EP0864687A2 - Procédé pour améliorer les solidités photochimiques des matériaux teints et imprimés à base de fibres de polyester - Google Patents

Procédé pour améliorer les solidités photochimiques des matériaux teints et imprimés à base de fibres de polyester Download PDF

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Publication number
EP0864687A2
EP0864687A2 EP98810183A EP98810183A EP0864687A2 EP 0864687 A2 EP0864687 A2 EP 0864687A2 EP 98810183 A EP98810183 A EP 98810183A EP 98810183 A EP98810183 A EP 98810183A EP 0864687 A2 EP0864687 A2 EP 0864687A2
Authority
EP
European Patent Office
Prior art keywords
formula
fiber material
polyester fiber
compound
treated
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Withdrawn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
EP98810183A
Other languages
German (de)
English (en)
Other versions
EP0864687A3 (fr
Inventor
Francesco Fuso
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.)
Novartis AG
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
Ciba Spezialitaetenchemie 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 Geigy AG, Ciba Spezialitaetenchemie Holding AG filed Critical Ciba Geigy AG
Publication of EP0864687A2 publication Critical patent/EP0864687A2/fr
Publication of EP0864687A3 publication Critical patent/EP0864687A3/fr
Withdrawn legal-status Critical Current

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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
    • D06M13/35—Heterocyclic compounds
    • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
    • 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
    • D06P1/6426—Heterocyclic compounds
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/25—Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments
    • 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
    • D06P3/40—Cellulose acetate
    • D06P3/42—Cellulose acetate 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
    • 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
    • D06P3/40—Cellulose acetate
    • D06P3/46—Cellulose triacetate
    • D06P3/48—Cellulose triacetate 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
    • 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
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • 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
    • Y10S8/922—Polyester fiber

Definitions

  • the present invention relates to a method for photochemical and thermal stabilization of dyeing and printing on polyester fiber materials and those containing polyester Mixed fibers.
  • Dyed or printed polyester fiber material can be under the influence of light and in particular be damaged while being exposed to heat.
  • R 1 , R 2 , R 3 and R 4 as C 1 -C 4 alkyl are methyl, ethyl, propyl, i-propyl, n-butyl, sec-butyl, i-butyl or tert. Butyl.
  • R 1 , R 2 and R 3 as C 1 -C 4 alkoxy are, for example, methoxy, ethoxy, propoxy, i-propoxy or butoxy.
  • Phenyl as a substituent in R 4 and the phenyl radicals in benzyloxy as a substituent in R 1 and R 2 can be further substituted one or more times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen.
  • Also preferred for the process according to the invention are compounds of the formula (1) in which R 3 is methyl, ethyl or n-butyl.
  • the compounds of formula (1) are e.g. known from US-A-3,896,125 or can according to known methods are produced.
  • the compounds used according to the invention are used in an amount of 0.01 to 5 % By weight, preferably 0.1 to 3% by weight, based on the weight of the fiber material, used.
  • the compounds used according to the invention are sparingly soluble in water and become therefore advantageously applied in dispersed form. To do this, they will use a appropriate dispersant using e.g. Quartz balls and a rapid mixer a fineness of 1-2 mm is ground.
  • Dispersions which are only slightly soluble in water are suitable as dyes. she are therefore mostly present in the dye liquor in the form of a fine dispersion. she can belong to different classes of dyes, for example the acridone, azo, Anthraquinone, coumarin, methine, perinone, naphthoquinone imine, quinophthalone, styryl, or nitro dyes. Mixtures of disperse dyes according to the invention can also be used be used.
  • polyester fiber material that is dyed or printed and with the compounds of the formula (1) can be treated are e.g. Cellulose ester fibers, e.g. Cellulose 24 acetate fiber and triacetate fibers and especially linear polyester fibers, which may also be acidic are modified to understand, e.g. by condensation of terephthalic acid with ethylene glycol or of isophthalic acid or terephthalic acid with 1,4-bis (hydroxymethyl) cyclohexane are obtained, as well as fibers from copolymers of terephthalic and isophthalic acid and ethylene glycol.
  • the linear that has been used almost exclusively in industry up to now Polyester fiber material (PES) consists of terephthalic acid and ethylene glycol.
  • the fiber materials can also be mixed with each other or with other fibers, e.g. Mixtures of polyacrylonitrile / polyester, polyamide / polyester, polyester / cotton, Polyester / viscose and polyester / wool, are used and by known methods discontinuously or continuously colored or printed.
  • the polyester fiber material can be presented in various forms. Preferably comes in piece goods, such as knitted fabrics, fiber composite or fabric, or also gam Cross-wound bobbins, warp beams, etc. into consideration.
  • Polyester textile fabrics and are also very suitable for the method according to the invention Textile blended fabrics containing polyester fibers in the outerwear sector that are translucent are. If such textiles are treated by the process according to the invention, you can see the skin tissue under the transparent outer clothing fabric protect against the damaging influence of UV radiation.
  • the dyeings are carried out from an aqueous liquor after a continuous or discontinuous one Method.
  • this can Fleet ratio can be selected in a wide range, e.g. 1: 4 to 1: 100, preferably 1: 6 to 1:50.
  • the temperature at which dyeing is carried out is at least 50 ° C and usually it is not higher than 140 ° C. It is preferably in the range from 80 to 135 ° C.
  • the dye liquors which in addition to the dyes, may be used may contain further aids, for example on the piece material Padding or padding applied and by means of heat setting or HT steaming processes developed.
  • Linear polyester fibers and cellulose fibers are preferably dyed according to the so-called High temperature processes in closed and pressure-resistant equipment Temperatures> 100 ° C, preferably between 110 ° and 135 ° C and optionally below Pressure.
  • Circulation apparatuses such as are suitable as closed vessels Cross-winder or tree dyeing machines, reel runners, jet or drum dyeing machines, Muff dyeing machines, paddles or jiggers.
  • Cellulose-24-acetate fibers are preferably dyed at temperatures of 80-85 ° C.
  • the UV absorbers according to the invention are used in the dyeing application, this is done the application so that the fiber material is first with these compounds treated and then carries out the coloring or preferably simultaneously Fiber material treated with the UV absorber and the dye in the dye bath.
  • the UV absorber can also be added to the finished coloring by means of heat setting, e.g. at 190 to 230 ° C in a period of 30 seconds to 5 Minutes.
  • the dye liquors can also contain other additives such as dyeing aids, dispersants, Carrier, wool protection and wetting agents as well as defoamers included.
  • the dye baths can also contain mineral acids, e.g. Sulfuric acid or phosphoric acid, or expediently organic acids, for example aliphatic carboxylic acids such as formic acid, acetic acid, oxalic acid or citric acid and / or salts such as ammonium acetate, ammonium sulfate or sodium acetate.
  • mineral acids e.g. Sulfuric acid or phosphoric acid
  • organic acids for example aliphatic carboxylic acids such as formic acid, acetic acid, oxalic acid or citric acid and / or salts such as ammonium acetate, ammonium sulfate or sodium acetate.
  • the acids serve especially the adjustment of the pH of the liquors used according to the invention, the is preferably between 4 and 5.
  • the fiber material is preferably left in the bath at 40 to 80 ° C. for 5 minutes contains the dye, the UV absorber and optionally other additives and on one pH is set to 4.5 to 5.5, the temperature increases within 10 to 20 minutes at 125 to 130 ° C and treated for 15 to 90 minutes, preferably 30 minutes, at this temperature further.
  • the dyeings are completed by cooling the dye liquor to 50 to 80 ° C. Rinse the dyeings with water and, if necessary, by cleaning in the usual way in an alkaline medium under reductive conditions. The stains then turn again rinsed and dried.
  • vat dyes for the cellulose content
  • the goods are first treated with hydrosulfite at a pH of 6 to 12.5 and then treated with an oxidizing agent and finally washed out.
  • UV absorbers used according to the invention are used for the production of prints expediently mixed with the printing pastes in the form of their aqueous dispersions.
  • the printing paste contains the corresponding UV absorber in quantities from 0.01 to 5% by weight, preferably 0.1 to 3% by weight, based on the weight of the printing paste.
  • the UV absorbers can already be used in the preparation of the pressure floor, e.g. after this Heat-setting processes can be applied.
  • the amount of dyes added to the printing pastes depends on the desired one Color shade; in general, amounts of 0.01 to 15, preferably 0.02 to 10 weight percent, based on the textile material used, proven.
  • the printing pastes contain expediently acid-stable thickeners, preferably more natural Origin such as corn flour derivatives, especially sodium alginate on its own or in Mixture with modified cellulose, in particular with preferably 20 to 25 percent by weight Carboxymethyl cellulose.
  • the printing pastes can also contain acid donors, such as butyrolactone or sodium hydrogen phosphate, preservatives, sequestering agents, Emulsifiers, water-insoluble solvents, oxidizing agents or deaerating agents contain.
  • Suitable preservatives are, above all, formaldehyde-releasing agents, such as, for example, paraformaldehyde or trioxane, especially aqueous, about 30 to 40 percent by weight formaldehyde solutions; as sequestering agents, for example sodium nitrilotriacetic acid, sodium ethylenediaminetetraacetic acid, especially sodium polymetaphosphate, in particular sodium hexamethaphosphate; as emulsifiers, especially adducts of an alkylene oxide and a fatty alcohol, in particular an adduct of oleyl alcohol and ethylene oxide; as water-insoluble solvents, high-boiling, saturated hydrocarbons, especially paraffins with a boiling range of about 160 to 210 ° C (so-called mineral spirits); as an oxidizing agent, for example an aromatic nitro compound, especially an aromatic mono- or dinitrocarboxylic acid or sulfonic acid, which is optionally present as an alkylene oxide ad
  • the printing paste becomes direct over the entire surface or in places applied to the fiber material, expediently printing machines more commonly Type, e.g. Gravure, rotary screen, flat film or inkjet machines be used.
  • the fiber material is preferably at temperatures up to 150 ° C. Dried 80 ° to 120 ° C.
  • the material is then fixed by heat treatment at temperatures from preferably 100 ° to 220 ° C.
  • the heat treatment is generally carried out with superheated steam under pressure.
  • the fixation can last 20 seconds to 12 minutes, preferably 4 to 8 Minutes.
  • the prints are also finished in the usual way by rinsing with water and can, if necessary, by additional cleaning in an alkaline medium under reductive Conditions, e.g. be made with sodium dithionite. In the latter case the prints are rinsed, dewatered and dried.
  • Draw the polyester fiber materials treated with the method according to the invention is also characterized by a very high sun protection factor.
  • the determination of the sun protection factor can e.g. after that of B.L. Diffey and J. Robson in J. Soc. Cosmet. Chem. 40, 127-133 (March / June 1989).
  • the dyeing liquor is adjusted to a pH of 5 with acetic acid, homogenized and added to the polyester tricot in the high-temperature dyeing apparatus and heated to 70 ° C. and then to 130 ° C. within 30 minutes.
  • the polyester jersey is dyed at this temperature for 60 minutes.
  • the liquor is then cooled to 75 ° C., the dyed polyester tricot is rinsed with hot and cold water and a reductive cleaning by treatment with a liquor containing 3 ml / l of a 30% aqueous solution of NaOH and 2 g / l sodium dithionite during Subjected for 20 minutes at 70 ° C.
  • the piece of polyester tricot is then rinsed with warm and cold water, centrifuged and dried at 80 ° C.
  • Example 1 The procedure is as described in Example 1 (a), but instead of 5 parts by weight of the compound of the formula (10), the same amount of the compound of the formula is used (f)
  • the procedure is as described in Example 1 (b), but instead of 0.5 g of the formulation comprising the compound of the formula (10), the same amount of a formulation of the compound of the formula (12) described under (e) is obtained also a gray-colored polyester jersey with good general fastness properties, especially very good hot light fastness.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
EP98810183A 1997-03-11 1998-03-04 Procédé pour améliorer les solidités photochimiques des matériaux teints et imprimés à base de fibres de polyester Withdrawn EP0864687A3 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH58397 1997-03-11
CH58397 1997-03-11
CH583/97 1997-03-11

Publications (2)

Publication Number Publication Date
EP0864687A2 true EP0864687A2 (fr) 1998-09-16
EP0864687A3 EP0864687A3 (fr) 1999-11-24

Family

ID=4190364

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98810183A Withdrawn EP0864687A3 (fr) 1997-03-11 1998-03-04 Procédé pour améliorer les solidités photochimiques des matériaux teints et imprimés à base de fibres de polyester

Country Status (2)

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US (1) US5984976A (fr)
EP (1) EP0864687A3 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5675647B2 (ja) 2009-01-19 2015-02-25 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 有機黒色顔料およびその製造
TWI835843B (zh) * 2018-10-03 2024-03-21 瑞士商亨斯邁紡織染化（瑞士）有限公司 新的經吡啶及經嘧啶取代之三ｕｖ吸收劑

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL302946A (fr) * 1963-01-24
ES2032594T3 (es) * 1987-02-27 1993-02-16 Ciba-Geigy Ag Procedimiento para mejorar la estabilidad fotoquimica de los colorantes sobre materiales de fibra de poliester. (reserva del art. 167.2 cpe).
US4831068A (en) * 1987-02-27 1989-05-16 Ciba-Geigy Corporation Process for improving the photochemical stability of dyeings on polyester fibre materials
EP0468921B2 (fr) * 1990-07-23 1998-07-22 Ciba SC Holding AG Dispersion aqueuse d'absorbant UV peu solubles
EP0523006B1 (fr) * 1991-07-12 1995-11-29 Ciba-Geigy Ag Procédé d'impression et de stabilisation photochimique de matériaux fibreux en polyester
US5298030A (en) * 1992-02-21 1994-03-29 Ciba-Geigy Corporation Process for the photochemical and thermal stabilization of undyed and dyed or printed polyester fiber materials

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Publication number Publication date
EP0864687A3 (fr) 1999-11-24
US5984976A (en) 1999-11-16

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