WO2002034844A1 - Composition contenant une azaphthalocyanine et utilisation - Google Patents

Composition contenant une azaphthalocyanine et utilisation Download PDF

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Publication number
WO2002034844A1
WO2002034844A1 PCT/GB2001/004374 GB0104374W WO0234844A1 WO 2002034844 A1 WO2002034844 A1 WO 2002034844A1 GB 0104374 W GB0104374 W GB 0104374W WO 0234844 A1 WO0234844 A1 WO 0234844A1
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WIPO (PCT)
Prior art keywords
carboxy
composition
independently
sulpho
group
Prior art date
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PCT/GB2001/004374
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English (en)
Inventor
Peter Gregory
Clive Edwin Foster
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Avecia Limited
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Application filed by Avecia Limited filed Critical Avecia Limited
Priority to AU2001292047A priority Critical patent/AU2001292047A1/en
Publication of WO2002034844A1 publication Critical patent/WO2002034844A1/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
    • 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
    • C09B47/00—Porphines; Azaporphines
    • 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
    • C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/065—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide having -COOH or -SO3H radicals or derivatives thereof, directly linked to the skeleton

Definitions

  • This invention relates to compounds, to compositions containing these compounds, to inks, to printing processes, to printed substrates and to ink-jet printer cartridges.
  • Ink-jet printing 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.
  • Water-fastness is a particular problem with aqueous ink-jet printing inks.
  • the dye should be as soluble as possible to minimise the risk of blockage of the ink-jet nozzle.
  • high solubility in water is responsible for poor water fastness on paper. Prints formed using dyes with poor water- fastness readily smudge when handled with moist fingers or if tea, coffee or water is accidentally spilled on them.
  • Dyes containing a single copper phthalocyanine group and their use in ink-jet printing are known.
  • C.I. Direct Blue 199 and C.I. Direct Blue 86 are copper phthalocyanine dyes used as colorants in commercial ink-jet printing inks.
  • Certain azaphthalocyanine compounds are known from Canadian Patent 2133284 to be useful for photodyamic therapy of cancer and treatment of blood products. Japanese
  • Patent publications JP2129650 and JP4124188 describe the use of certain insoluble azaphthalocyanines in electrophotography.
  • European patent publication EP965874 describes the use of various azaphthalocyanines in the manufacture of colour filters.
  • a process for coloration of paper comprising applying thereto a composition comprising a medium and an. azaphthalocyanine compound.
  • a composition comprising a medium and an. azaphthalocyanine compound.
  • the composition is applied to the paper by means of a printing process, more preferably by means of an ink-jet printer.
  • the ink-jet printer preferably applies the composition to the paper 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 paper 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 ink can be ejected by an electromechanical actuator connected to a moveable paddle or plunger as for example described in International Patent Applications WO 00/48938 and WO 00/55089.
  • Preferred papers are plain, treated or coated papers which may have an acid, alkaline or neutral character.
  • the azaphthalocyanine compound is preferably water-soluble, more preferably it has from 1 to 8 water-solubilising groups.
  • Preferred azaphthalocyanine compounds are of Formula (1):
  • each A independently is CH or N;
  • M is 2H, Si, a metal, an oxymetal group, a hydroxymetal group or a halometal group; each D independently is an acidic water solubilising group; each E independently is an optional substituent; m is 0 to 8; and n is 0 to 8.
  • all groups represented by A are CH or all groups represented by A are N.
  • M is preferably 2Li, 2Na, 2K, Mg, Ca, Ba, Al, Si, Sn, Pb, Rh, Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, AIX, GaX, InX or SiX 2 , where in X is OH or Cl, more preferably Sc, Ti, Va, Cr, Mn, Fe, Co, Zn, Ni and Cu especially Cu or Ni.
  • each D independently is carboxy, phosphate), sulpho or hydrocarbyl carrying at least one group selected from carboxy, phosphato and sulpho. It is especially preferred that each D independently is carboxy or hydrocarbyl carrying at least one group selected from carboxy, sulpho and phosphato (particularly carboxy and sulpho).
  • Hydrocarbyl groups include alkyl, alkenyl, alkynyl and aryl groups and any combination thereof (such as aralkyl and alkaryl) optionally interrupted by one or more bivalent radicals such as -CO 2 -, -CONR 1 -, -NR 1 -, -O-, -SO-, -SO 2 - or -S- wherein R 1 is H or optionally substituted C M alkyl. More preferably each D independently is carboxy, alkyl carrying at least one group selected from carboxy and sulpho or aryl carrying at least one group selected from carboxy and sulpho.
  • each D is carboxy or each D is aryl (especially phenyl) carrying at least one sulpho group.
  • each E independently is H, optionally substituted alkyl (preferably C 1 - alkyl), optionally substituted alkoxy (preferably C M -alkoxy), optionally substituted aryl (preferably phenyl), optionally substituted aryloxy (preferably phenoxy), optionally substituted polyalkylene oxide (preferably polyethylene oxide or polypropylene oxide), nitro, cyano, halo, ureido, SO 2 F, hydroxy, ester, -NR 2 R 3 , -COR 2 , -CONR 2 R 3 , -NHCOR 2 , carboxyester, sulphone, and -SO 2 NR 2 R 3 , wherein R 2 and R 3 are each independently H or optionally substituted alkyl (especially C ⁇ -alkyl).
  • m is 0 to 7, more preferably 0 to 4.
  • n is 1 to 8, more preferably 4 to 8, especially 4.
  • D is a hydrocarbyl group carrying at least one group selected from carboxy, phosphato and sulpho it optionally carries further substituents.
  • substituents and also the optional substituents which may be present on E are each independently selected from alkyl (preferably C ⁇ -alkyl), alkoxy (preferably C ⁇ -alkoxy), aryl (preferably phenyl), aryloxy (preferably phenoxy), polyalkylene oxide (preferably polyethylene oxide or polypropylene oxide), nitro, cyano, halo, ureido, SO 2 F, hydroxy, ester, -NR 4 R 5 , -COR 4 , -CONR 4 R 5 , - NHCOR 4 , carboxyester, sulphone and -SO 2 NR 4 R 5 , wherein R 4 and R 5 are each independently H or alkyl (especially C ⁇ -alkyl).
  • the further substituents which may be present on D and the optional substituents which may be present on E are each independently selected from methyl, ethyl, propyl, butyl, phenyl, methoxy, ethoxy, butoxy, nitro, phenoxy, cyano, carboxyester, sulphone, sulphonamide, ureido, - SO 2 NR 4 R 5 and NHCOR 4 , wherein R 4 and R 5 are as hereinbefore defined.
  • the azaphthalocyanine compound is of Formula (1) wherein A is CH or N; M is Cu or Ni; each D is carboxy or each D is aryl (especially phenyl) carrying at least one sulpho group and optionally one or more further substituents; each E independently is an optional substituent; m is 0 to 4; and n is 4 to 8.
  • D is preferably aryl (especially phenyl) carrying a sulphonic acid group and optionally one or more further substituents.
  • Any acid or basic groups on the azaphtholocyanine compound, particularly acid groups, are preferably in the form of a salt.
  • the Formulae shown herein include the compounds in free acid and in salt form.
  • Preferred salts are alkali metal salts, especially lithium, sodium and potassium, ammonium and substituted ammonium salts (including quaternary amines such as ((CH 3 ) 4 N + ) and mixtures thereof.
  • ammonium and substituted ammonium salts including quaternary amines such as ((CH 3 ) 4 N + ) and mixtures thereof.
  • salts with sodium, lithium, ammonia and volatile amines more especially sodium salts.
  • the compounds may be converted into a salt using known techniques.
  • the azaphthalocyanine compound used in the process is able to form a zwitterion or is in zwitterionic form.
  • Zwitterions bear both positive and negative charges and are overall neutral. Thus, they tend to have much lower aqueous solubility than the parent cation or anion. It is believed that the excellent solubility and water-fastness of certain of the azaphthalocyanines is due to them having an overall negative charge in an alkaline composition, thus enhancing solubility.
  • nitrogen atoms in the azaphthalocyanine ring system may become protonated, resulting in its solubility decreasing and water-fastness increasing.
  • composition used in the process is more acidic than the paper.
  • the composition has a pH >7, preferably >7.5, more preferably >8 and in each case the paper has a lower pH than the composition. While in another embodiment of the present invention the composition has a pH ⁇ 7, preferably ⁇ 6.5, more preferably ⁇ 6 and in each case the paper has a higher pH than the composition.
  • the process may be fine tuned to give optimum performance by careful selection of the nature and number of acid and basic groups present on the azaphthalocyanine, the pH of the composition and the pH of the paper.
  • azaphthalocyanine compounds having multiple anionic and cationic groups a true zwitterion may not be formed on application to the substrate. However, as the pH approaches the molecules isoelectric point a significant decrease in solubility may still be seen.
  • composition to be applied by the process comprises:
  • the medium is a liquid medium.
  • the number of parts of component (a) is preferably from 0.1 to 20, more preferably from 0.5 to 15, 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.
  • the composition may of course contain further ingredients in addition to (a) and (b).
  • 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 concentrates which may be used to prepare more dilute inks and also reduces the chance of component (a) precipitating if evaporation of the liquid medium occurs during storage.
  • Preferred liquid media include water, a mixture of water and organic solvent and 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 pentane- nb ,5- diol, ethyleneglycol, thiodiglycol, diethyleneglycol and triethyleneglycol; and mono- C ⁇ -alkyl and C ⁇ -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 included in the composition 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 colorants can increase overall solubility leading to less kogation (nozzle blockage) for the resultant composition.
  • liquid media comprising a mixture of water and one or more organic solvents are described in US 4,963,189, US 4,703,113, US 4,626,284 and EP 4,251 ,50A.
  • 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 ⁇ -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, 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.
  • 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.
  • the composition preferably has a total concentration of divalent and trivalent metal ions (other than those bound to the nitrogen atoms at the azaphthalocyanine nucleus) of below 1000, more preferably below 100, especially below 20, more especially below 10 parts per million by weight relative to the total weight of the composition.
  • 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 of course contain further additives 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.
  • a composition comprising a medium and a compound of Formula (1) as hereinbefore defined, with the proviso that n is 1 to 8 and each D independently is carboxy or hydrocarbyl carrying at least one group selected from carboxy, sulpho, and phosphato (preferably from carboxy and sulpho).
  • the medium is as hereinbefore described in the first aspect of the invention.
  • the composition is preferably 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 drying the dye and transporting excess liquid.
  • Each D independently is preferably carboxy, alkyl carrying at least one group selected from carboxy and sulpho or aryl (especially phenyl) carrying at least one group selected from carboxy and sulpho.
  • the further substituents which D may also carry are as hereinbefore described in relation to the first aspect of the present invention. It is also preferred that all groups represented by D are identical to each other, e.g. all groups represented by D are carboxy or all groups represented by D are aryl carrying at least one sulpho group.
  • the compound of Formula (1) is able to form a zwitterion or is in zwitterion form.
  • the preferences for M, m, A and E and salt forms are as hereinbefore described in the first aspect of the invention.
  • n is preferably 4 to 8.
  • the preferred ratio of compound of liquid medium and the preferred liquid media for the composition are as hereinbefore described in relation to the composition used in the process of the present invention.
  • each A is CH or N; M is Cu or Ni; each D is carboxy or each D is aryl (especially phenyl) carrying at least one sulpho group; each E is independently an optional substituent; m is 0 to 4; n is 4 to 8.
  • D is preferably optionally substituted aryl sulphonic acid.
  • a third aspect of the invention provides a compound of Formula (1) as hereinbefore defined in the first aspect of the invention, with the provisos that: (i) n is 1 to 8 and each D independently is carboxy or hydrocarbyl carrying at least one group selected from carboxy, sulpho and phosphato, and (ii) when all groups represented by A are N and D is carboxy, n is 1 to 7.
  • each D in the third aspect of the invention independently is carboxy, or hydrocarbyl (especially C,- 10 hydrocarbyl) carrying at least one group selected from carboxy and sulpho.
  • Hydrocarbyl groups include alkyl (especially C,-* alkyl), alkenyl (especially C 3 - 6 alkenyl), alkynyl (especially C 3 ⁇ alkynyl) and aryl (especially C 6 - 10 aryl) groups, and any combination thereof, such as aralkyl and alkaryl optionally interrupted by one or more bivalent radicals such as -CO 2 ⁇ , -CONR 1 -, -NR 1 -, -O-, -SO-, -SO 2 - or -S- wherein R 1 is H or optionally substituted C M alkyl. More preferably each D independently is carboxy, alkyl (especially C 1 alkyl) carrying at least one group selected from carboxy and sulpho or aryl carrying at least one group selected from carboxy and sulpho.
  • each D is carboxy or each D is aryl (especially phenyl) carrying at least one sulpho group.
  • n is preferably 4 to 8.
  • D is preferably aryl (especially phenyl) carrying a sulpho group.
  • a preferred compound according to the third aspect of the invention is of Formula (1) as hereinbefore defined with the provisos that M is Cu or Ni; each D is carboxy or each D is aryl (preferably phenyl) carrying at least one sulpho group; n is 4 to 8; and when all groups represented by A are N and D is carboxy, n is 1 to 7.
  • the novel compounds of Formula (1) in the third aspect of the invention are water-soluble.
  • the compounds of the present invention have attractive, strong green/cyan/blue 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. In particular the compounds of the present invention display good solubility and water-fastness.
  • a fourth aspect of the invention provides a process for printing an image on a substrate other than paper comprising applying thereto a composition according to the second aspect of the invention by means of an ink-jet printer.
  • the substrate other than paper is preferably, plastic, a textile, metal or glass, an overhead projector slide or a textile material.
  • the ink-jet printer preferably applies the composition to the substrate in an analogous manner to that as described above in relation to the first aspect of the present invention.
  • a fifth aspect of the present invention provides a substrate printed with a azaphthalocyanine compound according to a process of the first or fourth aspects of the present invention.
  • a sixth 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 in the second aspect of the present invention.
  • Benzil (42g, 0.2mol) and diaminomaleonitrile (DAMN, 21.6g, 0.2mol) were suspended in a solution of water (200ml), methylated spirit (200ml) and acetic acid (20ml). The mixture was boiled under reflux for 2 hours. After cooling a beige precipitate (56g) of 2,3-dicyano-5,6-diphenylpyrazine was collected. The sample was homogeneous by TLC.
  • stage 1 (10g, 35.5mmol) and nickel chloride (1.15g, 8.86mmol) were suspended in quinoline (100ml) and the mixture was heated to 170°C. The reaction mixture turned brown and then green. The reaction was stopped after 2 hours cooled. A solid was collected by filtration, washed with quinoline, ethanol, water and then ethanol once more to give a jade solid (4.3g).
  • the jade solid (1.5g) from stage 2 was added to a stirred solution of 10% fuming sulfuric acid (30ml) at 0°C over a period of 5-10 minutes. The mixture was stirred for 1 hour then carefully poured onto ice. Acetone (approx. 6 volume equivalents) was added and the precipitate was collected by filtration. The precipitate was taken up in water and desalted to give 1.4g of the title product having ⁇ max in water at 603 and 638 nm.
  • 2,3,5-Pyridinetricarboxylic acid (3.37g), urea (3.83g), nickel chloride (519mg), ammonium molybdate (100mg) and 1 ,2,4-trichlorobenzene (100ml) were stirred at 140°C for 1.5 hours. The temperature was raised to 165°C for a further hour and then briefly to 180°C. A deep blue coloration was noted, and the mixture left to cool, whereupon the title product was collected by filtration. The title product was washed with trichlorobenzene, ethanol and acetone and an aqueous solution of the title product was dialysed. The resultant solution of the title compound in water had ⁇ max in water at 593 and 640nm.
  • Example 4 Preparation of
  • Example 4 was prepared according to the method described by Kudrevich, Galpern and van Lier; in Synthesis (1994), page 779.
  • Inks were prepared by dissolving 3% by weight of dye in an ink vehicle comprising 5% 2- pyrrolidone, 5% thiodiglycol, 2% Suriynol 465 and the balance water. The pH was adjusted to 8.5-10 using sodium hydroxide solution (2M). The resultant inks were as follows:
  • Ink (1 ) contained the dye from Example 1.
  • Ink (2) contained the dye from Example 2.
  • Ink (3) contained the dye from Example 3.
  • Ink (4) contained the dye from Example 4. Each ink was filtered through a 0.45 ⁇ m filter and put into the chamber of a monochrome cartridge designed for the Hewlett Packard 550 printer.
  • Inks (1) to (4) were then ink-jet printed onto Xerox acid and Gilbert Bond papers using a Hewlett Packard DeskJet 550C.
  • the properties of the resultant prints are summarised in Table 1.
  • the CIE colour co-ordinates of each print (a, b, L, Chroma and hue) 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 2 measurements were taken diagonally across a solid colour block on the print with a size greater than 10mm x 10mm.
  • ⁇ E ( ⁇ L 2 + ⁇ a 2 + ⁇ b 2 ) 5 .
  • Water fastness was assessed five minutes post-printing by suspending the print at 45° and running 0.5 ml of water down a section of print comprising 12 printed lines. Each line was approximately 3 mm wide and spaced approximately 5mm apart. When the water had dried the extent of ink staining on the unprinted areas was assessed by reference to a standard scale. A value of 10 would be classed as excellent water fastness and a value of 6 would be classed as very poor water fastness.
  • the inks described in Tables I and II may be prepared wherein the Dye described in the first column is the compound 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.

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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)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)

Abstract

La présente invention concerne un processus de coloration de papier qui consiste à appliquer sur ce papier une composition comprenant un milieu et un composé azaphthalocyanine. Cette invention concerne aussi des compositions comprenant des azaphthalocyanines, de nouvelles azaphthalocyanines, un processus de coloration de substrat différent d'un substrat de papier et une cartouche d'encre pour imprimante à jet d'encre comprenant cette composition azaphthalocyanine.
PCT/GB2001/004374 2000-10-27 2001-10-01 Composition contenant une azaphthalocyanine et utilisation WO2002034844A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001292047A AU2001292047A1 (en) 2000-10-27 2001-10-01 Composition containing an azaphthalocyanine and use

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GB0026467A GB0026467D0 (en) 2000-10-27 2000-10-27 Compound, composition and use
GB0026467.1 2000-10-27

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Cited By (15)

* Cited by examiner, † Cited by third party
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JP2005220253A (ja) * 2004-02-06 2005-08-18 Konica Minolta Holdings Inc 着色組成物、インクジェット記録液およびインクジェット記録方法、カラートナー
US7097701B2 (en) 2003-12-18 2006-08-29 Fuji Photo Film Co., Ltd. Phthalocyanine compound, ink, inkjet recording method, and image forming method
US7132012B2 (en) 2004-07-15 2006-11-07 Fuji Photo Film Co., Ltd. Phthalocyanine compound, ink, ink jet recording method and image forming method
EP1741756A1 (fr) * 2003-08-27 2007-01-10 Yamamoto Chemicals, Inc. Compose tetra-azaporphyrine
WO2007091631A1 (fr) 2006-02-10 2007-08-16 Nippon Kayaku Kabushiki Kaisha Nouveau colorant porphyrazine, encre, jeu d'encre et matiere coloree
WO2007116933A1 (fr) 2006-04-07 2007-10-18 Nippon Kayaku Kabushiki Kaisha Colorant porphyrazine, encre, jeu d'encre et matiere coloree
US7300503B2 (en) 2004-07-21 2007-11-27 Fujifilm Corporation Dye mixture and ink containing the same, inkjet recording method and image forming method
WO2008111635A1 (fr) 2007-03-14 2008-09-18 Nippon Kayaku Kabushiki Kaisha Nouveau colorant porphyrazine, encre, jeu d'encres, et matière colorée de porphyrazine
CZ300906B6 (cs) * 2008-07-02 2009-09-09 Univerzita Karlova v Praze, Farmaceutická fakulta Hradec Králové Nefluoreskující deriváty ftalocyaninu a azaftalocyaninu jako zhášece fluorescence
WO2010020802A3 (fr) * 2008-08-22 2010-04-22 Fujifilm Imaging Colorants Limited Phtalocyanines et leur utilisation pour l’impression à jet d’encre
WO2010070313A2 (fr) * 2008-12-20 2010-06-24 Fujifilm Imaging Colorants Limited Azaphtalocyanines et leur application à l'impression jet d'encre
WO2010073603A1 (fr) 2008-12-25 2010-07-01 日本化薬株式会社 Colorant à la porphyrazine, composition en contenant, et matériau coloré
WO2010119676A1 (fr) 2009-04-15 2010-10-21 日本化薬株式会社 Colorant porphyrazine, composition d'encre contenant celui-ci, et corps coloré
WO2010143619A1 (fr) 2009-06-12 2010-12-16 日本化薬株式会社 Colorant porphyrazine, composition d'encre, procédé d'impression et objet coloré
CN106892927A (zh) * 2017-03-13 2017-06-27 中国石油大学(华东) 一种合成四‑2,3‑(5‑叔丁基吡嗪)金属卟啉的方法

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EP1741756A4 (fr) * 2003-08-27 2010-09-01 Yamamoto Chemicals Inc Compose tetra-azaporphyrine
EP1741756A1 (fr) * 2003-08-27 2007-01-10 Yamamoto Chemicals, Inc. Compose tetra-azaporphyrine
US7097701B2 (en) 2003-12-18 2006-08-29 Fuji Photo Film Co., Ltd. Phthalocyanine compound, ink, inkjet recording method, and image forming method
JP2005220253A (ja) * 2004-02-06 2005-08-18 Konica Minolta Holdings Inc 着色組成物、インクジェット記録液およびインクジェット記録方法、カラートナー
US7132012B2 (en) 2004-07-15 2006-11-07 Fuji Photo Film Co., Ltd. Phthalocyanine compound, ink, ink jet recording method and image forming method
US7300503B2 (en) 2004-07-21 2007-11-27 Fujifilm Corporation Dye mixture and ink containing the same, inkjet recording method and image forming method
WO2007091631A1 (fr) 2006-02-10 2007-08-16 Nippon Kayaku Kabushiki Kaisha Nouveau colorant porphyrazine, encre, jeu d'encre et matiere coloree
WO2007116933A1 (fr) 2006-04-07 2007-10-18 Nippon Kayaku Kabushiki Kaisha Colorant porphyrazine, encre, jeu d'encre et matiere coloree
WO2008111635A1 (fr) 2007-03-14 2008-09-18 Nippon Kayaku Kabushiki Kaisha Nouveau colorant porphyrazine, encre, jeu d'encres, et matière colorée de porphyrazine
CZ300906B6 (cs) * 2008-07-02 2009-09-09 Univerzita Karlova v Praze, Farmaceutická fakulta Hradec Králové Nefluoreskující deriváty ftalocyaninu a azaftalocyaninu jako zhášece fluorescence
WO2010020802A3 (fr) * 2008-08-22 2010-04-22 Fujifilm Imaging Colorants Limited Phtalocyanines et leur utilisation pour l’impression à jet d’encre
US8529685B2 (en) 2008-08-22 2013-09-10 Fujifilm Imaging Colorants Limited Azaphthalocyanines and their use in ink-jet printing
WO2010070313A2 (fr) * 2008-12-20 2010-06-24 Fujifilm Imaging Colorants Limited Azaphtalocyanines et leur application à l'impression jet d'encre
WO2010070313A3 (fr) * 2008-12-20 2010-08-26 Fujifilm Imaging Colorants Limited Azaphtalocyanines et leur application à l'impression jet d'encre
US8702854B2 (en) 2008-12-20 2014-04-22 Fujifilm Corporation Azaphthalocyanines and their use in ink-jet printing
KR20110112805A (ko) 2008-12-25 2011-10-13 니폰 가야꾸 가부시끼가이샤 포르피라진 색소, 이를 함유하는 잉크 조성물 및 착색체
WO2010073603A1 (fr) 2008-12-25 2010-07-01 日本化薬株式会社 Colorant à la porphyrazine, composition en contenant, et matériau coloré
WO2010119676A1 (fr) 2009-04-15 2010-10-21 日本化薬株式会社 Colorant porphyrazine, composition d'encre contenant celui-ci, et corps coloré
KR20120022771A (ko) 2009-04-15 2012-03-12 니폰 가야꾸 가부시끼가이샤 포르피라진 색소, 이를 함유하는 잉크 조성물 및 착색체
WO2010143619A1 (fr) 2009-06-12 2010-12-16 日本化薬株式会社 Colorant porphyrazine, composition d'encre, procédé d'impression et objet coloré
US8657433B2 (en) 2009-06-12 2014-02-25 Nippon Kayaku Kabushiki Kaisha Porphyrazine coloring matter, ink composition, recording method, and colored object
CN106892927A (zh) * 2017-03-13 2017-06-27 中国石油大学(华东) 一种合成四‑2,3‑(5‑叔丁基吡嗪)金属卟啉的方法
CN106892927B (zh) * 2017-03-13 2019-03-01 中国石油大学(华东) 一种合成四-2,3-(5-叔丁基吡嗪)金属卟啉的方法

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