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WO1999013008A1 - Colorants disazoiques solubles dans l'eau et encres pour procede d'impression par jets d'encre contenant ces colorants - Google Patents

Colorants disazoiques solubles dans l'eau et encres pour procede d'impression par jets d'encre contenant ces colorants Download PDF

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Publication number
WO1999013008A1
WO1999013008A1 PCT/GB1998/002522 GB9802522W WO9913008A1 WO 1999013008 A1 WO1999013008 A1 WO 1999013008A1 GB 9802522 W GB9802522 W GB 9802522W WO 9913008 A1 WO9913008 A1 WO 9913008A1
Authority
WO
WIPO (PCT)
Prior art keywords
ink
dye
compound
water
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.)
Ceased
Application number
PCT/GB1998/002522
Other languages
English (en)
Inventor
Paul Wight
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
Syngenta Ltd
Original Assignee
Zeneca Ltd
Avecia 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
Priority claimed from GBGB9719011.0A external-priority patent/GB9719011D0/en
Priority claimed from GBGB9726340.4A external-priority patent/GB9726340D0/en
Application filed by Zeneca Ltd, Avecia Ltd filed Critical Zeneca Ltd
Priority to GB0003801A priority Critical patent/GB2346151B/en
Priority to AU88694/98A priority patent/AU8869498A/en
Publication of WO1999013008A1 publication Critical patent/WO1999013008A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • 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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
    • 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
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye

Definitions

  • This invention relates to dyes, to inks and to their use in ink jet printing ("UP").
  • UP is a non-impact printing technique in which droplets of ink are ejected through a fine nozzle onto a substrate without bringing the nozzle into contact with the substrate.
  • the inks are often required to dry quickly when applied to a substrate to prevent smudging, but they should not form a crust over the tip of an ink jet nozzle because this will stop the printer from working.
  • the inks should also be stable to storage over time without decomposing or forming a precipitate which could block the fine nozzle.
  • n has a value of 1 or 2; and R 1 is methyl or ethyl.
  • n has a value of 1 because the resultant compounds can be used to make ink jet printing inks having particularly good properties.
  • the carboxy group shown in Formula (1) is preferably at the 4- position.
  • the carboxy groups shown in Formula (1) are preferably at the 3- and 5- positions.
  • R 1 is preferably methyl.
  • the dyes of Formula (1) may be prepared by diazotising a compound of the
  • the diazotisation is preferably performed at a temperature below 6°C, more preferably at a temperature in the range -10°C to 5°C.
  • the diazotisation is performed in water, preferably at a pH below 7.
  • Dilute mineral acid eg HCI or H 2 SO 4 , are often used to achieve the desired acidic conditions.
  • the compound of Formula (2) may be prepared by diazotising mono or dicarboxy aniline to give a diazonium salt and coupling this diazonium salt with 2-(methoxy or ethoxy)-5-methyl aniline.
  • Preferred salts are alkali metal salts, especially lithium, sodium and potassium salts, ammonium and substituted ammonium salts. Especially preferred salts are salts with ammonia and volatile amines.
  • the dyes may be converted into a salt using known techniques. For example, an alkali metal salt of a dye may be converted into a salt with ammonia or an amine by dissolving an alkali metal salt of the dye in water, acidifying with a mineral acid and adjusting the pH of the solution to pH 9 to 9.5 with ammonia or the amine and removing the alkali metal cations by dialysis.
  • the dyes may exist in tautomeric forms other than those shown in this specification. These tautomers are included within the scope of the present claims.
  • an ink comprising: (a) from 0.01 to 30 parts of a compound of the Formula (1 );
  • the number of parts of component (a) is preferably from 0.1 to 20, more preferably from 0.5 to 15, and especially from 1 to 5 parts.
  • the number of parts of component (b) is preferably from 99.9 to 80, more preferably from 99.5 to 85, especially from 99 to 95 parts.
  • component (a) When the medium is a liquid, preferably component (a) is completely dissolved in component (b).
  • component (a) has a solubility in component (b) at 20°C of at least 10%. This allows the preparation of concentrates which may be used to prepare more dilute inks and reduces the chance of the dye precipitating if evaporation of the liquid medium occurs during storage.
  • Preferred liquid media include water, a mixture of water and an organic solvent and an organic solvent free from water.
  • the weight ratio of water to organic solvent is preferably from 99:1 to 1 :99, more preferably from 99:1 to 50:50 and especially from 95:5 to 80:20.
  • the organic solvent present in the mixture of water and organic solvent is a water-miscible organic solvent or a mixture of such solvents.
  • Preferred water- miscible organic solvents include C ⁇ -alkanols, preferably methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, n-pentanol, cyclopentanol and cyclohexanol; linear amides, preferably dimethylformamide or dimethylacetamide; ketones and ketone-alcohols, preferably acetone, methyl ether ketone, cyclohexanone and diacetone alcohol; water-miscible ethers, preferably tetrahydrofuran and dioxane; diols, preferably diols having from 2 to 12 carbon atoms, for example pentane-1 ,5-diol, ethylene glycol
  • Especially preferred water-soluble organic solvents are cyclic amides, especially 2- pyrrolidone, N-methyl-pyrrolidone and N-ethyl-pyrrolidone; diols, especially 1 ,5-pentane diol, ethyleneglycol, thiodiglycol, diethyleneglycol and triethyleneglycol; and mono- C M -alkyl and C 1-4 -al yl ethers of diols, more preferably mono- C 1-4 -alkyl ethers of diols having 2 to 12 carbon atoms, especially 2-methoxy-2-ethoxy-2-ethoxyethanol.
  • a preferred liquid medium comprises:
  • Another preferred liquid medium comprises: (a) from 60 to 80 parts water; (b) from 2 to 20 parts diethylene glycol; and
  • the solvent preferably has a boiling point of from 30° to 200°C, more preferably of from 40° to 150°C, especially from 50 to 125°C.
  • the organic solvent may be water-immiscible, water-miscible or a mixture of such solvents.
  • Preferred water- miscible organic solvents are any of the hereinbefore described water-miscible organic solvents and mixtures thereof.
  • Preferred water-immiscible solvents include, for example, aliphatic hydrocarbons; esters, preferably ethyl acetate; chlorinated hydrocarbons, preferably CH 2 CI 2 ; and ethers, preferably diethyl ether; and mixtures thereof.
  • the liquid medium comprises a water-immiscible organic solvent
  • a polar solvent is included because this enhances solubility of the dye in the liquid medium.
  • polar solvents include C,. 4 -alcohols.
  • the liquid medium is an organic solvent free from water it comprises a ketone (especially methyl ethyl ketone) &/or an alcohol (especially a C 1-4 -alkanol, more especially ethanol or propanol).
  • the organic solvent free from water may be a single organic solvent or a mixture of two or more organic solvents. It is preferred that when the medium is an organic solvent free from water it is a mixture of 2 to 5 different organic solvents.
  • Ink media comprising an organic solvent free from water are particularly useful where fast drying times are required and particularly when printing onto hydrophobic and non-absorbent substrates, for example plastics, metal and glass.
  • Preferred low melting solid media have a melting point in the range from 60°C to 125°C.
  • Suitable low melting point solids include long chain fatty acids or alcohols, preferably those with C 18 . 24 chains, and sulphonamides.
  • the dye of Formula (1) may be dissolved in the low melting point solid or may be finely dispersed in it.
  • the ink may also contain additional components (i.e. components other than (a) and (b)) conventionally used in ink jet printing inks, for example viscosity and surface tension modifiers, corrosion inhibitors, biocides, kogation reducing additives and surfactants which may be ionic or non-ionic.
  • additional components i.e. components other than (a) and (b)
  • viscosity and surface tension modifiers for example viscosity and surface tension modifiers, corrosion inhibitors, biocides, kogation reducing additives and surfactants which may be ionic or non-ionic.
  • Inks of the invention benefit from an attractive, neutral black shade. They have good solubility in aqueous media, produce images of high optical density, have high light- fastness and are relatively inexpensive.
  • Suitable additional colorants include: yellow dyes, preferably C.I. Direct Yellow 86, 132, 142, 144 and 173, C.I. Reactive Yellow 85, C.I. Reactive yellow 135 and C.I.Acid Yellow 23; Cyan dyes, preferably C.I.Acid Blue 9, C.I. Direct Blue 199, C.I.
  • Direct Blue 307 and C.I. Reactive Blue 71 magenta dyes, preferably C.I.Acid Red 52 and 249 and C.I. Direct Violet 106 and 107; Black dyes, preferably C.I. Direct Black 195, 168 and 19, C.I. Reactive Black 31, C.I. Food Black 2 and dyes of Formula (I) and (II) described in European Patent Application No. 96113585.2 which are incorporated herein by reference thereto.
  • C.I. Direct Yellow 86 the most preferred are C.I. Direct Yellow 86,
  • the inks contain a further dye this is preferably present in an amount of 2 to 50%, more preferably 5 to 25% by weight relative to the amount of dye of Formula (1).
  • inks of the invention contain a dye of Formula (1) described herein as the sole colorant.
  • a further aspect of the invention provides a process for printing an image on a substrate comprising applying an ink containing a compound of Formula (1) to the substrate by means of an ink jet printer.
  • the ink used in this process is preferably as defined in the second aspect of the present invention.
  • the ink jet printer preferably applies the ink to the substrate in the form of droplets which are ejected through a small orifice onto the substrate.
  • Preferred ink jet printers are piezoelectric ink jet printers and thermal ink jet printers.
  • thermal ink jet printers programmed pulses of heat are applied to the ink in a reservoir by means of a resistor adjacent to the orifice, thereby causing the ink to be ejected in the form of small droplets directed towards the substrate during relative movement between the substrate and the orifice.
  • piezoelectric ink jet printers the oscillation of a small crystal causes ejection of the ink from the orifice.
  • the substrate is preferably paper, plastic, a textile, metal or glass, more preferably paper, an overhead projector slide or a textile material, especially paper.
  • Preferred papers are plain or treated papers which may have an acid, alkaline or neutral character. Examples of commercially available treated papers include Seiko Epson coated paper, Seiko Epson Glossy paper, Hewlett-Packard Glossy paper and Canon HR101 paper.
  • a further aspect of the present invention provides a paper, an overhead projector slide or a textile material printed with an ink, a dye or by means of a process as hereinbefore defined.
  • the ink according to the invention is preferably applied thereto by: i) applying the ink to the textile material using an ink jet printer; and ii) heating the printed textile material at a temperature of from 50°C to 250°C.
  • Preferred textile materials are natural, synthetic and semi-synthetic materials.
  • Examples of preferred natural textile materials include wool, silk, hair and cellulosic materials, particularly cotton, jute, hemp, flax and linen.
  • Examples of preferred synthetic and semi-synthetic materials include polyamides, polyesters, polyacrylonitriles and polyurethanes.
  • the textile material has been treated with an aqueous pre-treatment composition comprising a thickening agent and optionally a water-soluble base and a hydrotropic agent and dried prior to step i) above.
  • the pre-treatment composition preferably comprises a solution of the base and the hydrotropic agent in water containing the thickening agent. Particularly preferred pre- treatment compositions are described more fully in European Patent Application NO.534660A1.
  • a further feature of the invention comprises an ink jet printer cartridge containing an ink according to the present invention.
  • 4-aminobenzoic acid (27.4g) was stirred in water (1 litre) and acidified using cone.
  • stage 1 The product from stage 1 (57. Og) was suspended in water (800ml). The thick mixture was cooled to 0-10°C and sodium nitrite (33.1g) was added. Concentrated HCI (75ml) was added with stirring at 0-10°C over about 10 minutes. Stirring and manual agitation at high speed and 30-33°C was continued for 1 hour to give a diazonium salt.
  • 1-hydroxy-3,6-disulpho-7-aminonaphthalene (79. Og) was suspended in water (700ml) and dissolved by the addition of sodium hydroxide solution to pH 9.5. The solution was cooled to 0-5°C and the diazonium salt was added over about 30 minutes at 0-10°C, maintaining the pH at 9-9.5 using 2M NaOH. After 1 1 /_ hours stirring, 10% NaCI solution (300g) was added and the pH adjusted to 3.6 using cone. HCI. The precipitate was filtered-off, washed with brine (15%, 400ml), slurhed with acetone (11), filtered off and washed with further acetone (500ml).
  • the resultant paste was dissolved in ammonia solution and re-precipitated using cone. HCI to pH3. After further purifications by precipitation, the precipitate was dissolved in dilute ammonia and dialysed to remove chloride ions. The solution was filtered through a GF/F filter, the liquid phase removed in vacuo and the product dried to give 69.4g of the title compound.
  • Example 2 Example 1 may be repeated except that in place of 2-methoxy-5-methyl aniline there is used 2-ethoxy-5-methyl aniline.
  • the inks described in Tables I and II may be prepared wherein the Dye described in the first column is the Dye made in the above example of the same number. Numbers quoted in the second column onwards refer to the number of parts of the relevant ingredient and all parts are by weight.
  • the inks may be applied to paper by thermal or piezo ink jet printing.
  • PG propylene glycol
  • DEG diethylene glycol
  • NMP N-methyl pyrollidone
  • D K dimethylketone
  • IPA isopropanol
  • TBT tertiary butanol
  • TDG thiodiglycol
  • Example 1 The method of Example 1 was repeated except that in place of 4-aminobenzoic acid there was used 2-amino benzoic acid.
  • Inks may be prepared as described in Tables I and II above except that in place of Dye 2 there is used the dye of this Example 16.
  • Example 1 The method of Example 1 was repeated except that in place of 4-aminobenzoic acid there was used 3-amino benzoic acid.
  • Inks may be prepared as described in Tables I and II above except that in place of Dye 1 there is used the dye of this Example 17.
  • Example 1 The method of Example 1 was repeated except that in place of 4-aminobenzoic acid there was used 3,5-dicarboxyaniline.
  • Inks may be prepared as described in Tables I and II above except that in place of

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)

Abstract

La présente invention concerne des composés représentés par la formule (1) ci-dessous, dans laquelle n est égal à 0 ou 1 et R1 est méthyle ou éthyle. Cette invention concerne également des encres contenant de tels composés, et un processus permettant d'imprimer une image en utilisant ces encres dans une imprimante à jets d'encre.
PCT/GB1998/002522 1997-09-09 1998-08-21 Colorants disazoiques solubles dans l'eau et encres pour procede d'impression par jets d'encre contenant ces colorants Ceased WO1999013008A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB0003801A GB2346151B (en) 1997-09-09 1998-08-21 Water soluble disazo dyestuffs as well as inks for ink jet recording method containing them
AU88694/98A AU8869498A (en) 1997-09-09 1998-08-21 Watersoluble disazo dyestuffs as well as inks for ink jet recording method containing them

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GBGB9719011.0A GB9719011D0 (en) 1997-09-09 1997-09-09 Compound
GB9719011.0 1997-09-09
GB9726340.4 1997-12-12
GBGB9726340.4A GB9726340D0 (en) 1997-12-12 1997-12-12 Compound

Publications (1)

Publication Number Publication Date
WO1999013008A1 true WO1999013008A1 (fr) 1999-03-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1998/002522 Ceased WO1999013008A1 (fr) 1997-09-09 1998-08-21 Colorants disazoiques solubles dans l'eau et encres pour procede d'impression par jets d'encre contenant ces colorants

Country Status (3)

Country Link
AU (1) AU8869498A (fr)
GB (1) GB2346151B (fr)
WO (1) WO1999013008A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0539178A2 (fr) * 1991-10-25 1993-04-28 Lexmark International, Inc. Colorant résistant à l'eau et encre aqueuse
WO1995031505A1 (fr) * 1994-05-18 1995-11-23 Zeneca Limited Compose disazo
WO1996013553A1 (fr) * 1994-10-28 1996-05-09 Zeneca Limited Colorant disaro
EP0771860A2 (fr) * 1995-11-02 1997-05-07 Seiko Epson Corporation Composition d'encre permettant une excellente réproduction du noir et procédé d'enregistrement par jet d'encre en faisant utilisation
GB2318124A (en) * 1996-10-11 1998-04-15 Zeneca Ltd Disazo dyes based on 7-(optionally substituted amino)-3-sulphonaphth-1-ol coupling component and their use in inkjet inks

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0539178A2 (fr) * 1991-10-25 1993-04-28 Lexmark International, Inc. Colorant résistant à l'eau et encre aqueuse
WO1995031505A1 (fr) * 1994-05-18 1995-11-23 Zeneca Limited Compose disazo
WO1996013553A1 (fr) * 1994-10-28 1996-05-09 Zeneca Limited Colorant disaro
EP0771860A2 (fr) * 1995-11-02 1997-05-07 Seiko Epson Corporation Composition d'encre permettant une excellente réproduction du noir et procédé d'enregistrement par jet d'encre en faisant utilisation
GB2318124A (en) * 1996-10-11 1998-04-15 Zeneca Ltd Disazo dyes based on 7-(optionally substituted amino)-3-sulphonaphth-1-ol coupling component and their use in inkjet inks

Also Published As

Publication number Publication date
GB0003801D0 (en) 2000-04-05
GB2346151B (en) 2002-04-10
AU8869498A (en) 1999-03-29
GB2346151A (en) 2000-08-02

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