EP1891164A2 - Colorants de dispersion bleus resistant a la lumiere chaude - Google Patents

Colorants de dispersion bleus resistant a la lumiere chaude

Info

Publication number
EP1891164A2
EP1891164A2 EP06763372A EP06763372A EP1891164A2 EP 1891164 A2 EP1891164 A2 EP 1891164A2 EP 06763372 A EP06763372 A EP 06763372A EP 06763372 A EP06763372 A EP 06763372A EP 1891164 A2 EP1891164 A2 EP 1891164A2
Authority
EP
European Patent Office
Prior art keywords
dye
alkyl
phenyl
halogen
hydrogen
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Withdrawn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
EP06763372A
Other languages
German (de)
English (en)
Inventor
Hartwig Jordan
Andreas Endres
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.)
Dystar Colours Distribution GmbH
Original Assignee
Dystar Textilfarben GmbH and Co Deutschland KG
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 Dystar Textilfarben GmbH and Co Deutschland KG filed Critical Dystar Textilfarben GmbH and Co Deutschland KG
Publication of EP1891164A2 publication Critical patent/EP1891164A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/34—Anthraquinone acridones or thioxanthrones
    • C09B5/36—Amino acridones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/42—Pyridino anthraquinones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C09B67/0038—Mixtures of anthraquinones
    • 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 is in the field of disperse dyes.
  • dyes belonging to the class of anthraquinones are generally used.
  • the dyes of this type which are currently used in practice do not fully satisfy the high demands on lightfastness, in particular on the fastness to light of light. This is especially true for combinations with heat-yellow and red disperse dyes (so-called trichromatic), where it depends on the fact that the individual components of the trichromy fade to the same extent, so it does not cause sound changes under the action of light.
  • Anthrachinonacridone are also already described for dyeing polyester fibers.
  • the latter describes a process for dyeing and printing fibrous material from high molecular weight polyesters, in which, for example, anthraquinone-3,4-benzachedones are used which carry a butyrylamino or a ⁇ -chloropropionylamino radical in the 1-position.
  • these dyes already provide strong colorations with excellent fastness properties, but still have drawbacks on polyester on drawability.
  • the present invention thus relates to dyes of the general formula I.
  • R 1 to R 4 independently of one another represent hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, CF 3 , NO 2 , CN, halogen, COR 5 , COOR 5 , CONR 6 R 7 , SO 2 R 5 or SO 2 NR 6 R 7 , wherein R 5 , R 6 and R 7 are hydrogen or (Ci-C 4 ) alkyl, but R 6 and R 7 can not be simultaneously hydrogen; and Y is -CO (CH 2 ) 3 Cl or -SO 2 R 8 , wherein R 8 is (C 1 -C 8 ) alkyl, (C 1 -C 8 ) alkyl represented by NO 2 , CN, halogen or phenyl is substituted, phenyl, phenyl, by one or more
  • Substituents from the series (C r C 4 ) alkyl, (C r C 4 ) alkoxy, CF 3 , NO 2 , CN, halogen, COR 5 , COOR 5 , CONR 6 R 7 , SO 2 R 5 and SO 2 NR 6 R 7 is substituted, naphthyl or naphthyl (4 C r C) alkoxy substituted by one or more of the substituents from the series (C r C 4) -alkyl, CF 3, NO 2, CN, halogen, COR 5 , COOR 5 ,
  • R 8 can not stand for 4-methylphenyl, when R 1 to R 4 are hydrogen and can not stand for phenyl or 4-methylphenyl, when R 1 and R 3 are chlorine and R 2 and R 4 are hydrogen.
  • R 1 to R 7 (C r C 4 ) alkyl groups may be straight-chain or branched and are for example methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl or tert-butyl.
  • R 8 standing (Ci-C 8 ) alkyl groups may additionally still represent pentyl, hexyl, heptyl and octyl.
  • Particularly preferred alkyl groups are methyl and ethyl.
  • (C 1 -C 4 ) -alkoxy groups which are therefore particularly preferably methoxy or ethoxy.
  • Halogen is, for example, fluorine, chlorine and bromine, with chlorine and bromine being preferred.
  • the radicals R 1 to R 4 are preferably hydrogen.
  • Examples of the radical R 8 are in particular ethyl, n-propyl, i-propyl, n-butyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-chlorophenyl, 2-bromophenyl, A-bromophenyl, 2- Nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, phenylmethyl, 4-chloro-3-nitrophenyl, 3-trifluoromethylphenyl, 3,4-dimethoxyphenyl and 4-methoxyphenyl.
  • the dyes of the general formula I according to the invention can be used together with one or more dyes as are customarily used for dyeing polyester fibers or polyester textile matehals for automotive textiles.
  • the present invention thus also relates to dye mixtures which contain at least one dye of the general formula I and at least one dye which can be used for dyeing polyester textile materials for automotive fabrics.
  • Dyes that can be used to dye polyester textile materials for automotive fabrics are, in particular, azo, disazo, anthraquinone, nitro and naphthalimide dyes known to those skilled in the art.
  • Preferred yellow or orange dyes of this type are, for example, those listed in the Color Index Cl. Disperse Yellow 23, 42, 51, 59, 65, 71, 86, 108, 122, 163, 182 and 21 1, Cl.
  • R 9 to R 12 independently of one another represent hydrogen, chlorine, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, methoxy, ethoxy, n-propoxy, n-butoxy, methoxyethyl, ethoxyethyl, butoxyethyl or phenoxy and
  • R 13 is methyl, ethyl, propyl, isopropyl, allyl, n-butyl, isobutyl, n- and isopentyl, hexyl, octyl, 2-ethylhexyl, methoxyethyl, ethoxyethyl, butoxy ethyl,
  • Preferred red dyes of this type are, for example, those listed in the Color Index Cl. Dispers Red 60, 82, 86, 91, 92, 127, 134, 138, 159, 167, 191, 202, 258, 279, 284, 302 and 323, Cl. Solvent Red 176, as well as dyes of the formulas IV, V and VI
  • R 14 and R 15 independently of one another represent hydroxyethoxyethyl or phenyl
  • R 16 and R 17 independently of one another represent hydrogen, hydroxyethoxyethyl
  • R 18 for ((CC rr CC 88 )) - AAllkkyyll ,, PPhheennyyllooddeerr PPhhenyl which is substituted by (C r C 4 ) -alkyl, hydroxy or halogen, and
  • R 19 and I RR 2200 uunnaabbhphinnggii ⁇ g each other are hydrogen or halogen, and 0, 1 or 2 is.
  • Preferred blue or violet dyes of this type are, for example, those listed in the Color Index Cl. Blue 27, 54, 56, 60, 73, 77, 79, 79: 1, 87, 266, 333 and 361, Cl. Dispers Violet 27, 28, 57 and 95 and the dyes of formula VII
  • R 21 , R 22 and R 23 independently of one another are (C 1 -C 8 ) -alkyl, halogen or hydroxyl and m, o and p independently of one another are 0, 1 or 2.
  • dye (s) of the general formula I are in Amounts of 1 to 99 weight percent and dye (s) which may be used to dye polyester textile materials for automotive fabrics in amounts of 99 to 1 weight percent.
  • the dyes of the general formula I according to the invention can be obtained by methods known to the person skilled in the art.
  • Hal-Y (IX) wherein Hal is halogen, especially chlorine, and Y is as defined above.
  • This reaction can be carried out with or without the aid of acid-binding agents which are familiar to the person skilled in the art.
  • the compounds of the general formula VIII are obtainable, for example, by reacting bromamic acid of the formula X.
  • Anthranilic acid of general formula XI is preferably carried out in the presence of copper powder and a base under otherwise known to those skilled in the reaction conditions. The latter also applies to the other mentioned Reaktons Coloure.
  • the dyes and dye mixtures according to the invention are outstandingly suitable for dyeing and printing hydrophobic synthetic materials, wherein the dyeings and prints obtained have an exceptionally high light fastness and heat light fastness, so that the textiles dyed in this way can be used for the interiors of automobiles.
  • the dyestuffs according to the invention have, in particular, a better build-up capacity than the dyestuffs from WO 02/051942 and are furthermore superior to the dyestuffs described there in the fastness to light of light in light shades.
  • the present invention thus also relates to the use of dyes of the general formula I.
  • R 1 to R 4 independently of one another represent hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, CF 3 , NO 2 , CN 1, halogen, COR 5 , COOR 5 , CONR 6 R 7 , SO 2 R 5 or SO 2 NR 6 R 7 , wherein R 5 , R 6 and R 7 are hydrogen or (Ci-C 4 ) alkyl, but R 6 and R 7 can not be simultaneously hydrogen; and
  • Y is -CO (CH 2 ) 3 Cl or -SO 2 R 8 , where R 8 is (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkyl which is substituted by NO 2 , CN, halogen or phenyl is phenyl, phenyl (4 C r C) alkoxy substituted by one or more substituents from the series (C r C 4) -alkyl, CF 3, NO 2, CN, halogen, COR 5, COOR 5, CONR 6 R 7 , SO 2 R 5 and SO 2 NR 6 R 7 is substituted,
  • hydrophobic synthetic materials for example secondary cellulose-2 1/2 acetate, Cellulosethacetat, polyamides, and in particular high molecular weight polyesters.
  • Materials of high molecular weight polyesters are especially those based on polyethylene glycol terephthalates.
  • the hydrophobic synthetic materials may be in the form of flat or thread-like structures and be processed for example into yarns or woven, knitted or knitted fabrics.
  • Preferred are fibrous Textile materials. Very particular preference is given to polyester fibers and polyester textile materials for automotive upholstery materials.
  • dye mixtures containing at least one dye of the general formula I and at least one dye which can be used for dyeing polyester fibers and polyester textile materials for automotive fabrics are used.
  • Dyeing according to the invention can be carried out in a manner known per se, preferably from aqueous dispersion, if appropriate in the presence of carriers, between 80 to about 110 ° C. by the exhaustion process or after the HT process in the dye autoclave at 110 to 140 ° C, as well as after the so-called heat-setting process, wherein the goods are padded with the dyeing liquor and then fixed at about 180 to 230 ° C.
  • the printing of the materials mentioned can be carried out in a manner known per se so that the dyes or dye mixtures according to the invention are incorporated into a printing paste and the goods printed therewith for fixing the dye, optionally in the presence of a carrier, at temperatures between 180 to 230 ° C. is treated with HT steam, compressed steam or dry heat.
  • the dyestuffs and dyestuff mixtures according to the invention are particularly suitable for dyeing and printing polyester fibers and
  • Polyester textile materials for automotive fabrics It is preferred to carry out the dyeing and printing in the presence of UV absorbers, for example those based on benzophenone or benzotriazole. Details of dyeing and printing automotive trim fabrics are known to those skilled in the art and described in the pertinent literature.
  • hydrophobic synthetic materials such as alkalized Polyester fibers, polyester microfibers or non-fibrous materials.
  • the dyestuffs and dyestuff mixtures according to the invention should be in the finest possible distribution.
  • the fine distribution of the dyes is carried out in manner known per se, by slurrying the dye obtained in the fabrication together with dispersants in a liquid medium, preferably in water, and exposing the mixture to the action of shear forces, the originally present dye particles mechanically so far be crushed that an optimum specific surface area is achieved and the sedimentation of the dye is minimized. This is done in suitable mills, such as ball or sand mills.
  • the particle size of the dyes is generally between 0.5 and 5 Dm, preferably about 1 Dm.
  • the dispersants co-used in the milling process may be non-ionic or anionic.
  • Nonionic dispersants are, for example, reaction products of alkylene oxides, such as, for example, ethylene oxide or propylene oxide with alkylatable compounds, for example fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols and carboxamides.
  • Anionic dispersants are, for example, lignosulfonates, alkyl or alkylarylsulfonates or alkylaryl polyglycol ether sulfates.
  • the dye formulations thus obtained should be pourable for most applications.
  • the dye and dispersant content is therefore limited in these cases.
  • the dispersions are adjusted to a dye content of up to 50 percent by weight and a dispersant content of up to about 25 percent by weight. For economic reasons, dye shades of 15% by weight are usually not fallen below.
  • the dispersions may also contain other auxiliaries, for example those which act as oxidizing agents, for example sodium m-nitrobenzenesulfonate or fungicidal agents, for example sodium o-phenylphenolate and sodium pentachlorophenolate and in particular so-called "acid donors", such as Example butyrolactone, monochloroacetamide, Sodium chloroacetate, sodium dichloroacetate, the Na salt of 3-chloropropionic acid, half esters of sulfuric acid such as lauryl sulfate, and sulfuric acid esters of ethoxylated and oxypropylated alcohols such as butylglycol sulfate.
  • auxiliaries for example those which act as oxidizing agents, for example sodium m-nitrobenzenesulfonate or fungicidal agents, for example sodium o-phenylphenolate and sodium pentachlorophenolate and in particular so-called "acid donors", such as Example butyrolactone,
  • the dye dispersions thus obtained can be used very advantageously for the approach of dyeing liquors and printing pastes.
  • powder settings are preferred. These powders contain the dye or the dye mixture, dispersants and other auxiliaries, such as wetting, oxidation, preservation and
  • a preferred preparation process for pulverulent dye preparations consists in removing the liquid from the liquid dye dispersions described above, for example by vacuum drying, freeze-drying, drying on drum dryers, but preferably by spray-drying.
  • the required amounts of the dye formulations described above are diluted with the dyeing medium, preferably with water, to such an extent that a liquor ratio of 1: 5 to 1:50 results for the dyeing.
  • further dyeing auxiliaries such as dispersants, wetting agents and fixing aids, are generally added to the liquors.
  • organic and inorganic acids such as acetic acid, succinic acid, boric acid or phosphoric acid, a pH of 4 to 5, preferably 4.5, adjusted. It is advantageous to buffer the adjusted pH and to add a sufficient amount of a buffer system.
  • An advantageous buffer system is, for example, the acetic acid / sodium acetate system.
  • the required amounts of the above dye settings in a conventional manner together with thickeners, such as alkali alginates or the like, and optionally other additives, such as fixing accelerators, wetting agents and Oxidizing agents, kneaded to printing pastes.
  • thickeners such as alkali alginates or the like
  • additives such as fixing accelerators, wetting agents and Oxidizing agents
  • Formaldehyde 0.5 to 2 g per l of liquor monosodium phosphate and 2 g per l of a commercial commercial leveling agent added and adjusted with acetic acid to a pH of 4.5 to 5.5. 100 g of a textured polyester fabric based on polyethylene glycol terephthalate are introduced into the dyeing liquor obtained in this way and dyed at 130 ° C. for 60 minutes. After reductive NachrCenter gives a blue color of excellent light and hot light fastness and very good sublimation fastness.
  • Polyester velours to it. It is 45 min at 135 ° C with a heating rate of 1 grd / min dyed. After cooling, hot and cold rinsing. After reductive post-cleaning, a gray color of excellent heat-fastness is obtained. If this dyeing is carried out with the addition of 0.100 g of a UV absorber based on phenylthiazines or benzotriazoles, then gray dyeings of excellent fastness to light are also obtained. In the case of benzthazole, the fastness to lightfastness is somewhat higher than without the use of a UV absorber , Example 24

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

Colorants de formule générale (I) dans laquelle R<SUP>1</SUP> à R<SUP>4</SUP> et Y sont tels que définis dans la revendication 1, mélanges contenant ces colorants, procédés de production de ces colorants ainsi que leur utilisation pour teindre et imprimer des matières synthétiques hydrophobes.
EP06763372A 2005-06-02 2006-05-30 Colorants de dispersion bleus resistant a la lumiere chaude Withdrawn EP1891164A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200510025270 DE102005025270A1 (de) 2005-06-02 2005-06-02 Heißlichtechte blaue Dispersionsfarbstoffe
PCT/EP2006/062721 WO2006128869A2 (fr) 2005-06-02 2006-05-30 Colorants de dispersion bleus resistant a la lumiere chaude

Publications (1)

Publication Number Publication Date
EP1891164A2 true EP1891164A2 (fr) 2008-02-27

Family

ID=37401834

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06763372A Withdrawn EP1891164A2 (fr) 2005-06-02 2006-05-30 Colorants de dispersion bleus resistant a la lumiere chaude

Country Status (10)

Country Link
EP (1) EP1891164A2 (fr)
JP (1) JP2008542489A (fr)
KR (1) KR20080010430A (fr)
CN (1) CN101163754B (fr)
BR (1) BRPI0609651A2 (fr)
CA (1) CA2609780A1 (fr)
DE (1) DE102005025270A1 (fr)
MX (1) MX2007015154A (fr)
TW (1) TW200643113A (fr)
WO (1) WO2006128869A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101248789B1 (ko) * 2011-05-31 2013-04-03 한국니트산업연구원 Ｐｌａ 및 ｐｅｔ를 이용한 자동차 내장재 직물
TWI631174B (zh) * 2017-02-21 2018-08-01 蘇文淵 用於深色紡織物或工程塑膠的色母組成物及其製品

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1850482A (en) * 1926-05-31 1932-03-22 Gen Aniline Works Inc Production of new vat dyestuffs of the anthraquinone acridone series and the products
CH144867A (de) * 1929-08-01 1931-01-31 Ig Farbenindustrie Ag Verfahren zur Darstellung eines Küpenfarbstoffes.
DE579326C (de) * 1931-04-03 1933-06-23 I G Farbenindustrie Akt Ges Verfahren zur Herstellung von stickstoffhaltigen Kuepenfarbstoffen
US2185140A (en) * 1936-03-04 1939-12-26 Gen Aniline Works Inc Dyestuffs of the anthraquinone benzacridone series
DE665598C (de) * 1936-08-15 1938-09-30 I G Farbenindustrie Akt Ges Verfahren zur Herstellung von Kuepenfarbstoffen der Anthrachinonreihe
DE1171101B (de) * 1961-07-14 1964-05-27 Cassella Farbwerke Mainkur Ag Verfahren zur Herstellung von Farbstoffen der Anthrachinonreihe
NL249158A (fr) * 1960-08-05
DE19622356A1 (de) * 1996-06-04 1997-12-11 Bayer Ag Isoindoleninamidfarbstoffe
EP1085055B1 (fr) * 1999-09-20 2004-10-20 Ciba SC Holding AG Colorant azoique, procédé pour sa préparation et son utilisation pour la teinture ou l'impression de matériaux fibreux
AU2002217107A1 (en) * 2000-12-22 2002-07-08 Ciba Specialty Chemicals Holdings Inc. Dyeing or printing of manufactured natural polymer and synthetic hydrophobic fibre materials
EP1618154B1 (fr) * 2003-04-22 2008-09-17 Huntsman Advanced Materials (Switzerland) GmbH Composition de pigments / colorants

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006128869A3 *

Also Published As

Publication number Publication date
DE102005025270A1 (de) 2006-12-07
TW200643113A (en) 2006-12-16
CN101163754A (zh) 2008-04-16
WO2006128869A3 (fr) 2007-04-19
CA2609780A1 (fr) 2006-12-07
MX2007015154A (es) 2008-02-15
WO2006128869A2 (fr) 2006-12-07
BRPI0609651A2 (pt) 2010-04-20
KR20080010430A (ko) 2008-01-30
JP2008542489A (ja) 2008-11-27
CN101163754B (zh) 2011-05-11

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