WO2007018232A1 - Composé monoazoïque, composition d’encre et objet coloré - Google Patents

Composé monoazoïque, composition d’encre et objet coloré Download PDF

Info

Publication number
WO2007018232A1
WO2007018232A1 PCT/JP2006/315726 JP2006315726W WO2007018232A1 WO 2007018232 A1 WO2007018232 A1 WO 2007018232A1 JP 2006315726 W JP2006315726 W JP 2006315726W WO 2007018232 A1 WO2007018232 A1 WO 2007018232A1
Authority
WO
WIPO (PCT)
Prior art keywords
ink
group
ink composition
salt
recording
Prior art date
Application number
PCT/JP2006/315726
Other languages
English (en)
Japanese (ja)
Inventor
Shinjirou Takahashi
Yoshiyuki Dejima
Takahiko Matsui
Original Assignee
Nippon Kayaku Kabushiki Kaisha
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 Nippon Kayaku Kabushiki Kaisha filed Critical Nippon Kayaku Kabushiki Kaisha
Priority to JP2007529605A priority Critical patent/JPWO2007018232A1/ja
Publication of WO2007018232A1 publication Critical patent/WO2007018232A1/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
    • C09D11/322—Pigment inks
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • 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

Definitions

  • the present invention relates to a monoazo compound or a salt thereof, an ink composition containing the same, and a colored product obtained using the same.
  • the recording method using an ink jet printer which is one of the representative methods, has developed various ink ejection methods, all of which generate ink droplets. Is recorded on various recording materials (paper, film, fabric, etc.). In this method, the recording head does not come into direct contact with the recording material, so there is no sound generation, and it is quiet. In addition, due to the features of miniaturization and easy high-speed operation, it has been rapidly spreading in recent years, and will continue to increase in the future. Expected to grow.
  • inks such as fountain pens and felt pens, and inks for ink jet recording have been used inks in which water-soluble dyes are dissolved in aqueous media.
  • a water-soluble organic solvent is generally added to prevent ink clogging.
  • These inks provide a recorded image with sufficient density, do not cause clogging of the pen tip and nozzles, good drying on the recording material, low bleeding, and storage stability. It is required to be excellent, and the formed image is required to have fastness such as water resistance, moisture resistance, light resistance and gas resistance.
  • the ink composition is required to be stable against long-term storage, to have a high density of printed images, and to be excellent in fastness such as water resistance, moisture resistance, light resistance and gas resistance.
  • Gas resistance Tolerance is the resistance to the phenomenon of wrinkles when ozone gas, etc. that has an acidic action in the air reacts with the dye on the recording paper or in the recording paper to discolor the printed image.
  • ozone gas is considered to be a main causative substance that promotes the fading phenomenon of ink jet recorded images. Since this discoloration phenomenon is characteristic of ink jet images, improvement of ozone gas resistance is an important issue in the technical field of ink jet recording.
  • Examples of the skeleton of the yellow dye for inkjet which is excellent in water solubility and sharpness include CI (color index) acid yellow 23 of a pyrazolone monoazo dye represented by the following formula (2) (for example, see Patent Documents 1 to 4).
  • CI color index
  • Patent Document 5 discloses that a pyrazolone monoazo compound obtained by coupling dicarboline-phosphorus to a pyrazolone is used for inkjet printing, and has excellent ink storage stability and light resistance. Is disclosed. However, there is no disclosure of dyes with excellent ozone resistance and moisture resistance.
  • Patent Document 6 also describes a force that describes a pyrazolone-based monoazo compound.
  • the ink jet print is not touched, and the description of the performance required for inkjet printing such as ozone resistance and moisture resistance is as follows. I ca n’t see it. [0005]
  • Patent Document 1 JP 2000-178492 A
  • Patent Document 2 JP 2002-241648
  • Patent Document 3 JP 2002-53780
  • Patent Document 4 JP 2002-226739
  • Patent Document 5 JP 2003-286420 A
  • Patent Document 6 British Patent Gazette 753, 550
  • the present invention has a hue and sharpness suitable for ink jet recording with high solubility in water, and the recorded material has fastness such as water resistance, moisture resistance, light resistance and gas resistance.
  • An object is to provide excellent dyes (compounds), particularly yellow dyes, and ink compositions containing the same.
  • a monoazo compound represented by the following formula (1) or a salt thereof (In the formula, R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, Y is a carboxyl group,
  • Y represents a hydroxyl group or an amino group.
  • R is a hydrogen atom
  • Y is a carboxyl group
  • X is hydrogen
  • An ink composition comprising the monoazo compound or salt thereof according to (1) or (2) as a dye component,
  • an inkjet recording method for recording on a recording material by ejecting ink droplets according to a recording signal the ink composition according to any one of (3) to (5)
  • An ink jet recording method comprising using an ink composition
  • the monoazo compound of the formula (1) or a salt thereof of the present invention is excellent in water solubility, has good filterability with respect to a membrane filter during the production of an ink composition, and is very clear on an ink jet recording paper. It has the characteristics that it shows a hue with high brightness and excellent fastness. That is, the ink composition of the present invention using the compound of the present invention has good storage stability without crystal precipitation, physical property change, color change, etc. after long-term storage, and was obtained using this ink composition.
  • the printed material has an ideal hue without selecting a recording material (paper, film, etc.), and it is possible to faithfully realize the hue of a photographic color image on paper.
  • the monoazo compound of the present invention is represented by the following formula (1) in the form of a free acid.
  • R represents a hydrogen atom and an alkyl group having 1 to 4 carbon atoms.
  • Y represents a carboxyl group
  • Y represents a hydroxyl group or an amino group.
  • X is the hydrogen source
  • N represents an integer of 1 to 3, each of a hydrogen atom, a halogen atom, a sulfo group, a sulfamoyl group, a hydroxyl group or a -tro group.
  • the alkyl group having 1 to 4 carbon atoms for R in the formula (1) includes a methyl group, an ethyl group, n-
  • Examples include propyl group, iso propyl group, n butyl group, iso butyl group, sec butyl group and t butyl group, and methyl group is preferred.
  • X is a halogen atom
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Is most preferred.
  • Preferred R, Y, Y, X and ⁇ in the formula (1) are a hydrogen atom, carboxy, respectively.
  • R is a hydrogen atom, ⁇ , ⁇ , and! ! But
  • a combination of the same groups as in formula (1) more preferably a case where R is a hydrogen atom, ⁇ is a carboxyl group or a ⁇ ⁇ ⁇ ⁇ ⁇ hydroxy group, and X and ⁇ are the same groups as in formula (1).
  • R 1, ⁇ and ⁇ represent the same groups as in formula (1),
  • X is a hydrogen atom, ⁇ is 2, and preferably two carboxyl groups are substituted at the 3 and 5 positions.
  • a more preferable combination in this combination is when ⁇ is a carboxyl group and a strong S-hydroxy group.
  • R is a hydrogen atom or
  • 1 1 2 1 is methyl group
  • Y is carboxyl group
  • X is hydrogen atom
  • n is 2
  • R is a hydrogen atom
  • Y is a hydrogen atom
  • 1 1 is a carboxyl group, Y force hydroxyl group, X is a hydrogen atom, and n is 2.
  • substitution position of the two carboxyl groups represented by — (COOH) n is particularly preferably in the 3rd and 5th positions relative to the bonding position of pyrazolone to the nitrogen atom.
  • the compound of the formula (1) is preferably used as an inorganic or organic cation salt.
  • the salt include lithium salt, sodium salt, potassium salt, and an ammonium salt represented by the formula (4). Etc.
  • X to X each independently represent a hydrogen atom, an alkyl group, or a hydroxyalkyl group.
  • Examples of the alkyl group in X to X in the formula (4) include a methyl group and an ethyl group.
  • hydroxyalkyl groups include hydroxymethyl group, hydroxyethyl group, 3-hydroxypropyl group, 2-hydroxypropyl group, 4-hydroxybutyl group, 3-hydroxybutyl group, 2-hydroxybutyl group, etc.
  • hydroxyalkoxyalkyl groups include hydroxyethoxymethyl group, 2-hydroxyethoxyethyl group, 3- (hydroxyethoxy) propyl group, 3- (hydroxyethoxy) butyl group, 2- ( And hydroxyethoxy) butyl group.
  • Salt, ammonium salt and the like are particularly preferable salts.
  • each of the above-mentioned salts can be easily obtained as follows.
  • the sodium salt of a dye can be obtained as a wet cake by adding salt to the reaction solution at the time of dye synthesis, or a wet cake containing the dye or a dried product dissolved in water, salting out, and filtering. Can do.
  • a free acid of the dye or a mixture of free acid and sodium salt can be obtained.
  • the mixing ratio of the free acid and sodium salt can be arbitrarily adjusted by adding hydrochloric acid and appropriately adjusting the pH from the alkali side to the acid side.
  • the salt other than the sodium salt for example, potassium hydroxide, lithium hydroxide, ammonia water or water of the formula (4) is used while stirring the obtained free acid wet cake with water. If it is made alkaline by adding an oxide, etc., the corresponding potassium salt, lithium salt, ammonia Nyum salt, 4th grade ammonium salt can be obtained.
  • the mixture of the free acid and sodium salt is similarly treated with stirring in water to give the corresponding sodium salt and other potassium, lithium, ammonium, quaternary ammonia. It is also possible to easily obtain mixed salts such as
  • the monoazo compound represented by the formula (1) of the present invention can be produced, for example, as follows.
  • an aromatic amine represented by the following formula (5) is diazotized by a conventional method, and a coupler represented by the following formula (6) is used at room temperature (usually 20 to 25 ° C), neutral to weakly alkaline (usually P It can be obtained by coupling reaction with H7-8).
  • the monoazo compound of the present invention is suitable for dyeing natural and synthetic fiber materials or blended products, and these compounds are suitable for the production of ink compositions for writing and ink compositions for ink jet recording. ! / Speak.
  • the reaction liquid containing the monoazo compound of formula (1) of the present invention can be used directly in the production of an ink composition. However, it can also be isolated from the reaction solution, dried, for example spray dried, and then processed into an ink composition.
  • the recording ink composition of the present invention usually contains 0.1 to 20% by mass, preferably 1 to 15% by mass, and more preferably 2 to 10% by mass of the monoazo compound of the present invention in an aqueous solution.
  • the water-soluble organic solvent is usually 0 to 30% by mass, preferably 5 to 30% by mass
  • the ink preparation agent is usually 0 to: L0% by mass, preferably 1 to 7% by mass. In some cases, 0 to 5% by mass is contained.
  • the balance is water.
  • C1-C4 alkanol carboxylic acid amides such as N, N-dimethylformamide or N, N-dimethylacetamide, ratatams such as 2-pyrrolidone and N-methyl-2-pyrrolidone, 1,3-dimethylimidazolid Cyclic ureas such as N-2-one or 1,3-dimethylhexahydropyrimido-2-one, acetone, methylethyl Ketones, ketones such as 2-methyl-2-hydroxypentane-4-one or ketoalcohols, cyclic ethers such as tetrahydrofuran, dioxane, ethylene glycol, 1,2- or 1,3 propylene glycol, 1,2 or 1,4 butylene glycol, 1, 6 Hexylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, thiodiglycol glycol, polyethylene glycol, polypropylene glycol and other monomers,
  • 2-pyrrolidone 2-methyl-2-pyrrolidone, mixed di- or triethylene glycol, dipropylene glycol, and butyl carbitol are preferable, and 2-pyrrolidone, 2-methyl-2-pyrrolidone, Diethylene glycol or butyl canolebitonore.
  • the ink preparation agents for example, an antiseptic and fungicide, [rho Eta adjusting agents, chelating agents, anti ⁇ , water-soluble ultraviolet absorber, water-soluble polymer compound, a dye dissolving agent, such as surfactants like et be.
  • an antiseptic and fungicide [rho Eta adjusting agents, chelating agents, anti ⁇ , water-soluble ultraviolet absorber, water-soluble polymer compound, a dye dissolving agent, such as surfactants like et be.
  • antiseptic / antifungal agents examples include organic sulfur-based, organic nitrogen-sulfur-based, organic halogen-based, noro-arinores norephone-based, odopropagnole-based, ⁇ ⁇ haloanorequinolethio-based, -trinore-based, Pyridine, 8-oxyquinoline, benzothiazole, isothiazoline, dithiol, pyridine oxide, nitropropane, organotin, phenol, quaternary ammonium salt, triazine, thiadiazine, anilide , Adamantane, dithiocarbamate, bromoindanone, benzyl bromacetate, inorganic salt, and the like.
  • Examples of the organic halogen compound include pentachlorophenol sodium, and examples of the pyridine oxide compound include 2-pyridinethiol.
  • Other antiseptic and antifungal agents include sodium sorbate sodium benzoate and the like.
  • any substance can be used as long as it can control the pH of the ink composition to a range of usually 7.0 to L 1.0 without adversely affecting the ink composition to be prepared.
  • pH adjusters include alkanolamines such as diethanolamine and triethanolamine, and alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide. , Ammonium hydroxide, or alkali metal carbonates such as lithium carbonate, sodium carbonate, and potassium carbonate.
  • Examples of the chelate reagent include sodium ethylenediamine tetraacetate, sodium nitrite triacetate, sodium hydroxyethylethylenediamine triacetate, sodium diethylenetriaminepentaacetate, sodium uracil diacetate and the like.
  • Examples of the antifungal agent include acidic sulfites, sodium thiosulfate, ammonium thioglycolate, diisopropyl ammonium nitrite, pentaerythritol tetranitrate, and dicyclohexyl ammonium nitrite.
  • Examples of the water-soluble ultraviolet absorber include sulfonated benzophenone or sulfonated benzotriazole.
  • Examples of the water-soluble polymer compound include polyvinyl alcohol, cellulose derivatives, polyamines and polyimines.
  • Examples of the dye solubilizer include urea, epsilon prolactam, ethylene carbonate, and the like.
  • Examples of the surfactant include a char-on surfactant, an amphoteric surfactant, a cationic surfactant, and a no-one surfactant.
  • cation surfactants include alkyl sulfocarboxylates, ⁇ -olefin sulfonates, polyoxyethylene alkyl ether acetates, acyl amino acids and their salts, and acyl methyl taurate.
  • Examples of cationic surfactants include 2-bulupyridine derivatives and poly-4-bulupyridine derivatives.
  • Amphoteric surfactants include lauryl dimethylamino acetate betaine, 2-alkyl mono-N-carboxymethyl-N-hydroxyethyl imidazolium umbetaine, coconut oil fatty acid aminopropyl dimethylamino acetate betaine, poly Octylpolyaminoethylglycine and other imidazoline derivatives.
  • Nonionic surfactants include polyoxyethylene norphenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene decyl phenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene oleyl ether, Ethers such as polyoxyethylene lauryl ether, polyoxyethylene alkyl ether, polyoxyethylene oleic acid, polyoxyethylene oleate, polyoxyethylene distearate, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, Sonorbitan sesquioleate, ester compounds such as polyoxyethylene monooleate, polyoxyethylene stearate, 2, 4, 7, 9-tetramethyl-5-decyne-4,7-di Acetylene glycols such as all, 3, 6-dimethyl 4-octyne-3, 6-diol, 3, 5-dimethyl-1, monohexyne-3-ol (for example, Surfin
  • the ink composition of the present invention can be produced by dissolving a monoazo compound represented by the formula (1) in water or a mixture of water and the water-soluble organic solvent together with the ink preparation agent.
  • the reaction liquid of the monoazo compound of formula (1) is used directly in the production of an ink composition, the content of inorganic substances such as metal cation salts and sulfates as impurities is reduced. It is preferable to use a small amount.
  • the standard of the content is, for example, the content in a monoazo compound (pure component). It is about 1% by mass or less.
  • a desalting treatment may be performed, for example, by a method using a reverse osmosis membrane.
  • the monoazo compound represented by the formula (1) is dissolved in water and Z or a water-soluble organic solvent in advance, and the ink preparation agent is added and dissolved, and the formula (1) is represented. After the monoazo compound is dissolved in water, a water-soluble organic solvent and an ink preparation agent may be added and dissolved. The order may be different from this, but the reaction solution of the monoazo compound represented by the formula (1) or the solution subjected to the desalting treatment by the reverse osmosis membrane may be mixed with a water-soluble organic solvent or an ink preparation. An ink composition may be produced by adding a preparation.
  • the water used is preferably an ion-exchanged water or distilled water with few impurities.
  • the ink composition is prepared and used as an ink for an ink jet printer in which fine filtration may be performed using a membrane filter or the like to remove impurities, if necessary, fine filtration is preferably performed.
  • the pore size of the filter is usually 1 micron to 0.1 micron, preferably 0.8 micron to 0.2 micron.
  • the ink composition containing the monoazo compound of the present invention is used as an ink composition for yellow in printing, copying, marking, writing, drawing, stamping, or recording methods, particularly in inkjet recording. Suitable. In this case, a high-quality yellow print with good resistance to water, sunlight, ozone and friction can be obtained.
  • the colored product of the present invention is colored with the compound of the present invention.
  • the material to be colored include, but are not limited to, paper, fiber, cloth (cellulose, nylon, wool, etc.), leather, color filter base material, and the like.
  • a printing method such as a dip dyeing method, a textile printing method, a screen printing method, a method S using an ink jet printer, and a method using an ink jet printer are preferable.
  • Some inkjet printers are set with two types of ink, a high-density ink and a low-density ink, for the purpose of supplying a high-definition image.
  • a high-density ink and a low-density ink are produced using the monoazo compound represented by the formula (1) of the present invention, and the ink set can be used in combination.
  • an ink containing a monoazo compound represented by the formula (1) may be used for only one of them.
  • the module represented by the formula (1) of the present invention is also used.
  • a noazo compound may be used in combination with a known yellow dye.
  • the monoazo compound represented by formula (1) is used in order to adjust the hue of other colors, such as black dye, or to mix with magenta dye or cyan dye to prepare red ink or green ink.
  • the monoazo compound represented by formula (1) is used. Use as a toning component.
  • a recording material (medium) to which the ink jet recording method of the present invention can be applied for example, paper
  • the information transmission sheet is preferably a surface-treated sheet, specifically, an ink receiving layer provided on these substrates.
  • the ink-receptive layer is formed by, for example, impregnating or coating the above-mentioned base material with a cationic polymer, or by converting a porous white inorganic substance capable of absorbing the pigment in the ink, such as porous silica, alumina sol or special ceramics, into polybutyl alcohol. It is provided by coating the surface of the substrate together with a hydrophilic polymer such as polypyrrole pyrrolidone.
  • a paper provided with such an ink receiving layer is usually called an inkjet paper (film) or glossy paper (film).
  • Pictorico Aligni Glass Co., Ltd.
  • color BJ paper color BJ photo film sheet
  • professional photo Paper both manufactured by Canon Inc.
  • color image jet paper manufactured by Sharp Corporation
  • PM photographic paper Super Fine Fine Gloss Film (, deviation is also manufactured by Epson Corporation)
  • Picta Fine manufactured by Hitachi Maxell Corporation
  • it can also be used for plain paper.
  • an image recorded on a recording material coated with a porous white inorganic material on the surface is particularly known to be discolored by ozone gas.
  • the ink composition of the present invention has gas resistance. Because it excels, it is particularly effective when recording on such recording materials.
  • a container containing the ink composition described above is set at a predetermined position of an ink jet printer, and is recorded on the recording material by a normal method. Record it.
  • the water-based yellow ink composition, magenta ink composition, cyan ink composition of the present invention, and if necessary, a green ink composition, a blue (or violet) ink composition, a red ink composition And a black ink composition is stored in its own container.
  • the container is loaded into a predetermined position of the ink jet printer and used.
  • the ink jet printer include a piezo printer using mechanical vibration and a bubble jet (registered trademark) printer using bubbles generated by heating.
  • the ink composition of the present invention has a clear yellow color, and has a hue suitable for inkjet recording, which is particularly sharper than inkjet glossy paper. In addition, the fastness of recorded images is very high.
  • the ink composition of the present invention does not precipitate or separate during storage. Further, when the ink composition of the present invention is used in ink jet recording, the ejector (ink head) is not blocked.
  • the ink composition according to the present invention does not cause changes in physical properties even under constant recirculation for a relatively long time by a continuous ink jet printer or intermittent use by an on-demand ink jet printer.
  • reaction solution was filtered, and the filtrate was completely dried with a hot air dryer (80 ° C.) to obtain 50.0 parts of a reaction product dye powder.
  • This powder was put into a mixture of 200 parts of water and 450 parts of methanol, stirred for 1 hour and then filtered.
  • the obtained wet cake was completely dried with a hot air dryer (80 ° C) to obtain 44.0 parts of the monoazo compound of the present invention represented by the formula (8) ( ⁇ max 412 nm in water). .
  • a liquid having the composition shown in Table 2 was prepared using the compound obtained in Example 1 and filtered through a 0.45 / zm membrane filter to obtain an ink composition of the present invention for ink jet recording.
  • the water in the table was ion exchange water.
  • water was added so that the total amount would be 100 parts.
  • Table 2 Composition of ink composition
  • N-methyl-2-pyrrolidone 4.0 parts isopropyl alcohol 3.0 parts butyl carbitol 2.0 parts Surfinols 104 PG 50 0.1 part ammonia water + water 77.9 parts total 100.0 parts
  • CI ink yellow 23 represented by the above formula (2) which is widely used as an inkjet yellow pigment, was prepared as a comparative ink composition according to Example 2 using the composition shown in Table 3. did.
  • the test conducted using the obtained ink composition is referred to as Comparative Example 1.
  • Table 3 Composition of ink composition
  • the light resistance test and the ozone gas resistance test were performed on the portion (test specimen) where the reflection density D value of the printed material before the test was closest to 1.
  • the reflection density was measured using a GRETAG SPM50 (color measurement system, manufactured by GRETAG).
  • OHKEN RTH-35DX Constant temperature and humidity chamber, manufactured by Applied Giken Sangyo Co., Ltd.
  • the sample was left for 7 days at 90% RH, and the bleeding of the dye (compound) in the image patterns before and after the test was judged by visual feeling.
  • Comparative Example 1 shows a significant amount of dye bleeding, whereas the image pattern of Example 2 shows almost no bleeding.
  • the recorded image using the dye of the present invention is extremely excellent in moisture resistance.
  • the specimen is irradiated with Ci4000 (Xenon Weatherometer, manufactured by ATLAS) at 0.336 W / square meter illumination for 50 hours, and the reflection density ratio before and after the test (reflection OD value after test I reflection before test) OD value X 100) was determined and used as the residual rate (%) of each dye (compound) after the test.
  • Ci4000 Xenon Weatherometer, manufactured by ATLAS
  • ⁇ Survival rate is 80% or more.
  • ⁇ Residual rate is 70% or more and less than 80.
  • X Residual rate is less than 70%.
  • the dye residual ratio of Comparative Example 1 was less than 70% in any glossy paper, whereas in Example 2, the dye residual ratio was 80% or more.
  • the recorded image using the dye of the present invention is extremely light-fast but has extremely excellent fastness.
  • the test piece was allowed to stand for 3 hours in an ozone weather meter (manufactured by Suga Test Instruments Co., Ltd.) in an environment with an ozone concentration of 40 ppm, a humidity of 60% RH, and a temperature of 24 ° C.
  • an ozone weather meter manufactured by Suga Test Instruments Co., Ltd.
  • the reflection density ratio (%) after 3 hours was determined, and the residual ratio (%) of each compound after the test. was calculated.
  • ⁇ Survival rate is 70% or more.
  • ⁇ Residual rate is 60% or more and less than 70.
  • X Residual rate is less than 60%.
  • the ink composition using the monoazo compound of the present invention is extremely excellent in moisture resistance, light resistance, and ozone gas resistance, and is very useful as a yellow pigment for inkjet ink compositions. It turns out that it is a useful compound.

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

La présente invention concerne un composé monoazoïque représenté par la formule (1) : (dans laquelle R1 représente un atome d’hydrogène ou un groupe alkyle en C1 à C4 ; Y1 représente un groupe carboxy, méthyle ou phényle ; et Y2 représente un groupe hydroxy ou amino) ou un sel du composé ; une composition d’encre contenant le composé ou son sel ; et un objet coloré qui a été coloré par n'importe lequel de ses composés. La composition d’encre contenant le composé a une grande stabilité lors du stockage. Une copie obtenue par une impression avec le composé possède une grande clarté et une forte solidité en ce qui concerne la résistance à l'humidité, la résistance à l'ozone, la résistance à une lampe au xénon, etc.
PCT/JP2006/315726 2005-08-11 2006-08-09 Composé monoazoïque, composition d’encre et objet coloré WO2007018232A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2007529605A JPWO2007018232A1 (ja) 2005-08-11 2006-08-09 モノアゾ化合物、インク組成物及び着色体

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005-233359 2005-08-11
JP2005233359 2005-08-11

Publications (1)

Publication Number Publication Date
WO2007018232A1 true WO2007018232A1 (fr) 2007-02-15

Family

ID=37727415

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2006/315726 WO2007018232A1 (fr) 2005-08-11 2006-08-09 Composé monoazoïque, composition d’encre et objet coloré

Country Status (3)

Country Link
JP (1) JPWO2007018232A1 (fr)
TW (1) TW200720362A (fr)
WO (1) WO2007018232A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB837716A (en) * 1957-03-15 1960-06-15 Sandoz Ltd Improvements in or relating to monoazo dyestuffs derived from aminopyrazoles and their metal complex compounds
JP2003286420A (ja) * 2002-03-28 2003-10-10 Mitsui Chemicals Inc 水性インク
JP2005350600A (ja) * 2004-06-11 2005-12-22 Nippon Kayaku Co Ltd 水溶性モノアゾ化合物、インク組成物および着色体
JP2006096855A (ja) * 2004-09-29 2006-04-13 Nippon Kayaku Co Ltd 水溶性アゾ化合物、インク組成物および着色体

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB837716A (en) * 1957-03-15 1960-06-15 Sandoz Ltd Improvements in or relating to monoazo dyestuffs derived from aminopyrazoles and their metal complex compounds
JP2003286420A (ja) * 2002-03-28 2003-10-10 Mitsui Chemicals Inc 水性インク
JP2005350600A (ja) * 2004-06-11 2005-12-22 Nippon Kayaku Co Ltd 水溶性モノアゾ化合物、インク組成物および着色体
JP2006096855A (ja) * 2004-09-29 2006-04-13 Nippon Kayaku Co Ltd 水溶性アゾ化合物、インク組成物および着色体

Also Published As

Publication number Publication date
JPWO2007018232A1 (ja) 2009-02-19
TW200720362A (en) 2007-06-01

Similar Documents

Publication Publication Date Title
JP4794241B2 (ja) 水溶性アゾ化合物、インク組成物及び着色体
JP5979728B2 (ja) 水性黒色インク組成物、これを用いるインクジェット記録方法、及び着色体
WO2007020719A1 (fr) Composés azoïques hydrosolubles, compositions d’encre et produits colorés
WO2007049366A1 (fr) Compose azoique hydrosoluble, composition d’encre et materiau colore
WO2011122426A1 (fr) Composé azo hydrosoluble ou sel de ce composé, composition d'encre, et corps coloré
WO2006051850A1 (fr) Composé azoïque, composition d'encre et matière colorante
WO2006075706A1 (fr) Compose d'anthrapyridone, encre magenta et matiere colorante
JP2008088281A (ja) 水溶性アゾ化合物又はその塩、インク組成物及び着色体
JP4794270B2 (ja) 水溶性アゾ化合物、インク組成物および着色体
JP2008088282A (ja) 水溶性アゾ化合物又はその塩、インク組成物及び着色体
JP4974682B2 (ja) 新規アゾ化合物または塩、そのアゾ化合物を含有するインク組成物及び着色体
JP2013018849A (ja) 水溶性アゾ化合物又はその塩、インク組成物及び着色体
WO2010146994A1 (fr) Composé azoïque hydrosoluble ou sel de celui-ci, composition d'encre et corps coloré
JP2008056830A (ja) 水溶性アゾ化合物又はその塩、インク組成物及び着色体
WO2007018175A1 (fr) Composé d'anthrapyridone et sel de celui-ci, composition d'encre magenta contenant un tel composé d'anthrapyridone et corps coloré
KR20080043787A (ko) 아조 화합물, 잉크 조성물, 기록방법 및 착색체
JP4963883B2 (ja) 水溶性アゾ化合物又はその塩、インク組成物及び着色体
JP4404308B2 (ja) 水溶性モノアゾ化合物、インク組成物および着色体
WO2007018232A1 (fr) Composé monoazoïque, composition d’encre et objet coloré
JP4888949B2 (ja) アゾ色素またはその塩、該アゾ色素またはその塩を含有する水性オレンジインク組成物
JP2018127592A (ja) アゾ化合物又はその塩、インク組成物及び着色体
JP4408734B2 (ja) 水溶性モノアゾ化合物を含有する水性インク組成物及びこれを用いるインクジェット記録方法
JP2018065919A (ja) 水溶性アゾ化合物又はその塩、インク組成物及び着色体
JP2006096855A (ja) 水溶性アゾ化合物、インク組成物および着色体
JP2005042028A (ja) 水溶性モノアゾ化合物、それを含有する水性オレンジインク組成物及びこれを用いて得られる着色体

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2007529605

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 06782542

Country of ref document: EP

Kind code of ref document: A1