EP0584044B1 - Verfahren zur photochemischen und thermischen Stabilisierung von ungefärbten und gefärbten Polyesterfasermaterialien - Google Patents

Verfahren zur photochemischen und thermischen Stabilisierung von ungefärbten und gefärbten Polyesterfasermaterialien Download PDF

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Publication number
EP0584044B1
EP0584044B1 EP93810563A EP93810563A EP0584044B1 EP 0584044 B1 EP0584044 B1 EP 0584044B1 EP 93810563 A EP93810563 A EP 93810563A EP 93810563 A EP93810563 A EP 93810563A EP 0584044 B1 EP0584044 B1 EP 0584044B1
Authority
EP
European Patent Office
Prior art keywords
formula
acid
photochemical
undyed
compound
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.)
Expired - Lifetime
Application number
EP93810563A
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German (de)
English (en)
French (fr)
Other versions
EP0584044A1 (de
Inventor
Dieter Dr. Reinehr
Gerhard Dr. Reinert
Manfred Dr. Rembold
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.)
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
Ciba Spezialitaetenchemie Holding AG
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Filing date
Publication date
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Publication of EP0584044A1 publication Critical patent/EP0584044A1/de
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Publication of EP0584044B1 publication Critical patent/EP0584044B1/de
Anticipated expiration legal-status Critical
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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
    • 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
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65118—Compounds containing hydroxyl groups
    • 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
    • D06M13/152—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 having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • D06M13/165—Ethers
    • 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
    • D06M13/252—Mercaptans, thiophenols, sulfides or polysulfides, e.g. mercapto acetic acid; Sulfonium 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
    • 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
    • D06M13/358—Triazines
    • 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
    • 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
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65131—Compounds containing ether or acetal 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
    • D06P1/651—Compounds without nitrogen
    • D06P1/65168—Sulfur-containing compounds
    • D06P1/65187—Compounds containing sulfide or disulfide 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
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • 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 the photochemical and thermal stabilization of undyed and dyed polyester fiber materials.
  • Dyed or printed polyester fiber material can be damaged under the influence of light and especially when exposed to heat.
  • effective protection of these undyed and dyed fiber materials from UV radiation is essential.
  • the present invention therefore relates to a process for the photochemical and thermal stabilization of undyed and dyed polyester fiber materials with UV absorbers, which is characterized in that the fiber material is mixed with a compound of the formula treated in what R 2 C 1 -C 5 alkyl means.
  • C 1 -C 5 alkyl are straight-chain or branched alkyl radicals such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl.
  • the compounds of formula (1) are known, e.g. from CH-A-436,285. They can be prepared analogously to the process described in EP-A-0,395,938 by Friedel-Crafts alkylation of 1 mol of cyanuric chloride with one mol of an alkyl mercaptan and subsequent reaction with 2 mol of the corresponding benzene compound in the presence of a Lewis acid, preferably aluminum chloride.
  • EP-A-0 280 653 discloses a process for improving the photochemical stability of dyeings on polyester materials with UV absorbers which, in contrast to the UV absorber used according to the invention, contain an alkylthio group bonded to the triazine residue via an alkyl or phenyl bridge member .
  • US-A-3,293,249 discloses hydroxyphenyl-1,3,5-triazines, which differ explicitly from the hydroxyphenyl-1,3,5-triazines used according to the invention in that they have an alkyl radical bonded to the triazine via sulfur.
  • the UV absorbers according to the invention are used in an amount of 0.01 to 10% by weight, preferably 0.1 to 5% by weight, based on the weight of the fiber material.
  • the UV absorbers according to the invention are sparingly soluble in water and are therefore applied in dispersed form. To do this, they are treated with an appropriate dispersant using e.g. Quartz balls and a high-speed mixer are ground to a fineness of 1-2 ⁇ m.
  • Dispersions which are only slightly soluble in water are suitable as dyes. They are therefore largely in the form of a fine dispersion in the dyeing liquor. They 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 can also be used according to the invention.
  • Polyester fiber material that can be dyed or printed and treated with the UV absorbers mentioned is, for example, cellulose ester fibers, such as cellulose 21 ⁇ 2-acetate fibers and triacetate fibers and particularly linear polyester fibers, which may also be acid-modified, to be understood, for example, 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 polyester fiber material (PES) used almost exclusively in industry so far consists of terephthalic acid and ethylene glycol.
  • the fiber materials can also be used as a mixed fabric among themselves or with other fibers, e.g. Mixtures of polyacrylonitrile / polyester, polyamide / polyester, polyester / cotton, polyester / viscose and polyester / wool can be used and can be colored or printed discontinuously or continuously by known methods.
  • the textile material can be presented in various forms.
  • Piece goods such as knitted or woven fabrics, or yarn on cross-wound bobbins, warp beams, etc., are preferably used
  • Textile fabrics in the outer clothing sector which are translucent are also very suitable for the method according to the invention. If such textiles are treated by the process according to the invention, they can protect the skin tissue located under the transparent outer clothing fabric from the damaging influence of UV radiation.
  • the dyeings are carried out from an aqueous liquor using a continuous or batch process.
  • the liquor 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 dyeing liquors which in addition to the dyes may optionally contain other auxiliaries, are applied to the piece material by, for example, padding or slapping and developed by means of heat-setting or HT steaming processes.
  • Linear polyester fibers and cellulose fibers are preferably dyed by the so-called high-temperature process in closed and pressure-resistant apparatus at temperatures> 100 ° C., preferably between 110 ° and 135 ° C. and, if appropriate, under pressure.
  • Circulation apparatuses such as are suitable as closed vessels Cross-winder or tree dyeing machines, reel runners, nozzle or drum dyeing machines, muff dyeing machines, paddles or jiggers.
  • Cellulose-21 ⁇ 2-acetate fibers are preferably dyed at temperatures of 80-85 ° C.
  • the UV absorbers according to the invention are used in the dyeing application, they are used in such a way that the fiber material is first treated with these compounds and then the dyeing is carried out, or preferably the fiber material is simultaneously treated with the UV absorber and the dye in the dye bath.
  • the application of the UV absorber can also be retrofitted 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 dyeing liquors can also contain other additives such as dyeing aids, dispersants, carriers, wool protection and wetting agents and also defoamers.
  • the dye baths can also contain mineral acids, e.g. Contain 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. Contain 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 primarily serve to adjust the pH of the liquors used according to the invention, which is preferably between 4 and 5.
  • the fiber material is preferably allowed to run for 5 minutes at 40 to 80 ° C. in the bath, which contains the dye, the UV absorber and optionally further additives and is adjusted to a pH of 4.5 to 5.5 the temperature within 10 to 20 minutes to 125 to 130 ° C and treated for 15 to 90 minutes, preferably 30 minutes, at this temperature.
  • the dyeings are completed by cooling the dye liquor to 50 to 80 ° C., rinsing the dyeings with water and, if appropriate, cleaning in a conventional manner in an alkaline medium under reductive conditions. The dyeings are then rinsed again and dried. If vat dyes are used for the cellulose part, the goods are treated in the usual way first with hydrosulfite at a pH of 6 to 12.5 and then with an oxidizing agent and finally washed out.
  • the UV absorbers according to the invention are added to the printing pastes in the form of their aqueous dispersions.
  • the printing paste contains the corresponding UV absorber in amounts of 0.1 to 10%, preferably 0.1 to 5%, based on the weight of the printing paste.
  • the amount of dyes added to the printing pastes depends on the desired shade; In general, amounts of 0.01 to 15, preferably 0.02 to 10 percent by weight, based on the textile material used, have proven successful.
  • the printing pastes advantageously contain acid-stable thickeners, preferably of natural origin such as seed flour derivatives, in particular sodium alginate, alone or in a 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 hydrogenphosphate, preservatives, sequestering agents, emulsifiers, water-insoluble solvents, oxidizing agents or deaerating agents.
  • 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 polymethaphosphate, 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 fiber material is dried at temperatures up to 150 ° C., preferably 80 ° to 120 ° C.
  • the material is then fixed by heat treatment at temperatures of preferably 100 ° to 220 ° C.
  • the heat treatment is generally carried out with superheated steam under pressure.
  • the fixation can take place for 20 seconds to 10 minutes, preferably 4 to 8 minutes.
  • the prints are also finished in the usual way by rinsing with water and can, if appropriate, be carried out by additional cleaning in an alkaline medium under reductive conditions, e.g. be made with sodium dithionite. In the latter case, the printing stains are again rinsed, dewatered and dried.
  • the percentages relate to the weight.
  • the amounts relate to pure substance in the case of dyes and UV absorbers.
  • liquor (I) contains no further additives
  • liquors (II) and (III) are each additionally 0.6% of the compounds of the formulas respectively. admitted.
  • the jersey pieces are dyed in pressure bombs in the dispersed liquors. This is done at 50 ° C and after a treatment time of 5 minutes at 3 ° C / min Heated up to 130 ° C. At this temperature you dye for 45 minutes, cool to 50 ° C and rinse warm and cold with distilled water and dry.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Artificial Filaments (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
  • Decoration Of Textiles (AREA)
EP93810563A 1992-08-18 1993-08-09 Verfahren zur photochemischen und thermischen Stabilisierung von ungefärbten und gefärbten Polyesterfasermaterialien Expired - Lifetime EP0584044B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH256892 1992-08-18
CH2568/92 1992-08-18

Publications (2)

Publication Number Publication Date
EP0584044A1 EP0584044A1 (de) 1994-02-23
EP0584044B1 true EP0584044B1 (de) 1997-07-16

Family

ID=4236732

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93810563A Expired - Lifetime EP0584044B1 (de) 1992-08-18 1993-08-09 Verfahren zur photochemischen und thermischen Stabilisierung von ungefärbten und gefärbten Polyesterfasermaterialien

Country Status (8)

Country Link
US (1) US5649980A (ja)
EP (1) EP0584044B1 (ja)
JP (1) JP3243341B2 (ja)
KR (1) KR940004141A (ja)
AT (1) ATE155538T1 (ja)
BR (1) BR9303391A (ja)
DE (1) DE59306916D1 (ja)
ES (1) ES2106308T3 (ja)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0795640B1 (de) * 1996-03-13 2008-06-18 Huntsman Advanced Materials (Switzerland) GmbH Stabilisatorkombination
US20020019183A1 (en) * 1997-02-12 2002-02-14 Demott Roy P. Release barrier fabrics
EP0962586A1 (de) * 1998-06-05 1999-12-08 Ciba SC Holding AG Verfahren zur Verbesserung der photochemischen und thermischen Stabilität von Färbungen und Drucken auf Polyesterfasermaterialien
DE10002178A1 (de) 2000-01-20 2001-07-26 Mitsubishi Polyester Film Gmbh Matte, UV-stabile, koextrudierte Polyesterfolie, Verfahren zu ihrer Herstellung und ihre Verwendung
DE10002161A1 (de) 2000-01-20 2001-07-26 Mitsubishi Polyester Film Gmbh Matte, flammhemmend ausgerüstete koextrudierte Polyesterfolie, Verfahren zu ihrer Herstellung und ihre Verwendung
DE10002160A1 (de) * 2000-01-20 2001-07-26 Mitsubishi Polyester Film Gmbh Matte, UV-stabile, schwerentflammbare koextrudierte Polyesterfolie, Verfahren zu ihrer Herstellung und ihre Verwendung
DE10002151A1 (de) * 2000-01-20 2001-07-26 Mitsubishi Polyester Film Gmbh Amorphe, mehrschichtige, matte, thermoformbare Polyesterfolie, Verfahren zu ihrer Herstellung und ihre Verwendung
DE10002169A1 (de) 2000-01-20 2001-07-26 Mitsubishi Polyester Film Gmbh Matte, UV-stabile, thermoformbare, koextrudierte Polyesterfolie, Verfahren zu ihrer Herstellung und ihre Verwendung
US20050155163A1 (en) * 2004-01-21 2005-07-21 Griffin Bruce O. Dye mixtures
WO2010081625A2 (en) 2009-01-19 2010-07-22 Basf Se Organic black pigments and their preparation
US20240102236A1 (en) * 2018-10-03 2024-03-28 Huntsman Advanced Materials (Switzerland) Gmbh New Pyridine And Pyrimidine Substituted Triazine UV Absorbers

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3293249A (en) * 1964-05-04 1966-12-20 Ciba Ltd Hydroxyphenyl-triazines and process for their manufacture

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH436285A (de) * 1963-01-25 1967-05-31 Ciba Geigy Verwendung von neuen Aryl-1,3,5-triazinen als Schutzmittel gegen Ultraviolettstrahlung für nicht-textile organische Materialien
US4831068A (en) * 1987-02-27 1989-05-16 Ciba-Geigy Corporation Process for improving the photochemical stability of dyeings on polyester fibre materials
US4886518A (en) * 1987-10-01 1989-12-12 Ciba-Geigy Corporation Dyeing cellulose fibres without incurring ending with colorless pyrimidine, triazine, aromatic, furfuryl or quinolinyl compound
US4950304A (en) * 1987-10-02 1990-08-21 Ciba-Geigy Corporation Process for quenching or suppressing the fluorescence of substrates treated with fluorescent whitening agents
DE59010061D1 (de) * 1989-04-21 1996-02-29 Ciba Geigy Ag Verfahren zur Herstellung von 2-(2',4'-Dihydroxyphenyl)-4,6-diaryl-s-triazinen

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3293249A (en) * 1964-05-04 1966-12-20 Ciba Ltd Hydroxyphenyl-triazines and process for their manufacture

Also Published As

Publication number Publication date
JPH06200477A (ja) 1994-07-19
BR9303391A (pt) 1994-03-15
JP3243341B2 (ja) 2002-01-07
KR940004141A (ko) 1994-03-14
EP0584044A1 (de) 1994-02-23
ATE155538T1 (de) 1997-08-15
ES2106308T3 (es) 1997-11-01
US5649980A (en) 1997-07-22
DE59306916D1 (de) 1997-08-21

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