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EP0848734A1 - Mischungen von reaktiven disazofarbstoffen - Google Patents

Mischungen von reaktiven disazofarbstoffen

Info

Publication number
EP0848734A1
EP0848734A1 EP96924061A EP96924061A EP0848734A1 EP 0848734 A1 EP0848734 A1 EP 0848734A1 EP 96924061 A EP96924061 A EP 96924061A EP 96924061 A EP96924061 A EP 96924061A EP 0848734 A1 EP0848734 A1 EP 0848734A1
Authority
EP
European Patent Office
Prior art keywords
dye
sulpho
formula
composition according
parts
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Withdrawn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
EP96924061A
Other languages
English (en)
French (fr)
Inventor
John Anthony Taylor
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.)
Avecia Ltd
Original Assignee
Zeneca Ltd
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 Zeneca Ltd filed Critical Zeneca Ltd
Publication of EP0848734A1 publication Critical patent/EP0848734A1/de
Withdrawn legal-status Critical Current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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
    • C09B62/08—Azo dyes
    • C09B62/09—Disazo or polyazo dyes
    • 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
    • C09B67/0055—Mixtures of two or more disazo dyes
    • C09B67/0057—Mixtures of two or more reactive disazo dyes
    • C09B67/0058—Mixtures of two or more reactive disazo dyes all the reactive groups are directly attached to a heterocyclic system

Definitions

  • This invention relates to mixtures of reactive dyes, their preparation and use.
  • Reactive dyes and their use for the coloration of substrates have been known for about forty years. More recently, liquid brands of reactive dyes have become popular, particularly for the printing of textiles. There is a need for a green reactive dye which has a high build-up, and good solubility in aqueous media.
  • composition comprising a first, second, third and fourth dye, each of which is of formula (1) or a salt thereof:
  • X is a labile atom or group
  • a and B are each independently an optionally substituted phenylene group; one of R 1 and R 2 is H and the other is sulpho; one of R 3 and R 4 is H and the other is sulpho;
  • R 5 and R 6 are each independently C ⁇ . 4 -alkyl; and the first, second, third and fourth dye are different from each other.
  • X is preferably a quaternary ammonium group or halo, more preferably 3- or 4- carboxypyridinium, F or CI, especially Cl.
  • a and B are each independently sulphophenylene, more preferably sulpho-1 ,4-phenylene or sulpho-1 ,3-phenylene, especially sulpho-1 ,4-phenylene.
  • a and B are identical to each other.
  • R 5 and R 6 are preferably methyl.
  • the first dye is of the formula (2):
  • R 1 and R 3 are H and R 2 and R 4 are sulpho.
  • the second dye is preferably of formula (2) wherein R 1 and R 3 are sulpho and R 2 and R 4 are H.
  • the third dye is preferably of formula (2) wherein R 1 and R 4 are H and R 2 and R 3 are sulpho.
  • the fourth dye is preferably of formula (2) wherein R 1 and R 4 are sulpho and R 2 and R 3 are H.
  • the first, second, third and fourth dye each independently constitute 10 to 40 parts, more preferably 15 to 35 parts, especially 20 to 30 parts, more especially approximately 25 parts by weight in each 100 parts in total of the first, second, third and fourth dye.
  • compositions according to the invention can be prepared by condensing a compound of formula (3) wherein A and B are as hereinbefore defined with a mixture of first and second compound of formula (4) wherein R 6 is as hereinbefore defined, and R 7 is H and R 8 is sulpho in the first compound and R 7 is sulpho and R 8 is H in the second compound.
  • R 6 is as hereinbefore defined
  • R 7 is H
  • R 8 is sulpho in the first compound
  • R 7 is sulpho and R 8 is H in the second compound.
  • halo groups in the resultant composition can be replaced by quaternary ammonium groups by methods known in the art.
  • the condensation is preferably performed at a pH in the range 4 to 8, more preferably 5 to 7. A temperature of 20 to 50°C is convenient. Normally the condensation is performed in water or an aqueous solvent.
  • Compounds of formula (3) can be prepared by diazotising nitroamines of formula H 2 N-A-NO 2 and H2N-B-NO2 (wherein A and B are as hereinbefore defined) and coupling the resultant diazonium salts onto 1-amino-8-hydroxynaphthalene-3,6-disulphonic acid and reducing the resulting dinitro compound to give a compound of Formula (3).
  • Diazotisation is normally performed below 5°C using NaNO 2 and dilute mineral acid.
  • Compounds and mixtures of formula (4) may be prepared by condensing a cyanuric halide with appropriate aniline derivatives.
  • the dyes in the composition are preferably in the form of their sodium, potassium or lithium salt, or a mixed salt thereof.
  • compositions according to the invention are useful for the preparation of high strength liquid dyes.
  • a further feature of the invention provides a liquid dye comprising water and up to 30 parts, preferably 1 to 30 parts, more preferably 10 to 20 parts, of a composition according to the invention in each
  • the liquid dye may also contain solubility enhancing agents, e.g. urea, which assists strength and stability of the liquid dyes.
  • the present invention also provides a process for colouring a substrate comprising applying thereto a composition according to the invention, preferably as a solution in water.
  • the substrate is preferably a leather or a textile material having -OH or -NH- groups, for example wool, silk, polyamide and especially cellulosic materials e.g. cotton.
  • the composition is preferably applied to cellulosic materials in conjunction with an acid binding agent, for example an alkali metal hydroxide, carbonate or bicarbonate.
  • compositions of the invention colour textiles an attractive green shade and benefit from high solubility in aqueous media.
  • This allows high strength solutions to be prepared and gives good storage stability to solutions of normal strength.
  • the dyes have good dyeing properties, high substantivity high solubility and compatibility with other PROCION H-EXL dyes. This compatibility allows binary and tertiary mixtures to be made which give consistent dyeings over a variety of different dyeing conditions.
  • Example 1 The invention is further illustrated by the following examples.
  • Example 1 The invention is further illustrated by the following examples.
  • a dyebase of the formula (5) was prepared by following the exemplified method of GB 1 ,387,925 (See page 2, lines 10 - 30).
  • Example 2 The mixture from Example 1 , stage b) and Dyes A and B from Example 1 were applied to cotton at 1%,2%,4%,6% and 9% by exhaust dyeing. The build up was measured by assessing the strength of the dyeing on cotton by reflectance spectroscopy. The mixture was found to build up better than A and B alone at 1%, 2%, 4%, 6% and 9%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
EP96924061A 1995-08-26 1996-07-12 Mischungen von reaktiven disazofarbstoffen Withdrawn EP0848734A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9517570.9A GB9517570D0 (en) 1995-08-26 1995-08-26 Mixtures
GB9517570 1995-08-26
PCT/GB1996/001665 WO1997008246A1 (en) 1995-08-26 1996-07-12 Mixtures of disazo reactive dyes

Publications (1)

Publication Number Publication Date
EP0848734A1 true EP0848734A1 (de) 1998-06-24

Family

ID=10779853

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96924061A Withdrawn EP0848734A1 (de) 1995-08-26 1996-07-12 Mischungen von reaktiven disazofarbstoffen

Country Status (5)

Country Link
EP (1) EP0848734A1 (de)
JP (1) JPH11511494A (de)
AU (1) AU6464296A (de)
GB (1) GB9517570D0 (de)
WO (1) WO1997008246A1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9608487D0 (en) * 1996-04-25 1996-07-03 Zeneca Ltd Compositions, processes and uses
GB0411589D0 (en) * 2004-05-24 2004-06-23 Dystar Textilfarben Gmbh & Co Mixtures of fibre reactive azo dyes
CN115466524B (zh) * 2022-09-02 2024-07-23 浙江劲光实业股份有限公司 一种活性染料的合成方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5331732A (en) * 1976-09-06 1978-03-25 Nippon Kayaku Co Ltd Preparation of bisazo dye
JPS53117024A (en) * 1977-03-24 1978-10-13 Nippon Kayaku Co Ltd Bis-azo compounds, their preparation, and dyeing of cellulosic fibrous materials with them
CH672794A5 (en) * 1982-04-27 1989-12-29 Nippon Kayaku Kk Reactive dis:azo dyestuff cpds.
DE3325788A1 (de) * 1983-03-15 1984-09-20 Bayer Ag, 5090 Leverkusen Faserreaktive disazofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben oder bedrucken von stubstraten
JPS6090265A (ja) * 1983-10-25 1985-05-21 Nippon Kayaku Co Ltd ジスアゾ化合物の製造法
DE3923483A1 (de) * 1989-07-15 1991-01-24 Sandoz Ag Faserreaktive disazofarbstoffe

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9708246A1 *

Also Published As

Publication number Publication date
JPH11511494A (ja) 1999-10-05
GB9517570D0 (en) 1995-11-01
AU6464296A (en) 1997-03-19
WO1997008246A1 (en) 1997-03-06

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Legal Events

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