For example, a thermal pretreatment may lead to oxidative damage to the polyamide, which manifests itself, for example, in increased yellowing or loss of tear strength or which may have an adverse effect on dyeability. During and after the dyeing process, a thermal treatment may result in unacceptable alterations in shade.
It has now been found that the above-mentioned disadvantageous effects can be substantially reduced by the use of a specific textile auxiliary.
The present invention relates to a method of improving the thermal stability of natural or synthetic polyamide fibre materials that are undyed, fluorescent whitened or dyed with reactive or disperse dyes, with the exception of metal complex dyes, wherein the fibre material is treated with a liquor comprising a compound of formula (1)
YrX-Y2 (1 )
wherein X is a divalent aliphatic or cycloaliphatic radical and
Yi and Y2 are each independently of the other -OH, -CO-ORi, -NRiR2, -CO-NH-NRiR2 or wherein Ri and R2 are each independently of the other hydrogen; Ci-Ci2alkyl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms; C5-C24- aryl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms; C6-C36aralkyl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms; or C5-C24CyClOaI kyl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms.
Aliphatic radicals X in formula (1) are, for example, ethylene, propylene, trimethylene, propane-1,1-diyl, tetramethylene, hexamethylene, octamethylene and decamethylene or linear or branched alkylene that is interrupted by one or more O atoms or -NH-, -N(alkyl)- or -N(alkylene-NH2)- groups.
Suitable cycloaliphatic radicals X are, for example, cyclohexane-1 ,2-diyl, cyclohexane-1 ,3- diyl and also CH / \_ CH and — / \ — / \__ .
CrCi2Alkyl as a radical Ri or R2 can be, for example, methyl, ethyl, n-propyl, isopropyl, n- butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, n-octyl or n-dodecyl.
A C5-C24aryl group as one of the radicals Ri - R5 is, for example, phenyl, tolyl, mesityl, isityl, naphthyl or anthryl.
Suitable C6-C36aralkyl groups are, for example, benzyl and 2-phenylethyl.
Examples of C5-C24cycloalkyl are cyclopentyl and cyclohexyl.
In the method according to the invention, preference is given to the use of compounds of formula (1) wherein X is ethylene, tetramethylene, hexamethylene or octamethylene.
Preference is also given to compounds of formula (1) wherein Y1 and Y2 are -NR1R2, -CO-NH-NR1R2 Or -NH-CO-NH-NR1R2, wherein R1 and R2 is hydrogen, CrC12alkyl or C5-C24aryl.
Special preference is given to compounds of formula (1 ) wherein Y1 and Y2 are -NR1R2, -CO-NH-NR1R2 or -NH-CO-NH-NR1R2, wherein R1 and R2 are hydrogen, methyl or phenyl.
Examples of suitable compounds of general formula (1) are the compounds of formulae (101) - (104)
The compounds of formula (1 ) are known and are commercially available or can be synthesised by known methods.
The compounds of formula (1) used in the method according to the invention are present in the liquor advantageously in an amount of from 0.1 g/l to 100 g/l, preferably from 0.5 g/l to 50 g/l and especially from 1.0 g/l to 40 g/l.
As polyamide fibre material there comes into consideration natural polyamide fibre material, for example wool or silk, or synthetic polyamide fibre material, for example polyamide 6 or polyamide 6.6, or blends, for example wool/cellulose, polyamide/cellulose, polyamide/wool, polyamide/polyester or, especially, polyamide/elastane blends. The fibre material is prefer¬ ably synthetic polyamide fibre material.
The textile material can be used in any form, for example in the form of fibre, yarn, woven fabric or knitted fabric. The textile auxiliary according to the invention can be applied to the polyamide fibre material by customary dyeing or printing methods, for example by spray application or foam applica¬ tion, by the exhaust process or, preferably, the pad-dyeing process.
Special apparatus is not necessary. It is possible to use, for example, the customary dyeing apparatus, e.g. open baths, winch becks, jiggers or paddle, jet or circulatory apparatus.
In addition to comprising water and the textile auxiliary, the liquors may comprise further additives, for example wetting agents, anti-foams, levelling agents or agents that influence the properties of the textile material, for example softeners, flame-proofing agents or dirt-, water- and oil-repellants and also water-softeners and natural or synthetic thickeners, e.g. alginates and cellulose ethers.
As mentioned above, the method according to the invention can advantageously be used for the thermal stabilisation both of undyed polyamide (white goods), which may have been treated with a fluorescent whitening agent, and of dyed polyamide.
In the case of undyed or fluorescent whitened polyamide, the yellowing caused by heat treatment during heat-setting (hot air) or during moulding processes (contact heat) is prevented or reduced.
The method according to the invention is especially effective in the treatment of fluorescent whitened polyamide fibre material.
In the thermal stabilisation of dyed polyamide, the textile auxiliary according to the invention can be applied before, during or after dyeing.
When the auxiliary is used before dyeing, yellowing of the undyed goods during so-called pre-setting can be prevented or reduced. Furthermore, oxidative damage to the material during pre-setting, which can bring about a change in the dye uptake, is prevented.
The textile auxiliary according to the invention is preferably applied after dyeing of the polyamide fibre material with reactive or disperse dyes, with the exception of metal complex dyes. The after-treatment of the dyed polyamide material with the textile auxiliary according to the invention brings about especially a certain degree of fibre protection during post-setting (heat setting) and effectively reduces the alteration in shade that frequently occurs in that process step, that is to say the shade remains constant, there is no dulling and no loss of colour strength.
In the case of undyed or fluorescent whitened polyamide materials, no appreciable reduction in whiteness is observed after the treatment with the textile auxiliary according to the invention.
It has also been found that, surprisingly, the treatment of the polyamide fibre material with the textile auxiliary according to the invention also brings about an improvement in fastness to ozone, NOx and chlorine.
The invention accordingly relates also to a method of improving the fastness to ozone, NOx and chlorine of natural or synthetic polyamide fibre materials that are undyed, fluorescent whitened or dyed with reactive or disperse dyes, with the exception of metal complex dyes, wherein the fibre material is treated with a liquor comprising a compound of formula (1), as defined above.
So-called storage yellowing, that is to say the yellowing that occurs during storage of the textile materials, can surprisingly also be effectively reduced by treatment with the textile auxiliary according to the invention. Resistance to storage yellowing is generally measured using the Courtaulds yellowing test. The polyamide fibre materials treated with the textile auxiliary according to the invention have a high Courtaulds fastness.
The textile auxiliaries according to the invention may comprise as further additives, for example, wetting agents, dispersants or pH regulators.
The following Examples serve to illustrate the invention. Unless otherwise indicated, temp¬ eratures are given in degrees Celsius, parts are parts by weight and percentages relate to percent by weight. Parts by weight relate to parts by volume in a ratio of kilograms to litres. Example 1 : Treatment of fluorescent whitened polyamide
(a) Whitening process
A PA 6.6 textured tricot is treated by the exhaust process with an aqueous liquor containing
2.0 % Uvitex® NFW liquid (fluorescent whitener, Ciba Specialty Chemicals) and 1.0 g/l of
Ultravon® EL (dispersant, Ciba Specialty Chemicals). The pH is adjusted to 4.5 with acetic acid.
Liquor ratio 1 :20, 30 min/95°C
(b) Application of auxiliary
The whitened fabric is treated by the pad-dyeing process with an aqueous liquor containing different amounts of adipic acid dihydrazide.
Liquor pick-up 100 %; drying at 700C
Whiteness according to Ganz: 230
The fabric is then subjected to a moulding test (30 s/210°C and 60 s/210°C); the whiteness values measured after the moulding test are given in Table 1 :
Table 1 :
Example 2: Treatment of dyed polyamide A PA 6.6 textured tricot is dyed by the exhaust process with an aqueous liquor containing 0.02 % Tectilon® Red 2B (Ciba Specialty Chemicals).
The fabric is then treated by the pad-dyeing process with an aqueous liquor containing 20 g/l of adipic acid dihydrazide (liquor pick-up 100 %; pH = 4-5), dried for 2 min at 120°C and then subjected to heat-setting under different conditions. Table 2 gives the deviations in shade (DEF values) in comparison with the reference (untreated dyed fabric).
Table 2:
Example 3: Treatment of dyed polyamide
A PA 6.6 textured tricot is dyed by the exhaust process with an aqueous liquor containing
0.65 % Terasil® Flavin 8GFF (Ciba Specialty Chemicals).
The fabric is then treated by the pad-dyeing process with an aqueous liquor containing 20 g/l of adipic acid dihydrazide (liquor pick-up 100 %; pH = 4-5), dried for 2 min at 120°C and then subjected to heat-setting under different conditions. Table 3 shows the deviations in shade
(DEF values) in comparison with the reference (untreated dyed fabric).
Table 3:
Example 4: Application to white goods
A PA 6.6 textured tricot is, as described in Example 3, treated by the pad-dyeing process with an aqueous liquor containing 20 g/l of adipic acid dihydrazide (liquor pick-up 100 %; pH = 4-5), dried for 2 min at 1200C and then subjected to heat-setting under different conditions. Table 4 shows the whiteness values (Ganz) in comparison with the reference (untreated fabric).
Table 4:
Example 5: Wash-fastness of the auxiliary
As described in Example 4, a PA 6.6 textured tricot is treated with an aqueous liquor containing 20 g/l of adipic acid dihydrazide (ADH). Samples of the treated fabric are then washed three times, six times and ten times.
After a moulding test, the whiteness according to Ganz is measured (Table 5).
Table 5:
Moulding Whiteness (Ganz) Whiteness (Ganz) reference (untreated) treated with ADH
Washing 400C 3x 6x 10x 3x 6x 10x
Set 30 s/210°C 27.6 19.2 23.0 39.9 41.4 40.1
Set 120 s/210°C -114.1 -127.5 -136 .9 8.5 10.1 -4.1
Set 240 s/210°C -140.0 -129.9 -136 .4 2.4 9.7 2.4
Example 6: Moulding fastness of dyed polyamide A PA 6.6 textured tricot is, as described in Example 2, dyed with Tectilon® Red 2B and then treated with adipic acid dihydrazide. After the moulding test, the deviations in shade (DEF values) in comparison with the reference (untreated dyed fabric) are measured (Table 6).
Example 7: Moulding fastness of dyed polyamide
A PA 6.6 textured tricot is, as described in Example 4, dyed with Terasil® Flavin 8GFF and then treated with adipic acid dihydrazide. After the moulding test, the deviations in shade (DEF values) in comparison with the reference (untreated dyed fabric) are measured (Table 7).
Example 8: Moulding fastness of treated white goods
A PA 6.6 textured tricot (white goods) is, as described in Example 4, treated with adipic acid dihydrazide. After the moulding test, the whiteness (Ganz) in comparison with the reference (untreated fabric) is measured (Table 8).
Example 9: Treatment of fluorescent whitened polyamide
As described in Example 1, a PA 6.6 textured tricot is fluorescent whitened with Uvitex® NFW liquid and then treated with adipic acid dihydrazide, dried at 600C and then subjected to heat- setting under different conditions. Table 9 shows the measured whiteness values according to Ganz in comparison with the reference (fluorescent whitened fabric, without ADH treatment).
Table < i:
Whiteness Whiteness (reference) (ADH treatment)
Untreated 243 6 204 9
Set 30 s/190 0C 230 3 219 3
Set 60 s/190 0C 150 7 210 6
Set 30 s/210 0C 174 6 216 5
Set 60 s/210 0C -38. 2 204 8
Example 10: Treatment of fluorescent whitened polyamide
As described in Example 1, a PA 6.6 textured tricot is fluorescent whitened with Uvitex® NFW liquid by the exhaust process. The fabric is then treated by the exhaust process with an aqueous liquor containing 2.0 % N.N'-diphenylethylenediamine (DPEDA) (pH = 5.0; liquor ratio 1 :20; 30 min/98°C) and then subjected to heat-setting under different conditions. Table 10 shows the measured whiteness values according to Ganz in comparison with the reference (fluorescent whitened fabric, without DPEDA treatment).

Claims

What is claimed is:
1. A method of improving the thermal stability of natural or synthetic polyamide fibre materials that are undyed, fluorescent whitened or dyed with reactive or disperse dyes, with the exception of metal complex dyes, wherein the fibre material is treated with a liquor comprising a compound of formula (1)
YrX-Y2 (1 )
wherein X is a divalent aliphatic or cycloaliphatic radical and
Yi and Y2 are each independently of the other -OH, -CO-ORi, -NRiR2, -CO-NH-NRiR2 or wherein Ri and R2 are each independently of the other hydrogen; CrCi2alkyl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms; C5-C24- aryl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms; C6-C36aralkyl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms; or C5-C24cycloalkyl unsubstituted or substituted by one or more hydroxy, amino or carboxyl groups or halogen atoms.
2. A method according to claim 1 , which comprises the use of a compound of formula (1 ) wherein X is ethylene, tetramethylene, hexamethylene or octamethylene.
3. A method according to claim 1 , which comprises the use of a compound of formula (1) wherein Yi and Y2 are -NRiR2, -CO-NH-NRiR2 or -NH-CO-NH-NRiR2, wherein Ri and R2 are hydrogen, Ci-Ci2alkyl or C5-C24aryl.
4. A method according to claim 1 , which comprises the use of a compound of formula (1) wherein Yi and Y2 are -NRiR2, -CO-NH-NRiR2 or -NH-CO-NH-NRiR2, wherein Ri and R2 are hydrogen, methyl or phenyl.
5. A method according to claim 1 , which comprises the use of a compound of formula (101) — (104)
O CH3
H H
H,CτNγN. Α H HΛcH 3,
CH3 O
(103),
6. A method according to any one of the preceding claims, wherein the compound of formula (1) is present in the liquor in an amount of from 0.1 g/l to 100 g/l.
7. A method according to any one of the preceding claims, wherein the treatment of the fibre material with the liquor comprising a compound of formula (1) is effected by the pad-dyeing process.
8. A method according to any one of the preceding claims, wherein fluorescent whitened polyamide fibre material is treated.
9. A method according to any one of the preceding claims, wherein polyamide fibre material that has been dyed with reactive or disperse dyes, with the exception of metal complex dyes, is treated, after dyeing, with a liquor comprising a compound of formula (1) according to claim 1.
10. A method of improving the fastness to ozone, NOx and chlorine of natural or synthetic polyamide fibre material that is undyed, fluorescent whitened or dyed with reactive or disperse dyes, with the exception of metal complex dyes, wherein the fibre material is treated with a liquor comprising a compound of formula (1) according to claim 1.
EP05811066A 2004-10-28 2005-10-19 Method of improving thermal stability Withdrawn EP1817452A1 (en)

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CN105133313B (en) * 2015-10-15 2017-09-19 东华大学 A kind of anti-yellowing agent for nylon
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JPH0827674A (en) * 1994-07-14 1996-01-30 Unitika Ltd Method for processing for preventing natural polyamide-based fiber from yellowing

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BRPI0517631A (en) 2008-10-14

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