EP0793692A1 - Melanges de colorants azo pour teintes noires - Google Patents

Melanges de colorants azo pour teintes noires

Info

Publication number
EP0793692A1
EP0793692A1 EP95937884A EP95937884A EP0793692A1 EP 0793692 A1 EP0793692 A1 EP 0793692A1 EP 95937884 A EP95937884 A EP 95937884A EP 95937884 A EP95937884 A EP 95937884A EP 0793692 A1 EP0793692 A1 EP 0793692A1
Authority
EP
European Patent Office
Prior art keywords
dye
hydrogen
weight
formula
chlorine
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Withdrawn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
EP95937884A
Other languages
German (de)
English (en)
Inventor
Uwe Nahr
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 SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP0793692A1 publication Critical patent/EP0793692A1/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Withdrawn legal-status Critical Current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
    • 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
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes

Definitions

  • the present invention relates to new dye mixtures containing, based in each case on the total weight of the dyes,
  • R 1 nitro or -CC -Al ylsulfonyl, which is optionally substituted by hydroxy
  • R 2 and R 3 are each independently hydrogen or chlorine or R 2 bromine and R 3 hydrogen or bromine
  • R 4 and R 5 are each independently hydrogen or chlorine
  • R 6 and R 7 each independently of one another are hydrogen, phenyl or C 1 -C 4 -alkyl, which is optionally substituted by hydroxy, phenoxy, 2-cyanoethoxy, acetyloxy, phenoxyacetyloxy, benzoyloxy, methoxycarbonyloxy or phenylaminocarbonyloxy, or when R 2 and R 3 each represent hydrogen or chlorine, including C 1 -C 4 cyanoal yl,
  • X 1 is hydrogen, hydroxy, methoxy, acetylamino or nitro
  • X 2 , X 3 , X 4 and X 5 are each independently hydrogen, methyl or methoxy and
  • X 6 is hydroxy, 2-hydroxyethoxy, formyl or methoxycarbonylamino, and d) 0 to 5% by weight of at least one azo dye of the formula V.
  • Z 2 is hydrogen or methoxy
  • Dye preparations containing the new dye mixtures, the use of the new dye mixtures for dyeing polyester in textile form and a process for dyeing polyester in textile form are included in Dye preparations containing the new dye mixtures, the use of the new dye mixtures for dyeing polyester in textile form and a process for dyeing polyester in textile form.
  • dye mixtures are known from EP-A 590438 which contain the dyes of the formulas I, Ha, III, IV and, if appropriate, IIb.
  • textiles dyed with these dye mixtures show a different shade under different types of light, this effect being further enhanced by the aftertreatment with an finishing agent (silicone oil based on an amino-functional polysiloxane).
  • the object of the present invention was to provide new dye mixtures which also contain the dyes of the formula I, Ha, III, IV and, if appropriate, Ilb.
  • the new hybrids should produce black shades and should have good application properties, in particular an unchanged neutral evening color.
  • 'Neutral evening color' means that a color in daylight and incandescent light looks the same. This behavior can be determined colorimetrically according to ISO 7724-3-1984.
  • This neutral evening color should also remain unchanged in the aftertreatment of the dyed textile goods with finishing agents known per se, for example silicone oils, such as amino-functional polysiloxanes.
  • R 1 radicals are, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl or 2-hydroxyethylsulfonyl.
  • R 6 and R 7 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, 2-hydroxyethyl, 2- or 3-hydroxypropyl, 2- or 4-hydroxybutyl, 2-phenoxyethyl, 2- or 3 -Phenoxypropyl, 2- (2-cyanoethoxy) ethyl, 2-acetyloxyethyl, 2-phenoxyacetyloxyethyl, 2-benzoyloxyethyl, 2-methoxycarbonyloxyethyl, 2-phenylaminocarbonyloxyethyl or 2-cyanoethyl.
  • R 2 and R 3 are each hydrogen or chlorine
  • R 4 is hydrogen or chlorine
  • R 5 is hydrogen
  • R 6 and R 7 independently of one another hydrogen, phenyl, C 1 -C 4 -alkyl or ethyl substituted by hydroxy, phenoxy, 2-cyanoethoxy, acetyloxy, phenoxyacetyloxy, benzoyloxy, methoxycarbonyloxy, phenylaminocarbonyloxy or cyano
  • Dye preparations containing up to 5% by weight, preferably up to 3% by weight and in particular 1 to 3% by weight, based in each case on the total weight of the dyes, of at least one azo dye of the formula V, in which Z 1 especially chlorine. Mixtures containing at least one azo dye of the formula III and / or IV and V are to be emphasized, these azo dyes having the following substituent pattern.
  • mixtures containing at least one azo dye of the formula Illd, Ulk and / or IVb and Vb are particularly noteworthy.
  • Advantageous dye mixtures are those that are 70 to
  • the new dye mixtures each contain, based on the total weight of the dyes, a) 10 to 20% by weight, preferably 12 to 17% by weight, of at least one azo dye of the formula I, b) 30 to 80% by weight, preferably 30 to 55% by weight of the azo dye of the formula Ha and optionally of the formula IIb, c) 25 to 50% by weight, preferably 30 to 50% by weight, of at least one azo dye of the formula III and / or IV and d) 0 to 5% by weight, preferably 1 to 3% by weight, of at least one azo dye of the formula V, with the proviso that the sum of the dyes mentioned under a), b), c) and d) is 100 Wt .-% results.
  • the dyes of the formula I, Ha, Ilb, III, IV and V are generally known dyes. They are e.g. from DE-A-2 818 653, DE-A-3 112 427, EP-A-64 221, US-A 5 283 326 or from K. Venkataraman "The Chemistry of Synthetic Dyes', Vol. III, pages 444 to 447, Academic Press, New York, London, 1970, or can be obtained by the methods mentioned there.
  • the dye mixtures according to the invention are prepared in a manner known per se, e.g. by mixing the respective partners in the weight ratio mentioned. If necessary, further components, e.g. Dispersants, such as lignin sulfonates or sulfonation products of the reaction product of formaldehyde with aromatics, or other auxiliaries, can be added. It is also possible to see already finished dye preparations from the respective partners or finished dye preparations with pure dyes.
  • Dispersants such as lignin sulfonates or sulfonation products of the reaction product of formaldehyde with aromatics, or other auxiliaries
  • the present invention further relates to dye preparations containing 15 to 60% by weight, based on the weight of the dye preparation, of a dye mixture described in more detail at the outset, and 40 to 85% by weight, based on the weight of the dye preparation, of dispersant .
  • the new dye mixtures are suitable for dyeing polyester in textile form.
  • these include textile forms, such as fibers, threads, threads, knitted fabrics, woven goods or Non-wovens, polyester or blended polyester with cotton, wool, cellulose acetate or triacetate. Colorings are obtained in black shades.
  • the dyeing processes are known per se. Further details can also be found in the examples.
  • Another object of the present application is a process for dyeing polyester in textile form, which is characterized in that polyester is dyed in an aqueous liquor with the dye mixture specified in more detail above, and the dyed polyester is then, optionally after a reductive post-cleaning, treated with a silicone oil.
  • the coloring is usually carried out at a temperature of 90 to 15 140 ° C, with 120 to 135 ° C being particularly mentioned.
  • the pH is generally 2 to 7, preferably 3 to 5.
  • dyeing auxiliaries known per se may be present in the dye bath, e.g. Dispersant based on lignin sulfonates or condensation products of naphthalene sulfonic acid with formaldehyde.
  • the material to be dyed is then removed, washed, optionally subjected to a reductive aftertreatment known per se (e.g. with sodium dithionite) at 60 to 80 ° C. and drying, and then treated with a silicone oil.
  • a reductive aftertreatment known per se (e.g. with sodium dithionite) at 60 to 80 ° C. and drying, and then treated with a silicone oil.
  • the material to be dyed is padded in an aqueous liquor at about 20 to 30 ° C with a commercially available silicone oil, e.g. based on amino-30 alkylm-modified polysiloxanes, with a liquor absorption of 50 to 100%. This is followed by drying at 100 to 130 ° C and finally fixing at 160 to 260 ° C.
  • the dye mixtures according to the invention result in a strong coloration of 35 dyeings and have a neutral evening color. They also have excellent production properties.
  • Aftertreatment of the polyesters dyed with the dye mixtures according to the invention in textile form with finishing agents based on silicone oils results in an increase in the color strength, which can be 20 to 40% depending on the quality of the polyester used.
  • the textile goods treated in this way have the desired neutral evening color unchanged.
  • the dyed polyester fabric is then reductively cleaned by placing it in 200 ml of a liquor containing 5 ml / l for 15 minutes
  • polyester fabric is then padded with 40 g / l of a commercially available silicone oil based on an aminoalkyl-modified polysiloxane at a pH of 5 to 6.
  • the liquor absorption is 100%. It is dried for 3 minutes at 120 ° C. and treated
  • the dye preparation mentioned above each contained 40% by weight of dye mixture and 60% by weight of a dispersant based on lignin sulfonate, in each case based on the weight of the preparation.
  • the dye mixture was composed as indicated in the following table, the following dyes being used.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

L'invention concerne des mélanges de colorants contenant: a) un colorant azo de la formule (I), dans laquelle Hal désigne chlore ou brome, b) le colorant azo de la formule (II), dans laquelle L désigne allyle ou éventuellement hydrogène, c) un colorant azo de la formule (III) et/ou (IV) où les restes mentionnés correspondent à la définition données dans la description, ainsi que d) éventuellement un colorant azo de la formule (V) dans laquelle Z1 désigne chlore ou brome et Z2 désigne hydrogène ou méthoxy. L'invention concerne en outre des compositions colorantes contenant ces nouveaux mélanges de colorants, l'utilisation de ces nouveaux mélanges de colorants pour teindre des polyesters sous forme textile, ainsi qu'un procédé pour teindre des polyesters sous forme textile.
EP95937884A 1994-11-21 1995-11-09 Melanges de colorants azo pour teintes noires Withdrawn EP0793692A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19944441369 DE4441369A1 (de) 1994-11-21 1994-11-21 Mischungen von Azofarbstoffen für schwarze Farbtöne
DE4441369 1994-11-21
PCT/EP1995/004405 WO1996016129A1 (fr) 1994-11-21 1995-11-09 Melanges de colorants azo pour teintes noires

Publications (1)

Publication Number Publication Date
EP0793692A1 true EP0793692A1 (fr) 1997-09-10

Family

ID=6533751

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95937884A Withdrawn EP0793692A1 (fr) 1994-11-21 1995-11-09 Melanges de colorants azo pour teintes noires

Country Status (4)

Country Link
EP (1) EP0793692A1 (fr)
JP (1) JPH10508896A (fr)
DE (1) DE4441369A1 (fr)
WO (1) WO1996016129A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3806166B2 (ja) * 1995-10-18 2006-08-09 ダイスタージャパン株式会社 青色系分散染料混合物及びその製造方法
CH693506A5 (de) * 1999-02-01 2003-09-15 Ciba Sc Holding Ag Farbstoffmischungen und ihre Verwendung zum Färben oder Bedrucken von Celluloseacetat enthaltenden Fasermaterialien.
DE10115281A1 (de) * 2001-03-28 2002-10-24 Infineon Technologies Ag Verfahren zur Overlayeinstellung zweier Maskenebenen bei einem photolithographischen Prozess zur Herstellung einer integrierten Schaltung
CN104087010B (zh) * 2013-05-16 2016-06-01 上海安诺其集团股份有限公司 一种分散染料混合物
CN104087017B (zh) * 2013-05-16 2016-05-25 上海安诺其集团股份有限公司 一种橙色分散染料的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3142609A1 (de) * 1981-10-28 1983-05-05 Basf Ag, 6700 Ludwigshafen Marineblaue dispersionsfarbstoffmischungen
JPH0244337B2 (ja) * 1983-07-22 1990-10-03 Mitsui Toatsu Chemicals Mizufuyoseibunsansenryososeibutsuoyobikoreomochiitahoriesuteruseninosenshokumatahanatsusenho
DE3734586A1 (de) * 1987-10-13 1989-05-03 Basf Ag Marineblaue und schwarze farbstoffmischungen
DE4232558A1 (de) * 1992-09-29 1994-03-31 Basf Ag Mischungen von Azofarbstoffen für marineblaue bis schwarze Farbtöne

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9616129A1 *

Also Published As

Publication number Publication date
DE4441369A1 (de) 1996-05-23
WO1996016129A1 (fr) 1996-05-30
JPH10508896A (ja) 1998-09-02

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