WO2004011561A1 - Encre - Google Patents

Encre Download PDF

Info

Publication number
WO2004011561A1
WO2004011561A1 PCT/GB2003/002117 GB0302117W WO2004011561A1 WO 2004011561 A1 WO2004011561 A1 WO 2004011561A1 GB 0302117 W GB0302117 W GB 0302117W WO 2004011561 A1 WO2004011561 A1 WO 2004011561A1
Authority
WO
WIPO (PCT)
Prior art keywords
ink
water
ink jet
parts
organic solvent
Prior art date
Application number
PCT/GB2003/002117
Other languages
English (en)
Other versions
WO2004011561A8 (fr
Inventor
Gavin Wright
Original Assignee
Avecia Limited
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 GB0217446A external-priority patent/GB0217446D0/en
Application filed by Avecia Limited filed Critical Avecia Limited
Priority to AU2003227942A priority Critical patent/AU2003227942A1/en
Priority to EP03725407A priority patent/EP1532216A1/fr
Priority to JP2004523900A priority patent/JP2005533899A/ja
Priority to US10/522,368 priority patent/US20050211131A1/en
Priority to MXPA05000932A priority patent/MXPA05000932A/es
Publication of WO2004011561A1 publication Critical patent/WO2004011561A1/fr
Publication of WO2004011561A8 publication Critical patent/WO2004011561A8/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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/34—Preparation from o-monohydroxy azo compounds having in the o'-position an atom or functional group other than hydroxyl, alkoxy, carboxyl, amino or keto groups

Definitions

  • UP ink jet printing
  • inks used in UP there are many demanding performance requirements for inks used in UP. For example they desirably provide sharp, non-feathered images having good water-fastness, light-fastness and optical density.
  • 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.
  • WO 01/48090 relates to metal chelate azo compounds which comprise a naphthol component and certain heterocyclic groups. WO 01/48090 does not disclose such compounds further substituted by a triazole ring for use in ink formulations.
  • an ink comprising:
  • the inks comprising the compound of Formula (1) are magenta in colour.
  • the inks comprising the compound of Formula (1) provide prints which exhibit a high light-fastness, good fastness to oxidising gases such as ozone and good optical density, particularly when used for ink jet printing.
  • the inks according to the present invention are also highly soluble which improves operability and reduces crusting and nozzle blockage when inks containing the compounds are used in an ink jet printer.
  • the compound of Formula (1) is in the form of a sodium, lithium, potassium, ammonium or substituted ammonium salt, because we have found that these salts provide prints which exhibit a high light-fastness when incorporated into an ink jet printing ink.
  • the metal chelate compound of Formula (1 ) or a salt thereof according to the present invention and the inks comprising the compound of Formula (1) also include tautomers thereof, especially tautomers of the triazole ring.
  • the compound of Formula (1) may be converted into a salt using known techniques. For example, an alkali metal salt of a compound may be converted into a salt with ammonia or an amine by dissolving an alkali metal salt of the dye in water and passing the solution through a column of a suitably modified ion exchange resin.
  • the inks according to the present invention may be, and preferably are, purified to remove undesirable impurities before they are incorporated into inks for ink jet printing.
  • Conventional techniques may be employed for purification, for example ultrafiltration, reverse osmosis and/or dialysis.
  • the liquid medium preferably comprises:
  • the number of parts by weight of component (a) of the ink is preferably from 0.01 to
  • component (b) is preferably from 99.99 to 70, more preferably from 99.9 to 80, especially from 99.5 to 85, and more especially from 99 to 95 parts.
  • the number of parts of (a) + (b) is 100 and all parts mentioned herein are by weight.
  • 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 compound(s) of component (a) of the ink precipitating if evaporation of the liquid medium occurs during storage.
  • 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. It is preferred that 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 1-6 -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, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol and thiodig
  • the liquid medium comprises water and 2 or more, especially from 2 to 8, water-miscible organic solvents.
  • 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 1-4 -alkyl and C 1-4 -alkyl 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.
  • 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 metal chelate compound in the liquid medium.
  • polar solvents include C 1-4 -alcohols.
  • the liquid medium is an organic solvent free from water it comprises a ketone (especially methyl ethyl ketone) and/or an alcohol (especially a C- M -alkanol, such as 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.
  • An especially preferred ink comprises: (i) 1 to 10 parts in total of the compound of Formula (1 ) or salt thereof;
  • component (i) of the ink may comprise a compound of the Formula (1) or salt thereof, as hereinbefore defined.
  • 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.
  • a compound of Formula (1 ) may be dissolved in the low melting point solid or may be finely dispersed in it.
  • the inks according to the present invention may also contain additional components conventionally used in ink jet printing inks, for example viscosity and surface tension modifiers, corrosion inhibitors, biocides, kogation reducing additives, anti-cockle agents to reduce paper curling and surfactants which may be ionic or non-ionic.
  • the pH of the ink is preferably from 4 to 11 , more preferably from 7 to 10.
  • the viscosity of the ink at 25°C is preferably less than 50cP, more preferably less than 20 cP and especially less than 5cP.
  • a second aspect of the present invention provides a process for printing an image on a substrate comprising applying thereto by means of an ink jet printer an ink according to the first aspect of the present invention.
  • the preferences for the ink used in this process are as hereinbefore defined in relation to the first 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 papers include, HP Premium Coated Paper, HP Photopaper (all available from Hewlett Packard Inc.), Stylus Pro 720 dpi Coated Paper, Epson Photo Quality Glossy Film, Epson Photo Quality Glossy Paper (available from Seiko Epson Corp.), Canon HR 101 High Resolution Paper, Canon GP 201 Glossy Paper, Canon HG 101 High Gloss Film (all available from Canon Inc.), Wiggins Conqueror paper (available from Wiggins Teape Ltd), Xerox Acid Paper and Xerox Alkaline paper, Xerox Acid Paper (available from Xerox).
  • a third aspect of the present invention provides a substrate, preferably a paper, an overhead projector slide or a textile material, printed with an ink according to the first aspect of the present invention or by means of the process according to the second aspect of the present invention.
  • an ink jet printer cartridge comprising a chamber and ink, wherein the ink is present in the chamber and the is as defined in the first aspect of the present invention.
  • an ink jet printer containing an ink jet printer cartridge, wherein the ink jet printer cartridge is as defined in the fourth aspect of the present invention.
  • Acetic anhydride (350 ml, 3.8mol) was added dropwise to a suspension of 2- hydroxynaphthalene-3,6-disulphonic acid di sodium salt (87g, 0.25mol) in N,N- dimethylacetamide (350ml). The reaction mixture was stirred at 125°C for 24 hours, cooled to room temperature and added to acetone (2500ml). The product was filtered off, washed with acetone (3 x 100ml) and dried to give 95.2g of a cream coloured solid.
  • 3-amino-1 ,2,4-triazole-5-carboxylic acid hydrate (1.28g, 0.01 mol) was suspended in water (50ml) and dissolved by the addition of 2M NaOH to pH 8.
  • Sodium nitrite (0.76g, 0.011 mol) was added and the solution stirred until the sodium nitrite had dissolved.
  • the mixture was then added dropwise to a cooled mix of ice-water (30g) and concentrated HCI (3.0ml) at 0-5°C, the mixture was stirred for 30 minutes, at 0-5°C and then excess nitrous acid was removed by adding sulphamic acid.
  • the diazo suspension was added slowly to a solution of the product from stage (b) (5.42g, 0.01 mol) in water (100ml) at pH 7-8 (2N NaOH) cooled below 5 °C.
  • the reaction mixture was then stirred-at 0-5°C for one further hour, the product was precipitated by acidification to pH 4 with 2N HCI and collected by filtration.
  • the product was then washed with water and dried in a vacuum desiccator to give 6.4g of an orange solid.
  • a solution of nickel acetate tetrahydrate (1.38g, 0.0055mol) in water (10ml) was added dropwise to the product from stage (c) (5.0g, 0.0073mol) dissolved in water (100ml) at pH 7 (2N NaOH).
  • the reaction mixture was stirred for 2 hours at ambient temperature, dialysed using SpectraPor membrane tubing (molecular weight cut off 3500) to low conductivity ( ⁇ 100 ⁇ s).
  • the inks described in Tables I and II may be prepared wherein the Compound described in the first column is the Compound made in Example 1. 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.
  • NMP N-methyl pyrollidone
  • MIBK methylisobutyl ketone
  • BDL butane-2,3-diol
  • CET cetyl ammonium bromide
  • PHO Na 2 HPO 4
  • TBT tertiary butanol
  • TDG thiodiglycol

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 Recording Methods And Recording Media Thereof (AREA)
  • Ink Jet (AREA)

Abstract

Encre contenant: (c) un composé chélaté métallique représenté par la formule (I) ou son sel, dans laquelle M représente nickel; et (b) un milieu liquide. Ces encres sont utiles pour des imprimantes à jet d'encre.
PCT/GB2003/002117 2002-07-27 2003-05-16 Encre WO2004011561A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU2003227942A AU2003227942A1 (en) 2002-07-27 2003-05-16 Ink
EP03725407A EP1532216A1 (fr) 2002-07-27 2003-05-16 Encre
JP2004523900A JP2005533899A (ja) 2002-07-27 2003-05-16 インク
US10/522,368 US20050211131A1 (en) 2002-07-27 2003-05-16 Ink
MXPA05000932A MXPA05000932A (es) 2002-07-27 2003-05-16 Tinta.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB0217446.4 2002-07-27
GB0217446A GB0217446D0 (en) 2002-07-27 2002-07-27 Composition use and process
US41081002P 2002-09-16 2002-09-16
US60/410,810 2002-09-16

Publications (2)

Publication Number Publication Date
WO2004011561A1 true WO2004011561A1 (fr) 2004-02-05
WO2004011561A8 WO2004011561A8 (fr) 2005-02-17

Family

ID=31189606

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2003/002117 WO2004011561A1 (fr) 2002-07-27 2003-05-16 Encre

Country Status (6)

Country Link
EP (1) EP1532216A1 (fr)
JP (1) JP2005533899A (fr)
CN (1) CN1671806A (fr)
AU (1) AU2003227942A1 (fr)
MX (1) MXPA05000932A (fr)
WO (1) WO2004011561A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004078859A1 (fr) * 2003-03-06 2004-09-16 Avecia Inkjet Limited Colorants magenta a base de chelates de metaux et leur utilisation dans des imprimantes a jet d'encre
US7119178B2 (en) 2004-06-10 2006-10-10 Eastman Kodak Company Multimetallic polymeric azo colorants
US7238227B2 (en) 2003-03-06 2007-07-03 Fujifilm Imaging Colorants Limited Magenta metal chelate dyes and their use in ink-jet printers
US7449500B2 (en) 2004-06-10 2008-11-11 Eastman Kodak Company Ink jet ink containing multimetallic polymeric colorants

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1527141B1 (fr) * 2002-07-27 2010-01-27 FUJIFILM Imaging Colorants Limited Procedes, compositions et composes

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1270676A1 (fr) * 2001-06-19 2003-01-02 Mitsubishi Chemical Corporation Colorant métallifère pour enregistrement par jet d'encre, liquide aqueux pour enregistrement par jet d'encre comprenant un tel colorant et procédé d'enregistrement par jet d'encre utilisant un tel colorant

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1270676A1 (fr) * 2001-06-19 2003-01-02 Mitsubishi Chemical Corporation Colorant métallifère pour enregistrement par jet d'encre, liquide aqueux pour enregistrement par jet d'encre comprenant un tel colorant et procédé d'enregistrement par jet d'encre utilisant un tel colorant

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 76, no. 14, 3 April 1972, Columbus, Ohio, US; abstract no. 80560, YUSUPOV M. YU. ET AL: "synthesis of azo compounds based on aminotriazolecarboxylic acid and some of their analytical characteristics" XP009016502 *
CHEMICAL ABSTRACTS, vol. 97, no. 10, 6 September 1982, Columbus, Ohio, US; abstract no. 73900, HIRSCH BODO ET AL: "some new dyes based on 3-amino-1,2,4-triazole derivatives" XP009016260 *
DOKLADY AKADEMII NAUK TADZHIKSKOI SSR, vol. 14, no. 9, 1971, pages 31 - 3 *
SBORNIK VEDECKYCH PRACI-VYSOKA SKOLA CHEMICKOTECHNOLOGICKA PARDUBICE, vol. 44, 1981, pages 285 - 90 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004078859A1 (fr) * 2003-03-06 2004-09-16 Avecia Inkjet Limited Colorants magenta a base de chelates de metaux et leur utilisation dans des imprimantes a jet d'encre
US7238227B2 (en) 2003-03-06 2007-07-03 Fujifilm Imaging Colorants Limited Magenta metal chelate dyes and their use in ink-jet printers
US7119178B2 (en) 2004-06-10 2006-10-10 Eastman Kodak Company Multimetallic polymeric azo colorants
US7449500B2 (en) 2004-06-10 2008-11-11 Eastman Kodak Company Ink jet ink containing multimetallic polymeric colorants

Also Published As

Publication number Publication date
AU2003227942A1 (en) 2004-02-16
MXPA05000932A (es) 2005-07-22
WO2004011561A8 (fr) 2005-02-17
CN1671806A (zh) 2005-09-21
JP2005533899A (ja) 2005-11-10
EP1532216A1 (fr) 2005-05-25

Similar Documents

Publication Publication Date Title
EP1056808B1 (fr) Colorants monoazo, composition et encre d'impression a jet d'encre contenant lesdits colorants
US7163576B2 (en) Disazo dyes and ink jet inks containing them
US20050274280A1 (en) Metal chelate compounds and inks
WO2003095563A1 (fr) Colorants tris-azo pour impression a jet d'encre
US7156908B2 (en) Phthalocyanine compounds, ink compositions comprising said compounds, and printing process therewith
US6652637B1 (en) Disazo dyes and inks containing them
WO1998044053A1 (fr) Composition d'encre contenant deux colorants azoiques
US7270406B2 (en) Ink
WO2004011560A2 (fr) Procedes, compositions et composes
US6712893B1 (en) Dis-azo dyestuffs and use thereof in ink-jet printing
WO2004011561A1 (fr) Encre
US6559292B1 (en) Disazo dyes and inks containing them
US6746525B1 (en) Disazo dyes and inks containing them
EP1228148B1 (fr) Colorants disazo pour impression a jet d'encre
US20050211131A1 (en) Ink
WO2007045829A2 (fr) Colorants azoiques jaunes pour impression a jet d'encre
US7481523B2 (en) Monoazo compounds and inks containing them
US6689201B1 (en) Disazo dyes and inks containing them
KR20050023352A (ko) 잉크
WO1999013008A1 (fr) Colorants disazoiques solubles dans l'eau et encres pour procede d'impression par jets d'encre contenant ces colorants

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NI NO NZ OM PH PL PT RO RU SC SD SE SG SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
CFP Corrected version of a pamphlet front page
CR1 Correction of entry in section i

Free format text: IN PCT GAZETTE 06/2004 UNDER (71) REPLACE "AVENCIA LIMITED" BY "AVECIA LIMITED"

WWE Wipo information: entry into national phase

Ref document number: 3992/DELNP/2004

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 1020047021542

Country of ref document: KR

WWE Wipo information: entry into national phase

Ref document number: 2003725407

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2004523900

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: PA/a/2005/000932

Country of ref document: MX

WWE Wipo information: entry into national phase

Ref document number: 10522368

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 20038179180

Country of ref document: CN

CFP Corrected version of a pamphlet front page
CR1 Correction of entry in section i

Free format text: IN PCT GAZETTE 06/2004 UNDER (71) REPLACE "APPLICANT (FOR US ONLY)" BY "APPLICANT (FOR ALL DESIGNATED STATES EXCEPT US)"

WWP Wipo information: published in national office

Ref document number: 1020047021542

Country of ref document: KR

WWP Wipo information: published in national office

Ref document number: 2003725407

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 2003725407

Country of ref document: EP