EP2699727B1 - Verfahren zum einfärben von polyester - Google Patents

Verfahren zum einfärben von polyester Download PDF

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Publication number
EP2699727B1
EP2699727B1 EP12707755.0A EP12707755A EP2699727B1 EP 2699727 B1 EP2699727 B1 EP 2699727B1 EP 12707755 A EP12707755 A EP 12707755A EP 2699727 B1 EP2699727 B1 EP 2699727B1
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Prior art keywords
textile material
hydrogen
alkyl
formula
treated
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English (en)
French (fr)
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EP2699727A1 (de
Inventor
Peter Scheibli
Gilles SPERISSEN
Marisa BIANCO
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Huntsman Advanced Materials Switzerland GmbH
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Huntsman Advanced Materials Switzerland GmbH
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters 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
    • 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
    • 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
    • D06P1/18—Azo 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
    • D06P1/44—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
    • 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
    • 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

Definitions

  • the present invention relates to a method of dyeing polyester-containing textile material.
  • Reduction sensitivity of azo disperse dyes is a problem in the polyester dyeing process.
  • the extent of dye destruction in the dye liquor depends on the chemical structure of the dye, the processing conditions and the type of dyeing auxiliaries. This reduction sensitivity seriously affects the reproducibility of the shade, especially in combination dyeings.
  • Critical dyeing conditions are fully flooded bulk dyeing machines, wherein the air and the oxygen are completely removed. Lignin sulfonate dispersing agents are widely used because of their low price and their reliability, especially at high dyeing temperatures (130 - 135°C), but due to their reduction power these dispersants tend to destroy reduction-sensitive disperse dyes in the dye liquor.
  • any disperse dye known for dyeing polyester can be used in the process according to the invention.
  • component (a) is a compound of formula or
  • the disperse dyes of formulae (2), (3) and (4) are known or can be prepared according to known methods.
  • disperse dyes are preferFred: C.I. Disperse Yellow 114, C.I. Disperse Yellow 211, C.I. Disperse Yellow 54, C.I. Disperse Orange 25, C.I. Disperse Orange 30, C.I. Disperse Orange 31, C.I. Disperse Orange 44, C.I. Disperse Orange 61, C.I. Disperse Red 50, C.I. Disperse Red 73, C.I. Disperse Red 82, C.I. Disperse Red 167, Disperse Red 167:1, C.I. Disperse Red 324, C.I. Disperse Red 356, C.I. Disperse Red 376, C.I. Disperse Red 382, C.I.
  • component (a) are the compounds of formula and
  • the compounds of formula (1) likewise are known and are described, for example, in WO 01/85857 .
  • the component (b) to be used in the method according to the invention also includes the ammonium salts obtainable by reaction of the compound of formula (1) with acids.
  • Suitable compounds of the formula (1a) are, for example, bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, 1-hydroxy-2,2,6,6-tetramethyl-4-acetoxypiperidinium citrate, 1-oxyl-2,2,6,6-tetramethyl-4-acetamidopiperidine, 1-hydroxy-2,2,6,6-tetramethyl-4-acetamidopiperidine, 1-hydroxy-2,2,6,6-tetramethyl-4-acetamidopiperidinium bisulfate, 1-oxyl-2,2,6,6-tetramethyl-4-oxopiperidine, 1-hydroxy-2,2,6,6-tetramethyl-4-oxopiperidine, 1-hydroxy-2,2,6,6-tetramethyl-4-oxopiperidinium acetate, 1-oxyl-2,2,6,6-tetramethyl-4-methoxypiperidine,
  • the textile material is treated with a liquor containing as component (b) 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine of the formula
  • the dyes according to component (a) can be applied individually or in mixtures.
  • mixtures of two or three dyes may be used.
  • Mixtures of four or more dyes can also be used, especially in the production of combination shades.
  • the amounts in which the individual dyes are used in the dye liquors can vary within wide limits depending on the desired depth of shade. In general, amounts of from 0.01 to 35 % by weight, especially from 0.1 to 15 % by weight, based on the fibre material to be dyed have proved to be advantageous.
  • the liquor ratio can be selected from within a wide range, for example within a range of from 1:2 to 1:50, preferably from 1:3 to 1:15.
  • the liquor can comprise, in addition to components (a) and (b) as defined above, further customary additives, such as dispersing, levelling and wetting agents, penetration accelerants, pH-regulators and antifoams.
  • further customary additives such as dispersing, levelling and wetting agents, penetration accelerants, pH-regulators and antifoams.
  • Suitable dispersing agents can be nonionic or anionic.
  • Nonionic dispersing agents are, for example, reaction products of alkylene oxides, like ethylene oxide or propylene oxide, with fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols and carboxamides.
  • Anionic dispersing agents are, for example, lignin sulfonates and salts thereof, alkyl- or alkylaryl-sulfonates, alkylaryl polyglycol ether sulfates, alkali metal salts of the condensation products of naphthalenesulfonic acids and formaldehyde, polyvinyl sulfonates and ethoxylated novolaks.
  • the textile material is treated with a liquor additionally containing a lignin sulfonate as dispersing agent.
  • the textile material can be used in any form, e.g. in the form of fibres, yarn, woven fabric, knitted fabric or non-woven.
  • Polyester-containing textile material in terms of the invention includes pure polyester as well as blends containing polyester and further synthetic, semi-synthetic or natural textile material, like polyester/cotton, polyester/wool or polyester/elastan blends.
  • the textile material is polyester or a polyester/cotton blend.
  • polyester fibre materials are dyed from an aqueous dispersion by the exhaust process in the presence of customary anionic or nonionic dispersants and in the presence or absence of customary swelling agents (carriers) at pH 3.5 - 5.5, in particular at pH 4.0 - 5.0, in the temperature range from 80 to 150 °C, preferably from 90 to 140 °C.
  • Special apparatus is not required.
  • customary dyeing apparatus e.g. open baths, winch becks, jigs, or paddle, jet or circulation apparatus, may be used.
  • an aftertreatment can be carried out at a pH value of e.g. from 7 to 12, especially from 7 to 9, and a temperature of e.g. from 30 to 100 °C, especially from 50 to 80 °C, to remove any unfixed dye.
  • unfixed dye can advantageously be removed reductively, by adding to the alkaline aftertreatment bath a reducing agent, for example a hydrosulfite, e.g. sodium hydrosulfite.
  • Dye that has been fixed in the fibre material is not attacked by the treatment.
  • the amount of reducing agent added is e.g. from 0.1 to 8.0 % by weight, especially from 0.5 to 5.0 % by weight, based on the weight of the aftertreatment bath.
  • 10 g knitted 100% polyester fabric is dyed in an autoclave by preparing a dye liquor of 100 ml total volume containing 45 mg of a commercial formulation of C.I. Disperse Blue 165:1, 50 mg of a compound of formula (101), 200 mg of a commercial dispersing agent (REAX 85A, lignin sulfonate, supplied by BASF), 50 mg of a commercial wetting and defoaming agent (ALBAFLOW ® UNI, supplied by Huntsman), 100 mg ammonium sulfate and about 0.1 ml of acetic acid 80% to get pH of 4.5.
  • a commercial dispersing agent RX 85A, lignin sulfonate, supplied by BASF
  • ABAFLOW ® UNI commercial wetting and defoaming agent
  • the fabric is put into the dye liquor and just before closing the autoclave it is thoroughly washed with nitrogen to simulate a fully flooded bulk dyeing machine, where all the air and the oxygen with it is removed completely.
  • the liquor is heated up with 2 °C per minute to 135 °C and is kept at 135 °C for 60 minutes.
  • After a warm and cold rinse the dyeing is treated in a reductive clearing: 20 min/70 °C in a liquor containing 5 ml/l caustic soda 36°Be, 2 g/l sodium hydrosulfite conc. and 1 g/l of a commercial nonionic washing agent (ERIOPON ® OL, supplied by Huntsman).
  • the dyeing is rinsed, neutralized and dried.
  • the depth of shade is determined by reflectance measurement and expressed in percentage in relation to the depth of shade which is obtained by a benchmark process carried out with same fabric, dye and auxiliaries but using UNIVADINE ® DP (dispersing agent, supplied by Huntsman) instead of the compound of formula (101), which is set as 100%.
  • Example 1 and Comparative Example 2 are repeated with other dyes. The resulting depth of shade values are summarized in Table 1.
  • Table 1 Series with 100% polyester fabric Comparative Example 2
  • Example 1 45 mg C.I. Disperse Blue 165:1 30% 71% 51 mg C.I. Disperse Blue 79.1 73% 98% 70 mg C.I. Disperse Blue 378 76% 93%
  • Inventive Example 1 and Comparative Example 2 is made with a fabric blend of 65% grey cotton and 35% polyester instead of the 100% polyester fabric and without the 200 mg of commercial lignin sulfonate dispersing agent (REAX 85A) in the comparative example 1 and in the inventive example 2.
  • REAX 85A commercial lignin sulfonate dispersing agent
  • Table 2 Series with fabric blend of 65% cotton / 35% polyester without REAX 85A Comparative Example 2 Inventive Example 1 45 mg C.I. Disperse Blue 165:1 45% 62% 51 mg C.I. Disperse Blue 79:1 68% 87% 70 mg C.I. Disperse Blue 378 73% 85%
  • Comparative Example 2 and Example 1 is made with a fabric blend of 65% cotton and 35% polyester instead of the 100% polyester fabric and without the 200 mg of commercial lignin sulfonate dispersing agent (REAX 85A) and without the washing with nitrogen.
  • the resulting depth of shade values are summarized in Table 3.
  • Table 3 Series with fabric blend of 65% cotton / 35% polyester without REAX 85A and without nitrogen washing Comparative Example 2
  • Inventive Example 1 45 mg Disperse Blue 165:1 81% 92% 51 mg Disperse Blue 79:1 85% 92% 70 mg Disperse Blue 378 90% 92%
  • 5 g knitted 100% polyester fabric is dyed in an autoclave with a dye liquor of 50 ml total volume containing 75 mg of a commercial formulation of C.I. Disperse Red 277 (Solvent Red 197), 20 mg of a compound of formula (101), 100 mg of a commercial wetting and defoaming agent (ALBAFLOW ® UNI, supplied by Huntsman), 50 mg ammonium sulfate and about 0.05 ml of acetic acid 80% to get pH of 4.5.
  • the liquor is heated up with 2 °C per minute to 135 °C and is kept at 135 °C for 60 minutes.
  • the dyeing After a warm and cold rinse the dyeing is subjected to a reductive aftertreatment: 20 min/70 °C in a liquor containing 5 ml/l caustic soda 36°Bé, 2 g/l sodium hydrosulfite conc. and 1 g/l of a commercial nonionic washing agent (ERIOPON ® OL, supplied by Huntsman). The dyeing is rinsed, neutralized and dried.
  • ERIOPON ® OL commercial nonionic washing agent
  • the dyeing of the Inventive Example 3 provides a significantly more brilliant shade and a significantly stronger fluorescence compared to the dyeing of the Comparative Example 4.
  • Example 3 and 4 are repeated by replacing 75 mg Disperse Red 277 with 75 mg Disperse Red 362 (Solvent Red 196) providing the same positive effect on shade and fluorescence in the case of Example 5 (use of the compound of formula (101)) compared to Example 6.

Landscapes

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

Claims (9)

  1. Verfahren zur Färbung von Polyester enthaltendem Textilmaterial, dadurch gekennzeichnet, dass das Textilmaterial mit einer Lauge behandelt wird, die enthält:
    (a) mindestens einen Dispersionsfarbstoff und
    (b) mindestens eine Verbindung der Formel
    Figure imgb0021
     worin
    G1 und G2 unabhängig voneinander C1-C4-Alkyl sind oder zusammen Pentamethylen bilden,
    Z1 und Z2 Methyl sind oder Z1 und Z2 zusammen ein Brückenglied bilden, welches unsubstituiert oder durch einen Ester-, Ether-, Hydroxyl-, Oxo-, Cyanhydrin-, Amido-, Amino-, Carboxyl- oder Urethanrest substituiert ist und
    E Oxyl oder Hydroxyl darstellt.
  2. Verfahren nach Anspruch 1, worin das Textilmaterial mit einer Lauge behandelt wird, die als Komponente (a) eine Verbindung der Formel
    Figure imgb0022
    Figure imgb0023
     oder
    Figure imgb0024
     enthält, worin R1 C1-C4-Alkyl bedeutet
    R2 Wasserstoff, Brom, Chlor, Cyano oder Nitro ist,
    R3 Brom, Chlor, Cyano oder Nitro ist,
    R4 Wasserstoff, Methyl oder Methoxy darstellt,
    R5 und R6 unabhängig voneinander Ethyl, Benzyl, 2-Cyanoethyl, 2-Hydroxyethyl, 2-Methoxyethyl, 2-Ethoxyethyl, 2-(2-Methoxyethoxy)-ethyl, 2-(2-Ethoxyethoxy)-ethyl, 2-Acetyloxyethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, 1-Methoxycarbonylethyl oder 1-Ethoxycarbonylethyl sind,
    R7 Wasserstoff, Brom, Chlor, Cyano oder Nitro ist,
    R8 Brom, Chlor, Cyano oder Nitro ist,
    R9 Methyl oder Ethyl darstellt und
    R10 Wasserstoff, Methyl, Methoxy, Acetylamino oder Propionylamino ist.
  3. Verfahren nach Anspruch 1, worin das Textilmaterial mit einer Lauge behandelt wird, die als Komponente (a) eine Verbindung der Formel enthält:
    Figure imgb0025
    Figure imgb0026
    Figure imgb0027
     oder
    Figure imgb0028
  4. Verfahren nach einem der vorangehenden Ansprüche, worin das Textilmaterial mit einer Lauge behandelt wird, die als Komponente (b) eine Verbindung der Formel enthält
    Figure imgb0029
    worin E Oxyl oder Hydroxyl ist,
    R11 Wasserstoff oder Methyl ist und
    n = 1 oder 2 ist,
    wenn n = 1 ist,
    stellt Y Wasserstoff, C1-C18-Alkyl, C2-C10-Alkenyl, Propargyl, Glycidyl oder C2-C50-Alkyl dar, welches unsubstituiert oder durch 1-10 Hydroxylgruppen substituiert ist und welches durch 1-20 Sauerstoffatome unterbrochen sein kann, oder
    stellt Y C1-C4-Alkyl, substituiert durch COOR12, dar, worin R12 Wasserstoff, C1-C4-Alkyl oder Phenyl ist,
    wenn n = 2 ist,
    stellt Y C1-C12-Alkylen, C4-C12-Alkenylen, Xylylen oder C1-C50-Alkylen dar, welcher unsubstituiert oder durch 1-10 Hydroxylgruppen substituiert ist und welches durch 1-20 Sauerstoffatome unterbrochen sein kann.
  5. Verfahren nach einem der vorangehenden Ansprüche, worin das Textilmaterial mit einer Lauge behandelt wird, die als Komponente (b) 1-Oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidin der Formel
    Figure imgb0030
     enthält.
  6. Verfahren nach einem der vorangehenden Ansprüche, worin das Textilmaterial mit einer Lauge behandelt wird, die zusätzlich ein Ligninsulfonat enthält.
  7. Verfahren nach einem der vorangehenden Ansprüche, worin das Textilmaterial Polyester oder eine Polyester/Baumwollmischung darstellt.
  8. Verfahren nach einem der vorangehenden Ansprüche, worin der Behandlung mit der Färbelauge eine reduktive Nachbehandlung folgt.
  9. Verfahren nach Anspruch 8, worin Natriumhydrosulfit in dem reduktiven Nachbehandlungsschritt verwendet wird.
EP12707755.0A 2011-04-20 2012-03-07 Verfahren zum einfärben von polyester Active EP2699727B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP12707755.0A EP2699727B1 (de) 2011-04-20 2012-03-07 Verfahren zum einfärben von polyester

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP11163130 2011-04-20
EP12707755.0A EP2699727B1 (de) 2011-04-20 2012-03-07 Verfahren zum einfärben von polyester
PCT/EP2012/053882 WO2012143167A1 (en) 2011-04-20 2012-03-07 Method of dyeing polyester

Publications (2)

Publication Number Publication Date
EP2699727A1 EP2699727A1 (de) 2014-02-26
EP2699727B1 true EP2699727B1 (de) 2014-11-19

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Country Status (9)

Country Link
US (1) US20140041134A1 (de)
EP (1) EP2699727B1 (de)
JP (1) JP5913566B2 (de)
KR (1) KR101902752B1 (de)
CN (1) CN103502528B (de)
BR (1) BR112013026857B8 (de)
ES (1) ES2528911T3 (de)
TW (1) TWI540236B (de)
WO (1) WO2012143167A1 (de)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2943652T3 (es) * 2017-06-28 2023-06-15 Huntsman Textile Effects Switzerland Gmbh Colorantes azo dispersados
CN114437564B (zh) * 2022-02-28 2024-04-02 浙江万丰化工股份有限公司 一种高牢度分散染料组合物及其应用
CN116082857A (zh) * 2022-12-27 2023-05-09 浙江闰土股份有限公司 蓝色分散染料组合物、蓝色分散染料及其制备方法和用途
CN115850997B (zh) * 2022-12-27 2024-04-12 浙江闰土股份有限公司 蓝色分散染料组合物、蓝色分散染料及其制备方法和用途

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE788960A (fr) * 1971-09-18 1973-03-19 Hoechst Ag Procede de realisation de teintures et impressions solides a lalumiere sur des fibres synthetiques
JPS5423783A (en) * 1977-07-15 1979-02-22 Sanyo Chemical Ind Ltd High temperature dyeing of polyester fiber
JPS5936035B2 (ja) * 1980-05-13 1984-08-31 住友化学工業株式会社 疎水性繊維材料の染色方法
JPS60252785A (ja) * 1984-05-29 1985-12-13 共同薬品株式会社 光堅牢度の優れたポリエステル系染色糸又は染色織布
EP0409771A3 (en) * 1989-06-27 1991-06-12 Ciba-Geigy Ag Process of photochemical and thermal stabilization of polyamide fibres, dyeable by acid and basic dyes, and of their mixtures amongst themselves and with other fibres
KR100849438B1 (ko) 2000-05-11 2008-07-31 시바 홀딩 인크 수성 목재 착료를 사용하는 목재의 착색방법
ATE329973T1 (de) * 2001-01-16 2006-07-15 Ciba Sc Holding Ag Tintenstrahldrucktinte und -aufzeichnungsmaterial
ES2342594T3 (es) * 2002-05-02 2010-07-09 Basf Se Productos estabilizados para el cuidado personal y productos para el hogar.
EP1680541B1 (de) * 2003-11-03 2012-12-19 Basf Se Stabilisierte körperpflegemittel, haushaltsprodukte, textilien und textile flächengebilde
JP2009526921A (ja) * 2006-02-17 2009-07-23 ハンツマン アドバンスト マテリアルズ （スイッツァランド） ゲーエムベーハー ポリエステルを染色するための方法

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Publication number Publication date
ES2528911T3 (es) 2015-02-13
KR20140025476A (ko) 2014-03-04
KR101902752B1 (ko) 2018-10-02
EP2699727A1 (de) 2014-02-26
US20140041134A1 (en) 2014-02-13
CN103502528A (zh) 2014-01-08
BR112013026857B8 (pt) 2023-05-16
TW201303112A (zh) 2013-01-16
TWI540236B (zh) 2016-07-01
WO2012143167A1 (en) 2012-10-26
BR112013026857B1 (pt) 2020-09-29
CN103502528B (zh) 2017-10-20
JP2014516390A (ja) 2014-07-10
JP5913566B2 (ja) 2016-04-27

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