WO2001066648A1 - Compose, compositions et utilisation - Google Patents

Compose, compositions et utilisation Download PDF

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Publication number
WO2001066648A1
WO2001066648A1 PCT/GB2001/000570 GB0100570W WO0166648A1 WO 2001066648 A1 WO2001066648 A1 WO 2001066648A1 GB 0100570 W GB0100570 W GB 0100570W WO 0166648 A1 WO0166648 A1 WO 0166648A1
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WO
WIPO (PCT)
Prior art keywords
formula
compound according
phthalocyanine
optionally substituted
independently
Prior art date
Application number
PCT/GB2001/000570
Other languages
English (en)
Inventor
Prakash Patel
Paul Wight
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
Application filed by Avecia Limited filed Critical Avecia Limited
Priority to AU2001232080A priority Critical patent/AU2001232080A1/en
Publication of WO2001066648A1 publication Critical patent/WO2001066648A1/fr

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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
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
    • C09B47/26—Amide radicals
    • 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
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • 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

Definitions

  • This invention relates to dyes, to compositions containing these dyes, to inks, to printing processes, to printed substrates and to ink jet printer cartridges.
  • 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.
  • Dyes containing a single copper phthalocyanine group and their use in ink jet printing are known.
  • Cl Direct Blue 199 and Cl Direct Blue 86 are used as colorants in commercial ink jet printing inks.
  • each Pc independently is an optionally substituted phthalocyanine group; and L is a divalent linking group; provided that:
  • L is free from halo-s-triazine groups; and (ii) L is not -NH-CH 2 -CH 2 -NH-CH 2 -CH 2 -NH-.
  • L is a group of Formula (2):
  • R 1 is H, optionally substituted alkyl or optionally substituted aryl
  • L 1 is a divalent linking group
  • L is free from halo-s-triazine groups; and (ii) L is not -NH-CH 2 -CH 2 -NH-CH 2 -CH 2 -NH-.
  • L comprises one or more carbon atoms and optionally one or more heteroatoms, preferably nitrogen, oxygen and/or sulphur. More preferably L 1 comprises from 1 to 30, especially 2 to 20 carbon atoms and 0 to 20 atoms, especially 1 to 10 atoms selected from oxygen nitrogen and sulphur.
  • L 1 is of Formula (3):
  • each G independently is optionally substituted alkylene or arylene; each X independently is an ester, amide, amine, sulphone, sulphoxide, ether or thioether; n is from 1 to 6; and p has a value of from 0 to 10; provided that:
  • L is free from halo-s-triazine groups; and (ii) L is not -NH-CH 2 -CH 2 -NH-CH 2 -CH 2 -NH-.
  • each G independently is optionally substituted C 1-6 alkylene or optionally substituted phenylene.
  • each X independently is a group of formula -CO 2 -, -CONR 2 -, -NR 2 -, -O-, -SO-, -SO 2 - or -S- wherein R 2 is H or optionally substituted C 1-4 alkyl.
  • n is 2, 3 or 4, more preferably 2 or 3 especially 2.
  • the value of n may vary from one group of formula (C n H 2n - X) to another, but preferably n has the same value in all groups of formula (C n H 2n - X).
  • p has a value of from 0 to 8, more preferably 0 to 6, especially 0,1 ,2,3,4 or 5.
  • one G is optionally substituted phenylene and the other G is optionally substituted phenylene or optionally substituted C 1-6 alkylene and each X independently is -O-, -SO-, -SO 2 - or -NR 2 - wherein R 2 is H or optionally substituted C ⁇ alkyl, n is 2 or 3 and p is 0, 1 , 2, 3, 4 or 5.
  • the optional substituents which may be present on G are preferably selected from
  • R 3 and R 4 are each independently H or optionally substituted C 1-4 alkyl or, in the case of -CO 2 R 3 and -SO 2 R 3 ,
  • R 3 may also be a cation (especially a metal or optionally substituted ammonium cation).
  • Preferred phthalocyanine groups represented by Pc are each independently selected from metal-free phthalocyanines and metal-containing phthalocyanines. More preferably phthalocyanine groups represented by Pc are each independently selected from copper phthalocyanine and nickel phthalocyanine.
  • At least one, and preferably both, of the phthalocyanine groups carries a sulpho substituent. It is also preferred that at least one, and preferably both, of the phthalocyanine groups carries a sulphonamide substituent, preferably of the formula SO 2 NR 5 R 6 wherein R 5 and R 6 are each independently H, optionally substituted alkyl, optionally substituted aryl or R 5 and R 6 together with the N atom to which they are attached form an optionally substituted five or six membered ring.
  • R 5 and R 6 are each independently H or optionally substituted C ⁇ -alkyi, especially H or methyl. It is especially preferred that at least one of the phthalocyanine groups carries a sulpho substituent and a sulphonamide substituent of the formula SO 2 NR 5 R 6 wherein R 5 and R 6 are as hereinbefore defined.
  • R 5 and R 6 are preferably each independently selected from sulpho, carboxy, phosphato, hydroxy and amino.
  • the compounds described herein are water-soluble.
  • Compounds of the type as herein described may be prepared by a process comprising condensing at least two molar equivalents of a phthalocyanine compound carrying a group of formula -SO 2 Z, wherein Z is a labile group, with a divalent linking group reactive towards -SO 2 Z groups.
  • the compounds may be prepared by condensing a phthalocyanine compound carrying a substituent of the formula -SO 2 NR 1 -L 1 -NH 1 H with a phthalocyanine compound carrying a substituent of the formula -SO 2 Z, wherein Z is a labile group and L 1 and R 1 independently are as defined above.
  • Typical labile groups are halogens, especially chloro.
  • 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) 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 liquid dye 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
  • the liquid medium comprises water and 2 or more, especially from 2 to 8, water-soluble 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 t ethyleneglycol; and mono- C ⁇ -alkyl and C 1-4 -alkyl ethers of diols, more preferably mono-C ⁇ -alkyl ethers of diols having 2 to 12 carbon atoms, especially 2-methoxy-2-ethoxy-2-ethoxyethanol.
  • colorants may be present in the liquid medium to modify the shade and performance properties of the composition.
  • colorants include C.I. Direct Yellow 86, 132, 142 and 173; C.I. Direct Blue 199, and 307; C.I. Food Black 2; C.I. Direct Black 168 and 195; C.I. Acid Yellow 23; and any of the dyes used in ink jet printers sold by Seiko Epson Corporation, Hewlett Packard Company, Canon Inc. & Lexmark International. Addition of such further dyes can increase overall solubility leading to less kogation (nozzle blockage) for the resultant ink.
  • liquid media comprising a mixture of water and one or more organic solvents
  • the liquid medium comprises an organic solvent free from water, (i.e. less than 1 % water by weight)
  • 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.
  • a polar solvent is included because this enhances solubility of the dye in the liquid medium.
  • Examples of polar solvents include C ⁇ -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 1-4 -alkanol, more especially ethanol or propanol).
  • a ketone especially methyl ethyl ketone
  • 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 organic solvent free from water it is a mixture of 2 to 5 different organic solvents. This allows a medium to be selected which gives good control over the drying characteristics and storage stability of the ink.
  • Liquid 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.
  • the composition has been filtered through a filter having a mean pore size below 10 ⁇ m, more preferably below 3 ⁇ m, especially below 2 ⁇ m, more especially below 1 ⁇ m.
  • This filtration removes particulate matter which could otherwise block the fine nozzles found in many ink jet printers.
  • compositions preferably have a total concentration of divalent and trivalent metal ions other than those associated with the phthalocyanine below 1000, more preferably below 100, especially below 20, more especially below 10 parts per million by weight relative to the total weight of ink.
  • Pure compositions of this type may be prepared by using high purity ingredients and/or by purifying the composition after it has been prepared. Suitable purification techniques are well known, e.g. ultrafiltration, reverse osmosis, ion exchange and combinations thereof.
  • the liquid medium may also contain further components which are 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.
  • the composition may be an ink, especially an ink-jet printing ink, or a liquid dye concentrate which is used to prepare inks.
  • the concentrates are useful as a means for transporting colorant and so minimising costs associated with drying the dye and transporting excess liquid.
  • the compounds of Formula (1 ) have attractive, strong cyan shades and are valuable colorants for ink-jet printing inks. They benefit from a good balance of solubility, storage stability and fastness to water and light.
  • the compounds of Formula (1) are stable to oxidative gases such as ozone, nitrous oxide, NO and NO 2 .
  • the compounds of Formula (1 ) particularly benefit from their stability to ozone.
  • a third aspect of the invention provides a process for printing an image on a substrate comprising applying a composition according to the second aspect of the current invention to the substrate by means of an ink jet printer.
  • the ink jet printer preferably applies the composition 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 composition in a reservoir by means of a resistor adjacent to the orifice, thereby causing the composition 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 composition 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.
  • a fourth aspect of the present invention provides a substrate, especially paper, an overhead projector slide, a textile material, a plastic, glass and metal, printed with a composition, a compound or by means of a process as hereinbefore defined.
  • a fifth aspect of the present invention provides an ink jet printer cartridge comprising a chamber and a composition wherein the composition is in the chamber and the composition is as described according to the second aspect of the present invention.
  • a sixth aspect of the invention is a method for the coloration of a substrate which comprises applying thereto a compound according to the first aspect of the invention.
  • Step 1 Preparation of:
  • step 1 The product of step 1 (10.6g) was stirred in water (600ml) at room temperature and pH 9-10.
  • Cl Reactive Blue 25 (11.3g) was added stepwise and the pH maintained at 9-10 using 2M NaOH.
  • Sulphuric acid (9.4g) was added to chlorosulphonic acid (192g) followed by copper phthalocyanine (38.4g) below 60°C.
  • the reaction mixture was heated at 130-140°C for 2hr, cooled and drowned out into ice/water (480g).
  • the precipitated solid was filtered-off and washed with 0.5M HCI (600ml).
  • the solid was added stepwise to a stirred solution of ethylene diamine (4g) in ice/water (340g).
  • the reaction mixture was then heated at 40°C, pH7-8 for 2hr, cooled and the pH was lowered to 3-4 using concentrated HCI.
  • the precipitate was filtered-off and washed with saturated brine to give the compound shown above.
  • step 2 The product of step 2 was added to a mixture of p-aminobenzenesulphatoethyl sulphone (133g) in water (700 ml) at pH 5.2 (adjusted by adding 15 % aqueous NaOH). The mixture was stirred at pH 5.2 and room temperature for 3 hours. Sodium chloride (20% w/v) was added to the mixture which was stirred for 15 minutes and the pH of the mixture was adjusted to 1.0 with concentrated hydrochloric acid. The resultant precipitate was collected by filtration at reduced pressure and washed with ice-cold brine (10%) and dried under reduced pressure to obtain 688 g of product.
  • Step 4 The product of step 1 (23g) was added portion-wise to a stirred solution of the product of step 3 (148 g, 28% strength) in water (1000ml) at pH 9-10 and room temperature. The mixture was heated at 70°C for 4.5 hr at pH 9-10 and then cooled and the pH lowered to pH 3-4 using concentrated HCI. The precipitated solid was filtered-off, washed with 0.5M HCI, converted to the sodium salt, desalinated and dried to give the product (62g) having absorbance maxima at 625 and 665 nm. Analysis by mass spectroscopy revealed multiple species of which the title product was the major component.
  • Example 1 The product of Example 1 , Step 1 (20g) was added to a solution of the product of Example 2 Step 3 (92g, 28% strength) in water (1000ml) at pH 9-10. The mixture was heated at 70°C for 4hr, cooled and the pH lowered to 3-4 with concentrated HCI. The precipitate was filtered-off, washed with 0.5M HCI, converted to the sodium salt, desalinated and dried to give the product as a solid (30g) having absorbance maxima at 625 and 660 nm. Analysis by mass spectroscopy revealed multiple species of which the title product was the major component.
  • Step 1
  • Copper phthalocyanine (115.2g) was added to chlorosulphonic acid (308ml) below 50°C and then heated at 140°C for 3hr. The mixture was cooled to 40°C and phosphorous trichloride (52g) was added over 1 hr below 50°C. The mixture was then heated at 90°C for 1.5 hr, cooled and poured into ice/water (1400ml). The solid was filtered-off and washed with 0.5M HCI (2000ml).
  • Step 1 (18g) was added to the product of Example 2, Step 3 (130g, 28% strength) in aqueous (2000ml) pH 9-10 solution.
  • the reaction mixture was heated at
  • Step 2 The compound shown in Example 2, Step 2 (90g, 28% strength) was dissolved in water (1000ml). 4,7,10-trioxatridecadiamine (2.2g) was added and the pH was maintained at 9-10 by the addition of 2M NaOH. The reaction mixture was stirred at room temperature for 1 hr and then at 70°C for 2.5 hr, cooled and pH lowered to 2-3 with concentrated HCI. The precipitate was filtered-off, converted to the sodium salt, desalinated and dried to give the product (23g) as a solid having absorbance maxima at 630 and 665 nm. Analysis by mass spectroscopy revealed multiple species of which the title product was the major component.
  • Inks were prepared by dissolving 3 parts (weight by weight) of the dye in a stock solution of 5 parts 2-pyrrolidone, 5 parts thiodiglycol, 2 parts Surfynol 465 (a surfactant commercially available from Air Products Inc.) and 85 parts distilled water with the addition of concentrated sodium hydroxide to give a pH of 8.5 to 9.
  • the resultant inks were as follows:
  • the Comparative Dye was C.I. Direct Blue 199, a copper phthalocyanine dye obtained from Avecia Limited.
  • Each ink was filtered through a 0.45 ⁇ m filter and put into one chamber of a Canon trichamber inkjet cartridge.
  • Inks 1 and 2 were then ink jet printed onto each of the substrates shown in Tables A to F using a Canon 4300 U printer, the following results were obtained:
  • the CIE colour co-ordinates of each print (a, b, L, Chroma) were measured using a Xrite 983 Spectrodensitometer with 0°/45° measuring geometry with a spectral range of 400-700nm at 20nm spectral intervals, using illuminant C with a 2° (CIE 1931 ) observer angle and a density operation of status T. No less than 4 measurements were taken diagonally across a solid colour block on the print with a size greater than 10mm x 10mm.
  • the OD is the optical density of the printed paper, as measured by a Xrite 983 Spectrodensitometer Table A: Ink 1
  • 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.
  • TDG thiodiglycol

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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)
  • General Chemical & Material Sciences (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)

Abstract

L'invention concerne un composé de la formule (1): Pc-SO2-L-SO2-Pc dans laquelle chaque Pc représente indépendamment un groupe phtalocyanine facultativement substitué; et L représente un groupe de liaison divalent; à condition que: (i) L soit exempt de groupes halo-s-triazine; et (ii) L ne représente pas -NH-CH2-CH2-NH-CH2-CH2-NH-. L'invention concerne également des encres contenant ces composés, des cartouches d'imprimante à jet d'encre contenant ces encres, leur utilisation dans l'impression par jet d'encre et des substrats imprimés avec ces composés et/ou encres.
PCT/GB2001/000570 2000-03-07 2001-02-12 Compose, compositions et utilisation WO2001066648A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001232080A AU2001232080A1 (en) 2000-03-07 2001-02-12 Compound, compositions and use

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0005299A GB0005299D0 (en) 2000-03-07 2000-03-07 Compound, compositions and use
GB0005299.3 2000-03-07

Publications (1)

Publication Number Publication Date
WO2001066648A1 true WO2001066648A1 (fr) 2001-09-13

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003062323A1 (fr) * 2002-01-22 2003-07-31 Fuji Photo Film Co., Ltd. Encre contenant un compose de phtalocyanine soluble dans l'eau pour impression a jet d'encre, procede d'impression a jet d'encre et procede reduisant la decoloration due a l'ozone dans une image coloree
EP1350819A1 (fr) * 2002-04-03 2003-10-08 Fuji Photo Film Co., Ltd. Une encre et une méthode d'enregistrement par jet d'encre
EP1473335A1 (fr) * 2002-02-08 2004-11-03 Fuji Photo Film Co., Ltd. Encre d'impression a jet d'encre et procede d'impression a jet d'encre
WO2005014725A1 (fr) * 2003-07-18 2005-02-17 Avecia Inkjet Limited Phthalocyanines et leur utilisation dans les imprimantes a jet d'encre
WO2005014724A1 (fr) * 2003-07-18 2005-02-17 Avecia Inkjet Limited Phthalocyanines et leur utilisation des les imprimantes a jet d'encre

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325511A (en) * 1964-06-08 1967-06-13 Martin Marietta Corp Phthalocyanine dyestuffs
US3674783A (en) * 1969-06-16 1972-07-04 Sandoz Ltd Phthalocyanine compounds
FR2643379A1 (fr) * 1989-02-23 1990-08-24 Sandoz Sa Nouvelles phtalocyanines, leur preparation et leur utilisation comme colorants
EP0418792A1 (fr) * 1989-09-19 1991-03-27 Canon Kabushiki Kaisha Encre, méthode d'enregistrement par jet d'encre utilisant cette encre, méthode pour produire cette encre et utilisation de cette encre pour enregistrement sur un substrat
EP0471456A1 (fr) * 1990-08-15 1992-02-19 Zeneca Limited Colorants
WO1997013812A1 (fr) * 1995-10-07 1997-04-17 Zeneca Limited Composes de phthalocyanine
EP0906943A1 (fr) * 1996-05-30 1999-04-07 Nippon Kayaku Co., Ltd. Fluides d'impression contenant des composes cuivre-phtalocyanine

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325511A (en) * 1964-06-08 1967-06-13 Martin Marietta Corp Phthalocyanine dyestuffs
US3674783A (en) * 1969-06-16 1972-07-04 Sandoz Ltd Phthalocyanine compounds
FR2643379A1 (fr) * 1989-02-23 1990-08-24 Sandoz Sa Nouvelles phtalocyanines, leur preparation et leur utilisation comme colorants
EP0418792A1 (fr) * 1989-09-19 1991-03-27 Canon Kabushiki Kaisha Encre, méthode d'enregistrement par jet d'encre utilisant cette encre, méthode pour produire cette encre et utilisation de cette encre pour enregistrement sur un substrat
EP0471456A1 (fr) * 1990-08-15 1992-02-19 Zeneca Limited Colorants
WO1997013812A1 (fr) * 1995-10-07 1997-04-17 Zeneca Limited Composes de phthalocyanine
EP0906943A1 (fr) * 1996-05-30 1999-04-07 Nippon Kayaku Co., Ltd. Fluides d'impression contenant des composes cuivre-phtalocyanine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 69, no. 16, 14 October 1968, Columbus, Ohio, US; abstract no. 60042z, XP002166210 *

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100845446B1 (ko) * 2002-01-22 2008-07-10 후지필름 가부시키가이샤 잉크 분사법용 수용성 프탈로시아닌 화합물 함유 잉크,잉크 분사식 기록 방법 및 채색 화상 재료의 오존 가스변색의 개선 방법
US7219988B2 (en) 2002-01-22 2007-05-22 Fuji Photo Film Co., Ltd. Water-soluble phthalocyanine compound-containing ink for ink jetting, ink jet recording method and method for improving ozone gas discoloration of colored image material
WO2003062323A1 (fr) * 2002-01-22 2003-07-31 Fuji Photo Film Co., Ltd. Encre contenant un compose de phtalocyanine soluble dans l'eau pour impression a jet d'encre, procede d'impression a jet d'encre et procede reduisant la decoloration due a l'ozone dans une image coloree
EP1473335A1 (fr) * 2002-02-08 2004-11-03 Fuji Photo Film Co., Ltd. Encre d'impression a jet d'encre et procede d'impression a jet d'encre
US7311392B2 (en) 2002-02-08 2007-12-25 Fujifilm Corporation Inkjet recording ink and method of inkjet recording
EP1473335A4 (fr) * 2002-02-08 2005-04-13 Fuji Photo Film Co Ltd Encre d'impression a jet d'encre et procede d'impression a jet d'encre
CN100346968C (zh) * 2002-02-08 2007-11-07 富士胶片株式会社 喷墨记录用墨水和喷墨记录方法
US7208034B2 (en) 2002-04-03 2007-04-24 Fujifilm Corporation Inkjet recording ink and inkjet recording method
EP1350819A1 (fr) * 2002-04-03 2003-10-08 Fuji Photo Film Co., Ltd. Une encre et une méthode d'enregistrement par jet d'encre
US7182806B2 (en) 2003-07-18 2007-02-27 Fujifilm Imaging Colorants Limited Phthalocyanines and their use in ink-jet printers
JP2006528710A (ja) * 2003-07-18 2006-12-21 フジフィルム・イメイジング・カラランツ・リミテッド フタロシアニン類およびインキジェットプリンターにおけるそれらフタロシアニンの使用
GB2417249A (en) * 2003-07-18 2006-02-22 Avecia Inkjet Ltd Phthalocyanines and their use in ink-jet printers
GB2417249B (en) * 2003-07-18 2007-11-21 Avecia Inkjet Ltd Phthalocyanines and their use in ink-jet printers
WO2005014724A1 (fr) * 2003-07-18 2005-02-17 Avecia Inkjet Limited Phthalocyanines et leur utilisation des les imprimantes a jet d'encre
WO2005014725A1 (fr) * 2003-07-18 2005-02-17 Avecia Inkjet Limited Phthalocyanines et leur utilisation dans les imprimantes a jet d'encre
US7678899B2 (en) 2003-07-18 2010-03-16 Fujifilm Imaging Colorants Limited Phthalocyanines and their use in ink-jet printers

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