WO2000037567A1 - Colorants azoiques - Google Patents

Colorants azoiques Download PDF

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Publication number
WO2000037567A1
WO2000037567A1 PCT/EP1999/009554 EP9909554W WO0037567A1 WO 2000037567 A1 WO2000037567 A1 WO 2000037567A1 EP 9909554 W EP9909554 W EP 9909554W WO 0037567 A1 WO0037567 A1 WO 0037567A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
hydrogen
acid
compounds
formula
Prior art date
Application number
PCT/EP1999/009554
Other languages
German (de)
English (en)
Inventor
Klaus Kunde
Michael-Thomas Jörss
Peter Wild
Original Assignee
Bayer Aktiengesellschaft
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 Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to EP99964525A priority Critical patent/EP1141139A1/fr
Priority to JP2000589629A priority patent/JP2002533519A/ja
Priority to AU30359/00A priority patent/AU3035900A/en
Publication of WO2000037567A1 publication Critical patent/WO2000037567A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues

Definitions

  • the invention relates to new azo dyes, a process for their preparation and their use for dyeing and printing paper and other materials, in particular as a dye in Ik jet inks.
  • the dyes according to the invention have the formula in the form of their free acids
  • R represents hydrogen or optionally substituted C ] -C 6 alkyl
  • R 1 denotes optionally substituted C 1 -C 6 -alkyl or optionally substituted phenyl
  • n 0 or 1
  • T 1 and T 2 independently of one another represent OR 5 , NR 6 R 7 or SR 8 ,
  • R 5 and R 8 independently of one another are hydrogen, Ci-Cg-alkyl, C 2 -C 6 -alkyl substituted by sulfo, carboxy, and / or di-Ct-C -alkylamino or phenyl optionally substituted by C r C 4 alkyl, C r C 4 alkoxy, sulfo, F, Br and / or Cl,
  • R 6 are hydrogen, C 6 alkyl or optionally substituted by sulfo, hydroxy, C r C 3 - alkoxy, amino or mono- or di-C ⁇ -C3-alkylamino-substituted C 2 -C 6 alkyl,
  • R 7 independently of R 6 has the meaning of R 6 or optionally substituted by C r C 4 alkyl, -CC alkoxy, carboxy, sulfo, F, Cl and / or Br is phenyl or naphthyl or
  • R 6 and R 7 together with the N-atom to which they are attached form a morpholine radical or an unsubstituted or substituted by Cj-C 4 alkyl, C 2 -C 4 hydroxyalkyl or C2-C4-aminoalkyl-substituted piperazine .
  • substituents for optionally substituted alkyl radicals are, for example: OH, NR 3 R 4 , where R 3 and R 4 are independently of one another
  • substituents for optionally substituted phenyl are, for example: C r C 6 alkyl, C r C 6 alkoxy, COOH, SO 3 H, F, Cl, Br.
  • Preferred dyes of the formula (I) are those in which
  • R represents hydrogen, C, -C 6 alkyl or C 2 -C 4 hydroxyalkyl
  • R 1 C j -C 6 alkyl, C 2 -C 4 hydroxyalkyl, C 2 -C 4 aminoalkyl, in particular C 2 -C 4 alkyl substituted by NR 3 R 4 , wherein R 3 and R 4 independently of one another represent hydrogen, C j -C 4 alkyl and C 2 -C 4 hydroxyalkyl, or optionally by C r C alkyl, C r C alkoxy, COOH, SO3H, F, Cl and / or Br is substituted phenyl and
  • T 1 and T 2 have the meaning given above.
  • R, R 1 , T 1 , T 2 and m have the meanings given above.
  • R 1 preferably denotes CH 3 , C 2 H 5 , C 3 H 7 , C 2 H 4 OH, C 2 H 4 SO 3 H, C 3 H 6 OH, C 3 H 6 SO 3 H, C 2 H 4 COOH , C 3 H 6 COOH, C 6 H 5 , C 6 H 4 SO 3 H, C 6 H 4 COOH or C 2 H 4 N (CH 3 ) 2 ,
  • R is preferably hydrogen, CH 3 , C 2 H 5 or CH OH,
  • R 3 and R 4 independently of one another are preferably hydrogen, CH 3 or C 2 H 4 OH
  • R 5 is preferably derived from the following compounds H ⁇ R 5 : ethylene glycol, isethionic acid (2-hydroxyethanesulfonic acid) or water,
  • R 6 preferably denotes hydrogen, CH 3 , C 2 H 5 , C 3 H 7 , C 2 H 4 OH, C 2 H 4 OCH 3 or C 3 H 6 OH,
  • R 7 preferably denotes hydrogen, C 2 H 4 OH, C 3 H 6 OH, C 2 H 4 SO 3 H, C 2 H 4 COOH, C 3 H 6 SO 3 H, C 3 H 6 COOH, C 6 H 5 , C 6 H 4 SO 3 H, C 6 H 4 COOH or
  • R 6 and R 7 together with the N atom to which they are attached preferably form a radical of the formula
  • R 8 is preferably derived from the following thiols HSR 8 : 2-mercaptoethanol or 3-mercapto-1-propanesulfonic acid,
  • R 9 preferably denotes hydrogen, CH 3 or CH 4 OH
  • T 1 and T 2 are preferably derived independently of one another from the following amines Tinen and T 2 H:
  • R is hydrogen, CH 3 or C 2 H 5 ,
  • R 1 represents CH 3 , C 2 H 5 , C 3 H 7 , C 4 H 9 or C 6 H 5 and
  • T 1 and T 2 have the meanings given above, preferably for OH, NH 2 ,
  • the dyes of the formula (I) are preferably used in the form of their lithium, sodium, potassium or ammonium salts.
  • Particularly suitable ammonium salts are those in which 1 to 4 hydrogen atoms are replaced by identical or different Ci-Cg-alkyl groups or C 2 -Cg-alkyl groups substituted by hydroxyl or C 1 -C 3 -alkoxy groups.
  • Alkanolammonium salts such as methyldiethanolammonium, dimethylethanolammonium or triethanolammonium and quaternary ammonium ions such as tetramethylammonium or tetraethylammonium are particularly preferred.
  • the invention further relates to a process for the preparation of the compounds of the formula (I) according to the invention, which is characterized in that compounds of the formula (IV) wherein
  • the compounds of formula (IV) are described for example in DOS 30 22 972 or can be obtained in an analogous manner.
  • the conditions for the reaction of compounds of formula (IV) with 2,4,6-trifluoro or 2,4,6-trichloro-1,3,5-triazine are also known (for example DE-A 29 35 681 , EP-65 479).
  • the compounds of formula (I) according to the invention can be used as solid or liquid dye preparations. They are preferably used in the form of aqueous preparations, especially solutions. These aqueous dye preparations generally contain one or more dyes of the formula (I), optionally suitable organic solvents, including hydrotropic compounds, and further auxiliaries and / or stabilizers. It is advantageous to prepare the aqueous dye solutions in the course of the dye synthesis itself, without intermediate isolation of the dye.
  • aqueous dye preparations are particularly preferred when dyeing or printing paper.
  • a stable, aqueous, concentrated dyeing preparation can be prepared in a general manner by dissolving the
  • Dye in water optionally with the addition of one or more auxiliaries, e.g. a hydrotropic compound or a stabilizer.
  • auxiliaries e.g. a hydrotropic compound or a stabilizer.
  • the aqueous dye preparations generally contain about 0.5 to 20% by weight of one or more dyes of the formula (I) and 80 to 99.5% by weight
  • Preferred organic solvents are alcohols and their ethers or esters, carboxamides, ureas, sulfoxides and sulfones, especially those with molecular weights ⁇ 200 g / mol.
  • Particularly suitable solvents are, for example: methanol, ethanol, propanol; Ethylene, propylene, diethylene, thio-diethylene and dipropylene glycol; Butanediol; ß-hydroxypropionitrile, pentamethylene glycol, ethylene glycol monoethyl and propyl ether, ethylene diglycol monoethyl ether, triethylene glycol monobutyl ether, butyl polyglycol, formamide, triethylene glycol, 1,5-pentanediol, 1,3,6-hexanetriol, 2-hydroxyethyl acetic acid (2'-ethyl acetate, acetic acid 2-ethyl acetate, hydroxy) ethyl ester
  • Suitable additives for aqueous dye preparations are those ionic or nonionic substances with which the viscosity and / or surface tension can be adjusted to the ranges required for the application, such as anionic, cationic or neutral surfactants such as dispersants and Viscosity regulators.
  • anionic, cationic or neutral surfactants such as dispersants and Viscosity regulators.
  • Viscosity regulators can, for example, be adopted from organic solvents.
  • Aqueous dye preparations in particular dye solutions, are preferred.
  • the aqueous dye preparations can by dissolving the dye salts in water or from the condensation solutions, which are optionally subjected to isomer exchange and / or desalination, for example by pressure permeation and / or by adding one or more of the above-mentioned organic solvents, if appropriate at elevated temperatures (30 to 100 ° C, in particular 30 to 50 ° C) and with the addition of inorganic and organic bases; if appropriate, conventional ionic or nonionic additives can also be used, for example those with which the viscosity can be reduced and / or the surface tension can be increased.
  • the corresponding free acids can also be used in combination with at least equimolar amounts of the corresponding organic or organic bases.
  • aqueous dye preparations according to the invention are also suitable for
  • Production of printing inks which can also be used in particular as recording liquids according to the ink jet method.
  • Another object of the invention is therefore printing inks containing at least one dye (I) and their use as recording liquid for ink
  • the ink jet method of the method according to the invention is understood to mean an ink jet recording method in which the ink drops are sprayed onto the substrate.
  • the fine ink droplets can be produced by different methods. They are preferably produced using the generally known thermal jet, bubble jet, piezo jet or valve ink jet processes.
  • Recording systems have the following advantages: The physical properties properties such as viscosity, surface tension and the like are in the appropriate ranges; the recording liquid does not cause clogging in fine discharge ports of ink jet recorders; it provides high density images; during storage there is no change in physical and physical properties in the recording liquid
  • the recording liquid is suitable for recording on various recording media without restrictions on the type of recording media; finally, the recording liquid fixes quickly and results in images with excellent water resistance, light fastness, abrasion resistance and resolution.
  • the dyeings or prints obtained with the dyes according to the invention in particular the prints which were obtained on paper by the inkjet method, have excellent wet fastness properties.
  • E ⁇ value standardized absorbance of a 1% solution (water) with a layer thickness of 1 cm.
  • Example 2 10 g of the concentrated solution from Example 1 are stirred with 70 g of water and 20 g of 1,5-pentanediol. An ink is obtained which, when printed with a commercially available ink jet printer, delivers red, brilliant, light-fast records on commercially available paper.
  • 1,3,5-triazine can be used.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet (AREA)

Abstract

L'invention concerne des composés ayant, dans leur forme d'acides libres, la formule (I) où les substituants ont la signification figurant dans la description. Ces substituants sont particulièrement adaptés comme colorants d'encres destinées à l'impression par jet d'encre.
PCT/EP1999/009554 1998-12-18 1999-12-07 Colorants azoiques WO2000037567A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP99964525A EP1141139A1 (fr) 1998-12-18 1999-12-07 Colorants azoiques
JP2000589629A JP2002533519A (ja) 1998-12-18 1999-12-07 アゾ染料
AU30359/00A AU3035900A (en) 1998-12-18 1999-12-07 Azo dyes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19858730.9 1998-12-18
DE19858730A DE19858730A1 (de) 1998-12-18 1998-12-18 Azofarbstoffe

Publications (1)

Publication Number Publication Date
WO2000037567A1 true WO2000037567A1 (fr) 2000-06-29

Family

ID=7891743

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/009554 WO2000037567A1 (fr) 1998-12-18 1999-12-07 Colorants azoiques

Country Status (5)

Country Link
EP (1) EP1141139A1 (fr)
JP (1) JP2002533519A (fr)
AU (1) AU3035900A (fr)
DE (1) DE19858730A1 (fr)
WO (1) WO2000037567A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1449894A2 (fr) * 2002-01-25 2004-08-25 Hewlett-Packard Company Structure de colorant pour l'impression par jet d'encre

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3022927A1 (de) * 1979-06-26 1981-01-22 Sandoz Ag Faserreaktive monoazoverbindungen, verfahren zur herstellung und verwendung
WO1996024636A1 (fr) * 1995-02-07 1996-08-15 Ilford A.G. Colorants pour imprimantes a jet d'encre
EP0755984A1 (fr) * 1995-07-26 1997-01-29 Ilford Ag Colorants pour impression par jet d'encre
EP0794233A1 (fr) * 1996-03-04 1997-09-10 Ciba SC Holding AG Colorants acides anioniques, procédé pour leur fabrication et leur utilisation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3022927A1 (de) * 1979-06-26 1981-01-22 Sandoz Ag Faserreaktive monoazoverbindungen, verfahren zur herstellung und verwendung
WO1996024636A1 (fr) * 1995-02-07 1996-08-15 Ilford A.G. Colorants pour imprimantes a jet d'encre
EP0755984A1 (fr) * 1995-07-26 1997-01-29 Ilford Ag Colorants pour impression par jet d'encre
EP0794233A1 (fr) * 1996-03-04 1997-09-10 Ciba SC Holding AG Colorants acides anioniques, procédé pour leur fabrication et leur utilisation

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1449894A2 (fr) * 2002-01-25 2004-08-25 Hewlett-Packard Company Structure de colorant pour l'impression par jet d'encre
EP1449894A3 (fr) * 2002-01-25 2004-10-20 Hewlett-Packard Company Structure de colorant pour l'impression par jet d'encre
US7407541B2 (en) 2002-01-25 2008-08-05 Hewlett-Packard Development Company, L.P. Inkjet dye design
US7449057B2 (en) 2002-01-25 2008-11-11 Hewlett-Packard Development Company, L.P. Ink jet dye design
US8119777B2 (en) 2002-01-25 2012-02-21 Hewlett-Packard Development Company, L.P. Ink jet dye design

Also Published As

Publication number Publication date
DE19858730A1 (de) 2000-06-21
JP2002533519A (ja) 2002-10-08
EP1141139A1 (fr) 2001-10-10
AU3035900A (en) 2000-07-12

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