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WO2006003125A1 - Procede de production de vetements a haute visibilite ou d'accessoires a haute visibilite - Google Patents

Procede de production de vetements a haute visibilite ou d'accessoires a haute visibilite Download PDF

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Publication number
WO2006003125A1
WO2006003125A1 PCT/EP2005/052978 EP2005052978W WO2006003125A1 WO 2006003125 A1 WO2006003125 A1 WO 2006003125A1 EP 2005052978 W EP2005052978 W EP 2005052978W WO 2006003125 A1 WO2006003125 A1 WO 2006003125A1
Authority
WO
WIPO (PCT)
Prior art keywords
dye
high visibility
formula
compound
total amount
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.)
Ceased
Application number
PCT/EP2005/052978
Other languages
English (en)
Inventor
Urs Lauk
Hanspeter Meyer
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
BASF Schweiz AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Huntsman Advanced Materials Switzerland GmbH
Ciba SC Holding AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ciba Spezialitaetenchemie Holding AG, Huntsman Advanced Materials Switzerland GmbH, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Publication of WO2006003125A1 publication Critical patent/WO2006003125A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • D06P3/34—Material containing ester groups
    • D06P3/36—Material containing ester groups using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/06—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
    • 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
    • D06P1/0004—General aspects of dyeing
    • D06P1/0012—Effecting dyeing to obtain luminescent or phosphorescent dyeings
    • 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
    • D06P1/16—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 dispersed, e.g. acetate, 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
    • 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
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
    • C08K5/353—Five-membered rings

Definitions

  • the present invention relates to a process for dyeing hydrophobic and hydrophilic fibre material in order to produce high visibility markers or high visibility clothing.
  • Fluorescent dyes can in principle be used in the production of warning clothing, such as warning vests, jackets and trousers, as well as warning markers, for example armbands, belts and hat covers.
  • warning clothing such as warning vests, jackets and trousers
  • warning markers for example armbands, belts and hat covers.
  • this requires a high luminous intensity and adequate in-use fastness properties; in addition, the dyes should exhibit a precisely defined orange-red colour.
  • Standard DIN EN 471 lays down the criteria for high visibility or warning clothing, which are to ensure their conspicuous appearance and hence their warning action.
  • the present invention relates to a process for dyeing textile fabrics of hydrophobic or hydrophilic fibre material intended for use as high visibility markers or high visibility clothing according to standard DIN EN 471, by introducing a fluorescent dye preparation into the fibres or applying such a preparation thereto, wherein the dye preparation comprises at least 80 % by weight, based on the total amount of dye, of a compound of formula (1)
  • Ri is hydrogen, methyl or chlorine.
  • the dye preparations according to the invention preferably comprise at least 90 % by weight, especially at least 95 % by weight and more especially at least 99 % by weight, based on the total amount of dye, of a compound of formula (1 ).
  • dye preparations that comprise the compound of formula (1) as the only dye, that is to say dye preparations comprising 100 % by weight, based on the total amount of dye, of a compound of formula (1).
  • the dye preparation according to the invention additionally comprises a UV absorber.
  • Preferred UV absorbers are 2-(2-hydroxyphenyl)-2H-benzotriazoles.
  • the amount of UV absorber is advantageously from 0.001 to 10.0 % by weight, preferably from 0.01 to 5.0 % by weight and especially from 0.1 to 1.0 % by weight, based on the amount of fibre material to be dyed.
  • the dye preparations according to the invention are advantageously prepared by grinding the dyes so that their particle size is on average from 0.1 to 10 microns.
  • the grinding can be carried out in the presence of dispersants.
  • the dried dye is ground with a dispersant or is kneaded into paste form with a dispersant and then dried in vacuo or by atomisation.
  • the preparations so obtained can be used, after the addition of water, to prepare printing pastes and dyebaths.
  • the dye preparations according to the invention can be used in the dyeing and printing of semi-synthetic and, especially, synthetic hydrophobic fibre materials, more especially textile materials. Textile materials composed of blends that contain such semi-synthetic or synthetic hydrophobic textile materials can likewise be dyed or printed using the dye preparations according to the invention.
  • Suitable semi-synthetic textile materials are especially cellulose 214 acetate and cellulose triacetate.
  • Synthetic hydrophobic textile materials consist especially of linear, aromatic polyesters, for example those of terephthalic acid and glycols, especially ethylene glycol, or condensation products of terephthalic acid and 1,4-bis(hydroxymethyl)cyclohexane; of polycarbonates, for example those from ⁇ , ⁇ -dimethyl-4,4-dihydroxy-diphenylmethane and phosgene, and of fibres based on polyvinyl chloride and on polyamide.
  • the process according to the invention is preferably used in the dyeing of polyesters and polyester blends.
  • polyester fibre materials are dyed in the exhaust process from aqueous dispersion in the presence of customary anionic or non-ionic dispersants and optionally customary swelling agents (carriers) at temperatures of from 80 to 140 0 C.
  • Cellulose 2 ⁇ A acetate is dyed preferably at approximately from 65 to 85 0 C and cellulose triacetate at temperatures up to 115 0 C.
  • the dye preparations according to the invention can also be used successfully in the dyeing of polyester blends, for example polyester/cellulose fibre, polyester/polyamide or polyester/- polyurethane blends.
  • the dye preparations according to the invention are suitable for dyeing in accordance with the thermosol process, in the exhaust and continuous process and for printing processes.
  • the exhaust process is preferred.
  • the liquor ratio is dependent on the nature of the appara ⁇ tus, the substrate and the form of make-up. It may, however, be selected within a wide range, for example from 1 :4 to 1 : 100, but is preferably from 1 :6 to 1:25. - A -
  • the said textile material can be in a variety of processing forms, for example in the form of a fibre, yarn or nonwoven, or in the form of a woven fabric or knitted fabric.
  • the customary thickeners will be used, for example modified or unmodified natural products, for example alginates, British gum, gum arabic, crystal gum, locust bean flour, tragacanth, carboxymethylcellulose, hydroxyethylcellulose, starch, or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
  • modified or unmodified natural products for example alginates, British gum, gum arabic, crystal gum, locust bean flour, tragacanth, carboxymethylcellulose, hydroxyethylcellulose, starch, or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
  • the dyeings produced by the process according to the invention fulfil the conditions of standard DIN EN 471, even after irradiation with xenon light.
  • the dye preparations according to the invention impart to the mentioned materials, especially to polyester material, dyeings having good in-use fastness properties and, especially, high thermal stability.
  • the invention relates also to the use of a dye preparation comprising at least 80 % by weight, based on the total amount of dye, of a compound of formula (1) according to claim 1 in the production of high visibility markers or high visibility clothing.
  • the compounds of formula (1 ) are also suitable for the production of mass-coloured plastics or polymeric colour particles.
  • the process for the production of coloured plastics or polymeric colour particles comprises mixing together a high molecular weight organic material and a tinctorially effective amount of a dye preparation according to the invention.
  • the colouring of high molecular weight organic substances with the dye preparation is carried out, for example, by mixing the dye preparation into those substrates using mixing or grinding apparatus and homogenising the mixture, with the result that the dye preparation becomes finely distributed in the high molecular weight material.
  • the high molecular weight organic material with the admixed dye preparation is then processed using processes known perse, for example calendering (especially in the colouring of PVC), compression moulding, extrusion, coating, spinning (wet and dry spinning processes, especially in the colouring of acetate, polyacrylonitrile and viscose, melt spinning processes), casting or injection moulding, whereby the coloured material acquires its final form.
  • calendering especially in the colouring of PVC
  • compression moulding especially in the colouring of PVC
  • extrusion coating
  • coating spinning
  • spinning wet and dry spinning processes, especially in the colouring of acetate, polyacrylonitrile and viscose, melt spinning processes
  • casting or injection moulding whereby the coloured material acquires its final form.
  • the admixing of the dye preparation can be carried out immediately prior to the actual processing step, for example by continuously feeding a pulverulent dye preparation and, at the same time, a granulated or pulverulent high molecular weight organic material, and optionally also additional ingredients, for example additives, directly into the intake zone of an extruder, where mixing takes place just before processing.
  • additional ingredients for example additives
  • the dye preparation it is preferable for the dye preparation to be mixed into the high molecular weight organic material beforehand, because more evenly coloured substrates can be obtained.
  • thermoplastic plastics especially in the form of fibres, granules or moulded articles, for example containers for solid or liquid substances, for example bottles.
  • Preferred high molecular weight organic materials suitable for colouring according to the invention are very generally polymers having a dielectric constant of > 2.5, especially polyester, polycarbonate (PC), polystyrene (PS), polymethyl methacrylate (PMMA), polyamide, polyethylene, polypropylene, styrene/acrylonitrile (SAN) or acrylo- nitrile/butadiene/styrene (ABS).
  • polyester polymethyl meth ⁇ acrylate and polycarbonate.
  • linear aromatic polyesters which can be obtained by polycondensation of terephthalic acid or naphthalene-2,6- dicarboxylic acid and glycols, especially ethylene glycol, or condensation products of terephthalic acid and 1,4-bis(hydroxymethyl)cyclohexane, for example polyethylene tereph- thalate (PET), polytrimethylene terephthalate (PTT), polyethylene naphthalene-2,6- dicarboxylate (PEN) or polybutylene terephthalate (PBTP); also polycarbonates, for example those from ⁇ , ⁇ -dimethyl-4,4-dihydroxy-diphenylmethane and phosgene.
  • PET polyethylene tereph- thalate
  • PTT polytrimethylene terephthalate
  • PEN polyethylene naphthalene-2,6- dicarboxylate
  • PBTP polybutylene terephthalate
  • polycarbonates for example those from ⁇ , ⁇ -
  • polyester granules (PET Arnite D04-300, DSM) are predried at 13O 0 C for
  • the homogeneous mixture is extruded in an extruder (twin screw 25 mm from CoIMn,
  • polyester granules (PET Arnite D04-300, DSM) are predried at 13O 0 C for
  • the homogeneous mixture is extruded in an extruder (twin screw 25 mm from Collin,
  • the resulting orange-red-coloured polyester granules exhibit good allround properties after processing, especially very good light fastness and high-temperature light fastness.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Coloring (AREA)

Abstract

L'invention concerne un procédé pour teindre des tissus textiles en matière fibreuse hydrophobe ou hydrophile, destinés à être utilisés comme vêtements à haute visibilité ou accessoires à haute visibilité selon la norme DIN EN 471. Ce procédé consiste à introduire une préparation de colorants fluorescents à l'intérieur des fibres ou à appliquer ladite préparation sur ces dernières, cette préparation de colorants contenant au moins 80 % en poids, sur la base de la quantité totale de colorants, d'un composé de formule (1), dans laquelle R1 désigne hydrogène, méthyle ou chlore.
PCT/EP2005/052978 2004-07-07 2005-06-27 Procede de production de vetements a haute visibilite ou d'accessoires a haute visibilite Ceased WO2006003125A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP04103202.0 2004-07-07
EP04103202 2004-07-07

Publications (1)

Publication Number Publication Date
WO2006003125A1 true WO2006003125A1 (fr) 2006-01-12

Family

ID=34929297

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2005/052978 Ceased WO2006003125A1 (fr) 2004-07-07 2005-06-27 Procede de production de vetements a haute visibilite ou d'accessoires a haute visibilite

Country Status (2)

Country Link
TW (1) TW200615336A (fr)
WO (1) WO2006003125A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2142411A1 (de) * 1970-08-26 1972-03-02 CIBA Geigy AG, Basel (Schweiz) Verfahren zur Herstellung von orangen Signalfarben der kationischen Reihe
DE2447878A1 (de) * 1973-10-17 1975-04-30 Sandoz Ag Cumarinverbindungen
DE2844299A1 (de) * 1977-10-13 1979-04-19 Ciba Geigy Ag Neue farbstoffe, deren herstellung und verwendung
EP0026463A1 (fr) * 1979-10-02 1981-04-08 Hoechst Aktiengesellschaft Procédé de teinture d'articles plans textiles en fibres de polyesters pour l'utilisation comme vêtements protecteurs de prévention
EP0046250A1 (fr) * 1980-08-20 1982-02-24 Bayer Ag Préparation tinctoriale et son utilisation comme couleur d'avertissement et de signalisation
EP0885936A2 (fr) * 1997-06-19 1998-12-23 Basf Aktiengesellschaft Mélanges de colorants

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2142411A1 (de) * 1970-08-26 1972-03-02 CIBA Geigy AG, Basel (Schweiz) Verfahren zur Herstellung von orangen Signalfarben der kationischen Reihe
DE2447878A1 (de) * 1973-10-17 1975-04-30 Sandoz Ag Cumarinverbindungen
DE2844299A1 (de) * 1977-10-13 1979-04-19 Ciba Geigy Ag Neue farbstoffe, deren herstellung und verwendung
EP0026463A1 (fr) * 1979-10-02 1981-04-08 Hoechst Aktiengesellschaft Procédé de teinture d'articles plans textiles en fibres de polyesters pour l'utilisation comme vêtements protecteurs de prévention
EP0046250A1 (fr) * 1980-08-20 1982-02-24 Bayer Ag Préparation tinctoriale et son utilisation comme couleur d'avertissement et de signalisation
EP0885936A2 (fr) * 1997-06-19 1998-12-23 Basf Aktiengesellschaft Mélanges de colorants

Also Published As

Publication number Publication date
TW200615336A (en) 2006-05-16

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