WO2005108502A1 - テトラキスアゾ化合物、記録用色素、インク組成物及び着色体 - Google Patents
テトラキスアゾ化合物、記録用色素、インク組成物及び着色体 Download PDFInfo
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- WO2005108502A1 WO2005108502A1 PCT/JP2005/008438 JP2005008438W WO2005108502A1 WO 2005108502 A1 WO2005108502 A1 WO 2005108502A1 JP 2005008438 W JP2005008438 W JP 2005008438W WO 2005108502 A1 WO2005108502 A1 WO 2005108502A1
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Classifications
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- 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/18—Trisazo or higher polyazo dyes
- C09B33/28—Tetrazo dyes of the type A->B->K<-C<-D
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
- B41J2/01—Ink jet
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
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- 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
- 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
Definitions
- Tetrakisazo compound recording dye, ink composition and colored body
- the present invention relates to a novel water-soluble tetrakisazoi conjugate or a salt thereof, a recording dye, an ink composition containing the same, and a colored product thereof.
- Dyes exhibiting black are used not only for printing black character information but also for color images.
- the development of a dye having a hue of -Eutral and a high density of black is technically difficult, and a great deal of research and development has been carried out, but few of them have sufficient performance.
- a variety of dyes are mixed to form black, but the development of dyes that exhibit a high concentration -Eutral black by themselves alone is the most strongly demanded at present. This is a technical issue.
- a recording method using an ink jet printer which is one of the representative methods, generates small ink droplets and attaches them to various recording materials (paper, film, fabric, etc.) to record. Is what you do. This method has been rapidly spreading in recent years due to the fact that the recording head does not come into contact with the recording material and generates less noise and is quiet. Is expected.
- aqueous inks in which a water-soluble dye is dissolved in an aqueous medium have been used as inks for fountain pens, felt pens, etc. and ink jet recording inks.
- a water-soluble organic solvent is added to prevent clogging of the ink at the nozzles.
- the formed image is required to have image fastness such as water fastness, light fastness, ozone gas fastness, and moisture fastness.
- Ozone gas resistance is a force that is also called ozone resistance or gas resistance. It is the resistance of the existing oxidizing ozone gas to the phenomenon of reacting with the dye in the recording paper and discoloring the printed image.
- NOx, SOx and the like are examples of oxidizing gases having this kind of action.
- ozone gas power S is considered to be a substance that further promotes the discoloration and fading phenomenon of ink jet recorded images.
- Ozone gas is used in an acceleration test to determine the degree of ozone gas resistance. V, being, being. Since the discoloration and fading due to the oxidizing gas are characteristic of the ink jet image, improvement of the ozone gas resistance has become a more important issue.
- the ink receiving layer provided on the surface of photographic quality inkjet paper is made of a porous material such as a white inorganic pigment to accelerate drying of the ink and reduce bleeding with high image quality.
- the moisture resistance refers to the resistance to the phenomenon of bleeding of the dye and dye in the recording material when the colored recording material is stored in a high-humidity atmosphere. If there is bleeding of the dye color, the quality of the image is remarkably reduced particularly in an image requiring high definition image quality such as a photographic tone. Therefore, it is important to reduce such bleeding as much as possible.
- moisture resistance is also an important issue required for ink jet dyes, similar to the above-mentioned ozone gas resistance.
- the ink composition used for ink-jet recording which will expand the field of use of the printing method using ink, and the colored body colored by the ink composition will have water resistance, light resistance, moisture resistance, and ozone gas resistance.
- Patent Documents 1 to 3 have been proposed as tetrakisazoi conjugates having an increased number of conjugated bonds, but they have not yet supplied products that sufficiently satisfy market requirements.
- Patent Document 1 JP-A-8-302220
- Patent Document 2 JP-A-8-302221
- Patent Document 3 JP-A-9-12910
- Patent Document 4 Patent No. 2565531
- Patent Document 5 JP 2003-286421
- Patent Document 6 International Publication WO00Z43451 pamphlet
- Patent document 7 International publication WO00Z43453 pamphlet
- the present invention is stable even when a high-concentration aqueous dye solution and ink having high solubility in a medium containing water as a main component are stored for a long period of time, exhibits a neutral black color with no color, and A black dye with a high density printed image gives a black recorded image with excellent moisture resistance, light resistance and ozone gas resistance, and a black dye and its ink composition that are easy to synthesize and inexpensive
- the purpose is to provide things.
- a and D are each independently substituted with each other and represent a phenyl group or a naphthyl group, and m and n each represent 1 or 2)
- m ′ and n ′ each represent 1, the substitution position of the sulfo group is the 4-position and the 8-position, respectively, the bonding position of the bond a is the 3-position, the compound or the recording dye according to the above (2), wherein the bonding position of b is 7-position;
- Substituent force on A and D in formula (1) or (2) Halogen atom; hydroxyl group; amino group; carboxyl group; sulfo group; phosphono group; nitro group; alkyl group; A silyl group; a phenyl group; a ureido group; an alkyl group substituted with a hydroxyl group, an alkoxy group, a sulfo group or a carboxyl group; an alkoxy group substituted with a hydroxyl group, an alkoxy group, a sulfo group or a carboxyl group.
- the above-mentioned (1) or (b), which is substituted by a carboxy group or a sulfo group, may be a phenyl group; substituted by an alkyl group or an acyl group, and is a amino group; a benzothiazole group; a mesyl group; Is the recording dye according to (2),
- a and D each independently represent a halogen atom, a carboxyl group, a sulfo group, a nitro group, an alkoxy group, a sulfoalkoxy group, an acylamino group, a benzothiazole group, a mesyl group or
- a and D in the formula (2) each have a sulfo group or a carboxyl group at the 2-position to the azo group and a phenyl group having a hydrogen atom, a nitro group or an alkoxy group at the 4-position; or Is a phenyl group having a carboxyl group at the 2-position and 5-position or 3-position and 5-position to the zo group, and when m and 1 are 1, the bonding position is 3 or 4 and n 'is 1
- a ′ and D ′ each independently represent a phenyl group or a naphthyl group, and these groups are a halogen atom; a hydroxyl group; an amino group; a carboxyl group; a sulfo group; a nitro group; an alkyl group; An alkyl group substituted with a hydroxyl group, an alkoxy group, a sulfo group, or a carboxyl group; a hydroxyl group, an alkoxy group, a sulfo group, or a carboxyl group Alkoxy group; power Further substituted with a ruboxyl group or a sulfo group, or substituted with a phenyl group, an alkyl group or a sacyl group, and substituted with a lumino group; a benzothiazole group; a mesyl group; a sulphamoyl group. It is good! m and n represent 1 or 2)
- a tetrakisazoi ligated compound represented by or a salt thereof
- a ′ and D ′ in the formula (1 ′) are halogen atoms; hydroxyl groups; lower acylamino groups; carboxyl groups; sulfo groups; nitro groups; lower alkyl groups; A lower alkoxy group; may have a lower alkyl group or a sulfo group as a substituent on the benzene nucleus; a benzothiazole group; and a group consisting of a phosphono group, a mesyl group, and a sulfamoyl group are also selected.
- R1 and R2 each independently represent a hydrogen atom, a sulfo group or a carboxyl group, and R3 and R4 each independently represent a -toro group, a lower alkylsulfonyl group or a sulfamoyl group
- R3 and R4 each independently represent a -toro group, a lower alkylsulfonyl group or a sulfamoyl group
- R1 and R2 represent the same group selected from a hydrogen atom, a sulfo group or a carboxyl group, and R3 and R4 are the same groups selected from a -tro group, a mesyl group or a sulfamoyl group.
- R3 and R4 are the same groups selected from a -tro group, a mesyl group or a sulfamoyl group.
- the tetrakisazoi conjugate of the present invention is excellent in water solubility, it has good filterability with a membrane filter in the ink composition manufacturing process, and also has excellent storage liquid storage stability and ejection stability. ing.
- the ink composition of the present invention containing the tetrakisazoi conjugate has good storage stability without any crystal precipitation, change in physical properties, color change, and the like after long-term storage.
- the black ink for recording containing the tetrakisazoi compound of the present invention is used for ink jet recording and writing instruments, and has a higher recording density of a recorded image when recorded on plain paper and paper dedicated to inkjet.
- the image is excellent in ozone gas resistance, light resistance and moisture resistance, and has low color rendering.
- magenta, cyan and yellow dyes When used together with magenta, cyan and yellow dyes, full-color ink jet recording with excellent light fastness and water fastness is possible.
- the ink composition of the present invention is extremely useful as a black ink for inkjet recording.
- a and D each independently represent a phenyl group or a naphthyl group. Each of these may be further substituted or unsubstituted.
- substituents include a halogen atom such as chlorine and bromine; a hydroxyl group; an unsubstituted amino group; a carboxyl group; a sulfo group; a phosphono group; and a nitro group: methyl, ethyl, n-propyl, isopropyl, n-butyl, and isobutyl.
- Alkyl groups such as sec-butyl, tert-butyl
- a lower alkyl group such as a C1-C4 alkyl group
- an alkoxy group such as methoxy and ethoxy, preferably a lower alkoxy group such as a C1 C4 alkoxy group
- 2 hydroxyethoxy, 2-methoxyethoxy, 3 sulfopropoxy, 4 sulfo Alkoxy groups substituted with a hydroxy xyl group such as butoxy, an alkoxy group, a sulfo group or a carboxyl group, preferably lower alkoxy groups substituted with the above substituents, for example, substituted with the above substituents.
- the substituent, phenyl group, alkyl group and acyl group of the above-mentioned substituted amino group may further have a substituent.
- the substituent include a hydroxyl group, an alkoxy group, a carboxy group and a sulfo group.
- the substituted amino group include carboxymethylamino, biscarboxymethylamidoacetylamino, carboxypropylamido, ureido, and phenylamine-containing sulfo-fluoroamido-containing carboxyphenylamino-containing dicarboxyphenylamino.
- a and D are preferably a halogen atom; a carboxyl group; a sulfo group; a nitro group; an unsubstituted alkoxy group, preferably an unsubstituted lower alkoxy group, more preferably a methoxy group; a sulfoalkoxy group, preferably a sulfo lower alkoxy group; An acylamino group, preferably a lower amino group, more preferably an acetylamino group; a lower alkyl group and / or a sulfo group, or a benzothiazole group; a mesyl group or a sulfamoyl group.
- alkyl, alkoxy, acyl, alcohol, alcohol, etc. are not particularly limited in the number of carbon atoms, but are preferably 20 or less, more preferably It is 15 or less, more preferably 10 or less.
- the term “lower” is used to mean “C1-C6", preferably “C1-C4", unless otherwise specified.
- Preferable examples of the compound represented by the formula (1) of the present invention include, but are not particularly limited to, the following. In Table 1, the sulfo group, carboxyl group and phosphono group are represented in the form of free acid.
- preferred compounds include a compound represented by the formula (1 ′) or a compound represented by the formula (2).
- m ′ and n ′ each represent 1, the substitution position of the sulfo group is the 4-position and the 8-position, respectively, the bond position of the bond a is the 3-position, and the bond position of the bond b
- the compound at position 7 is a preferred compound as a recording dye, and more specifically, a compound in which A and D forces in Formula (2) are A 'and D', respectively (provided that A 'and D' Is the same as in equation (1 ').
- More preferred compounds are those wherein A and D in the formula (2) are substituted with a halogen atom; a hydroxyl group; a lower acylamino group; a carboxyl group; a sulfo group; a nitro group; a lower alkyl group; A lower alkoxy group, which may have a lower alkyl group or a sulfo group as a substituent on the benzene nucleus, a benzothiazole group, a phosphono group, a mesyl group, and a sulfamoyl group; And a compound which is substituted with two substituents and is a phenyl group, a phenyl group or a naphthyl group.
- a or D is, independently, 4-sulfamoylphenol, 4-mesylphenol, 2-carboxyl-4-sulfamoylphenol or 2-sulfo-4-troproyl. And when both are the same group, it is more preferable.
- the compounds represented by the formulas (1), (2) and (1 ′) exist in the form of a free acid or a salt thereof.
- examples of the salt include salts of inorganic or organic cations.
- specific examples of inorganic salts include alkali metal salts and ammonium salts.
- Preferred inorganic salts are lithium, sodium, potassium salts and ammonium salts, and organic cations.
- Examples of the salt include, but are not limited to, a salt of a compound represented by the following formula (3). [0014] [Formula 4]
- Z 4 each independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group or a hydroxyalkoxyalkyl group.
- alkyl groups include methyl, Echiru, n- propyl, isopropyl, n- butyl, I Sobuchiru, sec- butyl, tert- butyl and the like
- hydroxymethyl is an example of a hydroxyalkyl group
- a hydroxy- (C1-C4) alkyl group such as a hydroxy group, a hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, a 4-hydroxybutyl group, a 3-hydroxybutyl group, or a 2-hydroxybutyl group.
- hydroxyalkoxyalkyl group examples include a hydroxyethoxymethyl group, a 2-hydroxyethoxyethyl group, a 3-hydroxyethoxypropyl group, a 2-hydroxyethoxypropyl group, a 4-hydroxyethoxybutyl group, and a 3-hydroxyethoxybutyl group.
- Hydroxy (C1-C4) groups such as 2-hydroxyethoxybutyl group Kokishi - (C 1 ⁇ C4) alkyl group. Among these hydroxyethoxy one (C 1 ⁇ C4) alkyl groups are preferred.
- Z 4 particularly preferably respectively as the casting independently a hydrogen atom; a methyl group; hydroxymethyl group, hydroxyethyl E butyl group, 3-hydroxypropyl group, 2-hydroxypropyl, 4-hydroxybutyl group, 3-hydroxy Hydroxy- (C1-C4) alkyl groups such as butyl group and 2-hydroxybutyl group; hydroxyethoxymethyl group, 2-hydroxyethoxyshethyl group, 3-hydroxyethoxypropyl group, 2-hydroxyethoxypropyl group, 4-hydroxyethoxy group Examples thereof include a hydroxyethoxy (C1-C4) alkyl group such as a hydroxyethoxybutyl group, a 3-hydroxyethoxybutyl group, and a 2-hydroxyethoxybutyl group.
- C1-C4 alkyl group such as a hydroxyethoxybutyl group, a 3-hydroxyethoxybutyl group, and a 2-hydroxyethoxybutyl group.
- Equation (3) Specific examples of Z 4 shown in (Table 6).
- the compound represented by the formula (2) can be synthesized by any suitable method. (The structural formula of the compound in each step is expressed in the form of a free acid.) That is, a compound of the following formula (4) is reacted with a compound of the formula (5) under weak alkalinity,
- n has the same meaning as n in the formula (2). It is the same in the formula in the synthesis reaction described below.
- the phenyl group or the naphthyl group may each independently have a substituent.
- substituents include those described as the substituent for A or D in the formula (2). That is, a phenyl group or a naphthyl group in the above formula is represented by A or A in the formula (2). Used for convenience, instead of D, for simplicity.
- D for simplicity.
- the compound represented by the formula (11) or (12) is subjected to a diazoidation reaction and a coupling reaction with the compound represented by the formula (6) to obtain a compound represented by the following formula (21) or (22).
- Coupling of the compound of the formula (8) or (9) with the compound of the formula (10) is also carried out under conditions known per se. It is advantageous to work in aqueous or aqueous organic media, for example at temperatures of -5 to 30 ° C., preferably 10 to 25 ° C., and also at weakly acidic forces at alkaline pH values. It is preferably carried out at a neutral to alkaline pH value, for example pH 7 to: L1.
- the adjustment of the pH value is carried out by adding a base.
- the base include alkali metal hydroxides such as lithium hydroxide and sodium hydroxide, alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate, acetates such as sodium acetate, ammonia and organic compounds. Amines can be used.
- the compounds of formulas (8), (9) and (10) are used in approximately stoichiometric amounts.
- the diazotization of the compounds of the formulas (11) and (12) is also carried out in a manner known per se, for example in an organic acid medium at a temperature of, for example, ⁇ 5 to 30 ° C., preferably 0 to 20 ° C. It is carried out using a nitrite, for example an alkali metal nitrite such as sodium nitrite.
- the coupling of the compound of the formula (11) or (12) with the compound of the formula (7) is also carried out under conditions known per se. It is advantageous to work in an aqueous or aqueous organic medium, for example at a temperature of from 5 to 30 ° C., preferably from 0 to 10 ° C., and at a weakly acidic to slightly alkaline pH value.
- the pH value to neutral weak acid for example, carried out in P H3 ⁇ 7.
- a base is used to neutralize the acid generated as the reaction proceeds.
- the base include alkali metal hydroxides such as lithium hydroxide and sodium hydroxide, lithium carbonate, sodium carbonate and potassium carbonate.
- the compounds of formulas (11), (12) and (7) are used in approximately stoichiometric amounts.
- Coupling of the diazo compound of the compound of the formula (11) or (12) with the compound of the formula (21) or (22) is also carried out under conditions known per se. It is advantageous to carry out the reaction in aqueous or aqueous organic media, for example at a temperature of 5 to 30 ° C., preferably 10 to 25 ° C., and also with weakly acidic forces at alkaline pH values. Preferably neutral mosquito ⁇ Luo alkaline pH values, for example, P H7 ⁇ : carried out in L 1. The adjustment of the pH value is carried out by adding a base.
- hydroxyl Lithium alkali metal hydroxides such as sodium hydroxide, alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate, acetates such as sodium acetate, ammonium and organic amines can be used.
- alkali metal hydroxides such as sodium hydroxide
- alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate
- acetates such as sodium acetate
- ammonium and organic amines can be used as the base.
- the compounds of formulas (11), (12) and (21), (22) are used in approximately stoichiometric amounts.
- the tetrakisazoi conjugate represented by the formula (1), (1 ′) or (2) according to the present invention or a salt thereof is a cup.
- a compound or a salt thereof is simply referred to as a compound unless otherwise specified
- the acid type dye having a low salt content thus obtained can be neutralized with a desired inorganic or organic base in an aqueous medium to obtain a solution of the corresponding salt.
- inorganic bases include, for example, hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide, potassium hydroxide, hydroxide ammonium hydroxide, or lithium carbonate, sodium carbonate, carbonate
- examples thereof include carbonates of alkali metals such as potassium
- examples of the organic base include, but are not limited to, an organic amine represented by the above formula (3).
- solubility can be increased by converting a part or the whole to a lithium salt using lithium hydroxide, lithium carbonate or the like.
- the tetrakisazoi conjugate represented by the formula (1), (1 ') or (2) of the present invention, more preferably the tetrakisazoi conjugate represented by the formula (a) is a material having a cellulosic power. It is useful as a dye for dyeing materials having a carboxylic acid bond and other materials, and as a recording dye for printing and the like.
- the aqueous composition containing the tetrakisazoi conjugate can dye a material such as cellulose charcoal.
- a material such as cellulose charcoal.
- the preferred use of the compound of the present invention is an ink composition dissolved in a liquid medium.
- reaction solution containing the tetrakisazoi conjugate of the present invention can be used directly for producing a recording ink composition. Further, first, it is dried, for example, spray-dried to isolate it, or it is salted out with inorganic salts such as sodium chloride, potassium chloride, calcium chloride, sodium sulfate, etc., hydrochloric acid, sulfuric acid, nitric acid, etc. It is also possible to take out the tetrakisazoi conjugate of the present invention by acid praying with the above mineral acid or by performing salting out by combining the above salting out and aciding out, and then adding it to the ink composition. it can.
- inorganic salts such as sodium chloride, potassium chloride, calcium chloride, sodium sulfate, etc., hydrochloric acid, sulfuric acid, nitric acid, etc.
- the ink composition of the present invention mainly contains water containing 0.1 to 20% by mass, preferably 1 to 10% by mass, more preferably 2 to 8% by mass of the tetrakisazoi conjugate of the present invention. It is a composition used as a medium.
- the ink composition of the present invention may further contain, for example, 0 to 30% by mass of a water-soluble organic solvent and 0 to 5% by mass of an ink preparation agent. Therefore, the ink composition of the present invention is generally an aqueous ink composition containing water as the balance in addition to the tetrakisazolyid compound of the present invention, the water-soluble organic solvent, and the ink preparation agent.
- the pH of the ink composition is preferably pH 6 to 10, more preferably pH 7 to 10, from the viewpoint of improving storage stability.
- the surface tension of the ink composition is preferably 25 to 70 mNZm, more preferably 25 to 60 mNZm.
- the viscosity of the ink composition is preferably 30 mPa's or less, more preferably 20 mPa's or less.
- the tetrakisazoi conjugate of the present invention is dissolved in water or a water-soluble organic solvent (organic solvent or water containing an organic solvent miscible with water), and an ink preparation agent is added as necessary. It was done.
- a water-soluble organic solvent organic solvent or water containing an organic solvent miscible with water
- an ink preparation agent is added as necessary. It was done.
- the ink composition is used as an ink for an ink jet printer, it is preferable to use, as the tetrakisazoi conjugate, one having a low content of an inorganic substance such as a metal cation salt or a sulfate.
- the standard of the content is, for example, about 1% by mass or less (based on chromogen).
- a conventional method using a reverse osmosis membrane or a dried product or a wet cake of the azoi ligated compound of the present invention is stirred in a mixed solvent of alcohol such as methanol and water. Then, desalting may be performed by a method such as filtration and drying.
- ink preparation agents that can be used in the preparation of the ink composition of the present invention include, for example, antiseptics and fungicides, ⁇ adjusters, chelating reagents, antibacterial agents, water-soluble ultraviolet absorbers, water-soluble high molecular compounds, and dye dissolving agents. Agents, antioxidants, surfactants and the like.
- antiseptic / antifungal agent examples include organic sulfur-based, organic nitrogen-sulfur-based, organic halogen-based, noroarylsulfone-based, odopropargyl-based, haloalkylthio-based, benzothiazole-based, nitrile-based, pyridine-based, and 8-oxyquinoline.
- benzothiazole system isothiazoline system, dithiophenol system, pyridineoxide system, nitropropane system, organotin system, phenol system, quaternary ammonium salt system, triazine system, thiazine system, aldehyde system And adamantane compounds, dithiocarbamate compounds, brominated indanone compounds, benzyl bromacetate compounds, and inorganic salt compounds.
- organic halogen-based compound examples include sodium pentachlorophenol
- examples of the pyridineoxide-based compound include 2-pyridine Ginthiol-1-oxide sodium
- inorganic salt-based compounds include, for example, sodium acetic anhydride
- isothiazoline-based compounds for example, 1,2-benzisothiazolin-1-one, 2-n-octynole 1- 4-isothiazoline 1-3-one, 5 chloro-2 4-methinole 4 isothiazoline-3 on, 5 chloro-2-methinole 4 isothiazoline 1-3 on magnesium chloride, 5 chloro 1-2-methyl 4 isothiazoline 3 on calcium chloride, 2 Methyl 4 isothiazoline 3 on calcium chloride and the like.
- Other preservatives and fungicides include sodium sorbate and sodium benzoate. It is preferable to use 0.02 to 100% by mass of L in the ink composition.
- any substance can be used as long as it can control the pH of the ink composition within the range of, for example, 5 to L1, without adversely affecting the ink composition to be prepared.
- alkanolamines such as diethanolamine, triethanolamine and N-methyldiethanolamine
- hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and ammonium hydroxide.
- -Pharma ammonia
- alkali metal carbonates such as lithium carbonate, sodium carbonate, sodium hydrogen carbonate and potassium carbonate
- inorganic bases such as potassium acetate, sodium silicate and disodium phosphate.
- Examples of the chelating reagent include sodium ethylenediaminetetraacetate, sodium triacetate, sodium hydroxyethylethylenediaminetriacetate, sodium diethylenetriaminepentaacetate, and sodium peracylniacetate.
- Examples of the protective agent include acidic sulfite, sodium thiosulfate, ammonium thiodalcholate, diisopropylammonium-nitrite, pentaerythritol tetranitrate, dicyclohexylammonium-nitrite and the like. .
- water-soluble ultraviolet absorber examples include sulfonated benzophenone-based compounds, benzotriazole-based compounds, salicylic acid-based compounds, cinnamic acid-based compounds, and triazine-based compounds.
- water-soluble polymer compound examples include polyvinyl alcohol, cellulose derivatives, polyamine, polyimine and the like.
- dye dissolving agent examples include ⁇ -force prolatatam, ethylene carbonate, and urea.
- antioxidant for example, various organic and metal complex-based antifading agents can be used.
- organic anti-fading agent include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, a-lines, amines, indans, chromans, alkoxya-lines, heterocycles, and the like. Is mentioned.
- surfactant examples include known surfactants such as anionic, cationic, amphoteric, and nonionic surfactants.
- a-one surfactants include alkyl sulfonic acids, alkyl carboxylate salts, ⁇ -olefin sulfonic acid salts, polyoxyethylene alkyl ether acetate salts, dimethyl amino acids and salts thereof, and dimethyl methyl taurine salt.
- Cationic surfactants include 2-vinylpyridine derivatives and poly4-butylpyridine derivatives.
- amphoteric surfactants include betaine lauryl dimethylaminoacetate, 2-alkyl- ⁇ -carboxymethyl ⁇ hydroxyethyl imidazoly- ⁇ mbetaine, coconut oil fatty acid amidopropyl dimethylamino betaine, polyoctyl polyaminoethyl glycine and others There are imidazoline derivatives.
- non-ionic surfactant include polyoxyethylene nouryl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene dodecyl phenyl ether, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, and polyoxyethylene lauryl ether.
- Ethers such as oxyethylene alkyl ether, polyoxyethylene oleate, polyoxyethylene oleate, polyoxyethylene distearate, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquiolate, Polyesters such as polyxylene ethylene monolate, polyxixetylene lenstearate, 2,4,7,9-tetramethyl-5 decine 4,7-diol, 3,6 dimethyl-4-octyne 3,6 diol, 3,5 Dimethyl 1 Acetylene glycols such as hexin 3ol (for example, Surfinol 104, 105, 82, 465, and Olfine STG, manufactured by Nissin Chemical Co., Ltd.); These ink preparations are used alone or in combination.
- hexin 3ol for example, Surfinol 104, 105, 82, 465, and Olfine STG, manufactured by Nissin Chemical Co., Ltd.
- the ink composition of the present invention is obtained by mixing and stirring the above components in an arbitrary order.
- the obtained ink composition may be filtered with a membrane filter or the like to remove impurities.
- other pigments having various hues may be mixed.
- a dye of yellow, magenta, cyan or other hues can be used in addition to the tetrakisazoi conjugate of the present invention.
- the ink composition of the present invention is suitable for aqueous inks for writing, aqueous printing inks, information recording inks, and the like that can be used in various fields, and ink jet inks containing the ink compositions. It is particularly preferable to use it as an ink. Therefore, the ink for ink jet of the present invention is characterized by containing the ink composition of the present invention, and the ink for ink jet of the present invention is suitably used in the ink jet recording method of the present invention described later.
- the inkjet recording method of the present invention is characterized in that recording is performed using an inkjet ink containing the ink composition.
- recording is performed on an image receiving material using an ink-jet ink containing the above-mentioned ink composition, but there is no particular limitation on an ink nozzle or the like used at that time. It can be selected as appropriate.
- the image receiving material is not particularly limited, and known recording materials, for example, plain paper, resin-coated paper, inkjet-only paper, film, electrophotographic common paper, fabric, glass, metal, ceramic, and the like Is mentioned.
- ink jet-only paper for example, use of the following recording papers and recording films referred to as ink jet-only paper, ink jet-only glossy paper, ink jet-only film, etc. But especially preferred.
- the recording paper and the recording film are each formed by laminating an image receiving layer on a support. Other layers such as a knock coat layer may be laminated. Each layer including the image receiving layer is
- the support is made of chemical pulp such as LBKP and NBKP, mechanical pulp such as GP, PGW, RMP, TMP, CTMP, CMP and CGP, waste paper pulp such as DIP and the like.
- chemical pulp such as LBKP and NBKP
- mechanical pulp such as GP, PGW, RMP, TMP, CTMP, CMP and CGP
- waste paper pulp such as DIP and the like.
- pigments, kneaders, sizing agents, fixing agents, cationic agents, paper strength enhancers, etc. are added and mixed, and those manufactured by various apparatuses such as fourdrinier paper machines and circular net paper machines can be used.
- synthetic paper, plastic film sheet and the like may be used.
- the thickness of the support is preferably about 10 to 250 ⁇ m, and the basis weight is preferably 10 to 250 gZm 2 .
- the image receiving layer may be provided directly on the support, or the image receiving layer may be provided on the back coat layer.
- a size press or anchor using starch, polybutyl alcohol or the like may be used.
- the image receiving layer and the back coat layer may be provided.
- the support may be subjected to a flattening process using a calendar device such as a machine calendar, a TG calendar, or a soft calendar.
- paper and plastic films laminated on both sides with polyolefin eg, polyethylene, polystyrene, polyethylene terephthalate, polybutene, and copolymers thereof
- polyolefin eg, polyethylene, polystyrene, polyethylene terephthalate, polybutene, and copolymers thereof
- the image receiving layer may contain a pigment, an aqueous binder, a mordant, a waterproofing agent, a lightfastness improving agent, a surfactant, and other additives.
- a white pigment is preferred.
- the white pigment include calcium carbonate, kaolin, talc, clay, diatomaceous earth, synthetic amorphous silica, aluminum silicate, magnesium silicate, calcium silicate, and the like.
- Inorganic white pigments such as aluminum hydroxide, alumina, lithopone, zeolite, barium sulfate, calcium sulfate, titanium dioxide, zinc sulfide, zinc carbonate, etc .; organic facial pigments such as styrene pigment, acrylic pigment, urea resin, melamine resin, etc. And the like.
- porous inorganic pigments are preferred.
- aqueous binder examples include polyvinyl alcohol, silanol-modified polyvinyl alcohol, starch, cationized starch, casein, gelatin, and carboxyme.
- Water-soluble polymers such as tilcellulose, hydroxyethylcellulose, polyvinylpyrrolidone, polyanolexylene oxide, and polyalkylene oxide derivatives; and water-dispersible polymers such as styrene butadiene latex and acrylemulsion.
- These aqueous binders may be used alone or in combination of two or more.
- mordant a polymer mordant is preferably used.
- the water-proofing agent is effective for making the image water-resistant, and a preferred example thereof is a cationic resin.
- a cationic resin examples include polyamide polyamine epichlorohydrin, polyethyleneimine, polyamine sulfone, dimethyldiarylammonium chloride polymer, cationic polyacrylamide, and colloidal silica.
- Examples of the light resistance improver include zinc sulfate, zinc oxide, hindered amine-based antioxidants, benzophenone-based and benzotriazole-based ultraviolet absorbers, and the like.
- the surfactant functions as a coating aid, a release improver, a slipperiness improver, or an antistatic agent.
- An organic fluoro compound may be used instead of the surfactant!
- examples of the organic fluoro compound include a fluorine-based surfactant, an oily fluorine-based compound (eg, fluorine oil) and a solid fluorine compound resin (eg, tetrafluoroethylene resin).
- Examples of the other additives include a pigment dispersant, a thickener, an antifoaming agent, a dye, a fluorescent whitening agent, a preservative, a PH adjuster, a matting agent, and a hardening agent.
- the back coat layer may contain a white pigment, an aqueous binder, and other components.
- Examples of the white pigment include light calcium carbonate, heavy calcium carbonate, lime ore, talc, calcium sulfate, barium sulfate, titanium dioxide, zinc oxide, zinc sulfide, zinc carbonate, satin white, and aluminum silicate. , Diatomaceous earth, calcium silicate, magnesium silicate, synthetic amorphous silica, colloidal silica, colloidal alumina, pseudoboehmite, aluminum hydroxide, alumina, lithobon, zeolite, hydrohaloisite, magnesium carbonate, magnesium hydroxide hydroxide, etc.
- aqueous binder examples include styrene Z maleate copolymer, styrene Z acrylate copolymer, polyvinyl alcohol, silanol-modified polyvinyl alcohol, starch, cationized starch, casein, gelatin, carboxymethyl cellulose, Examples thereof include water-soluble polymers such as hydroxyxethyl cellulose and polyvinylpyrrolidone, and water-dispersible polymers such as styrene-butadiene latex and acryl emulsion.
- Examples of the other components include an antifoaming agent, an antifoaming agent, a dye, a fluorescent whitening agent, a preservative, and a waterproofing agent.
- a polymer latex may be added to the constituent layers (including the back coat layer) of the recording paper and recording film.
- the polymer latex is used for the purpose of improving film physical properties such as dimensional stability, curl prevention, adhesion prevention, and film crack prevention.
- a polymer latex having a low glass transition temperature 40 ° C. or less
- a polymer latex having a high glass transition temperature is added to the back coat layer, curling can be prevented.
- the inkjet recording method of the present invention is not particularly limited, and is a known method, for example, a charge control method for discharging ink using electrostatic attraction, a drop-on-demand method using vibration pressure of a piezo element.
- Pressure pulse method Acoustic ink jet method in which an electric signal is converted into an acoustic beam, and the ink is radiated to the ink and the ink is ejected using the radiation pressure.
- Thermal which heats the ink to form bubbles and uses the generated pressure Any of an inkjet (bubble jet (registered trademark)) method and the like may be used.
- the inkjet recording method includes a method of ejecting a large number of low-density inks called photo inks in a small volume, a method of improving image quality by using a plurality of inks having substantially the same hue and different densities, and a method of colorless transparency. Includes ink-based methods.
- the tetrakisazoi conjugate of the present invention is excellent in water solubility, and the ink composition of the present invention containing a tetrakisazo compound has storage stability that eliminates crystal precipitation, change in physical properties, color change and the like after long-term storage. Good.
- the black ink liquid for recording containing the tetrakisazoi conjugate of the present invention is used for ink jet recording and for writing implements, and can be used for plain paper and ink.
- the hue of the recorded image when recorded on jet-only paper is -Eutral, black with high print density, and is excellent in ozone gas resistance, light resistance, moisture resistance and color rendering properties.
- the pH value of the reaction solution was maintained at 8.5 to 9.5 with sodium carbonate.
- the pH value was further adjusted to 8.5 to 9.5 with sodium carbonate, and the mixture was stirred at a temperature of 10 to 15 ° C for 2 hours to complete the coupling reaction, and then sodium chloride was added. Salting out was carried out, followed by filtration, and the obtained wet cake was dried to obtain 36.3 parts of a monoazo conjugate of the following formula (23).
- (Fifth step) Disperse 20.3 parts of 2-amino-5-methoxybenzenesulfonic acid in 200 parts of water, add 31.3 parts of 35% hydrochloric acid, and cool to 5 to 10 ° C. Then, at the same temperature, 18.1 parts of a 40% aqueous sodium nitrite solution was added and kneaded to diazoi. Next, the diazo suspension thus obtained was added to the reaction solution containing the compound of the formula (27) obtained in the fourth step at 15 to 20 ° C., and then the ⁇ value was gradually reduced to 7 with sodium carbonate. Neutralized to 5-9.0.
- reaction solution containing the above disazoy conjugate was heated to 70 to 75 ° C, and then treated with sodium hydroxide for 2 hours while maintaining the pH value at 10.0 to L: 1.0. Afterwards, pH with hydrochloric acid The mixture was neutralized to a value of 7.0, salted out by adding sodium salt, and the precipitated precipitate was filtered and dried to obtain 73.4 parts of a diazoi compound of the following formula (32).
- Example 2 was repeated except that 29.7 parts of 2-amino-5-methoxybenzenesulfonic acid were used instead of 38.4 parts of 2-amino-5-trobezenesulfonic acid in the second step of Example 3.
- a black pigment represented by the following formula (34) (compound No. 19 in Table 2: Na salt) was obtained.
- the maximum absorption wavelength of this dye in water was 612 nm, and the solubility test in water (ammonia alkali) with a filter paper spot was 100 gZl or more.
- Example 3 In the second step of Example 3, a method similar to that of Example 3 was used except that 29.0 parts of 5-aminoisophthalic acid was used instead of 38.4 parts of 2-amino-5-trobezenesulfonic acid. 75.0 parts of a black pigment of the formula (35) (compound No. 17 in Table 2: Na salt) were obtained. The maximum absorption wavelength of this dye in water was 604 nm, and the solubility test in water (ammonia alkali) using a filter paper spot was 100gZl or more.
- a black pigment of the formula (35) compound No. 17 in Table 2: Na salt
- the reaction solution containing the above disazoi conjugate was heated to 70 to 75 ° C., and the pH was maintained at 10.0 to: L 1.0 with 25% sodium hydroxide. After treating for an hour, the mixture was neutralized with 35% hydrochloric acid. Next, the salted-out sodium salt was added to carry out salting-out, and the precipitated cake was filtered and dried to obtain 37.0 parts of a disazoi-ligated product of the following formula (39).
- the diazo suspension thus obtained is added to a solution of 37.0 parts of the compound of the formula (39) in 1000 parts of water at 15 to 20 ° C, and then gradually added with sodium carbonate.
- the pH value was neutralized to 6.0-7.0.
- the mixture was further stirred at 15 to 20 ° C and pH 7.0 to 8.0 for 3 hours to complete the coupling reaction, thereby obtaining a reaction solution containing the compound of the following formula (40).
- sodium chloride was added thereto for salting out, followed by filtration to obtain 300 parts of a wet cake of a tetrakisazoi ligated product of the formula (40).
- the ⁇ value of the reaction solution was maintained at 8.5 to 9.5 with sodium carbonate. After completion of the dropwise addition, the mixture was further stirred for 3 hours at a ⁇ value of 8.5 to 9.5 and a temperature of 10 to 15 ° C to complete the coupling reaction.After that, sodium chloride was added for salting out, followed by filtration. The obtained wet cake was dried to obtain 36.3 parts of a monoazo conjugate of the following formula (41).
- the diazo suspension thus obtained was dropped into the alkaline aqueous solution of the compound of the formula (42) obtained in the second step at 15 to 20 ° C.
- the pH value of the solution was maintained at 8.5 to 9.5 with sodium carbonate.
- the mixture was further stirred at 15 to 30 ° C. for 3 hours at pH 8.5 to 9.5 to complete the coupling reaction, thereby obtaining a reaction solution containing the compound of the following formula (44).
- the insoluble matter was removed by filtration, sodium salt was added, salting out was performed, and filtration was performed.
- the total amount of the obtained cake was dissolved in 500 parts of water, crystallized with 500 parts of methanol added to methanol, filtered to obtain a desalted wet cake, and then dried to obtain the formula (44) of the present invention (44) 77.8 parts of a black pigment of the compound No. 21 in Table 3: Na salt) were obtained.
- the maximum absorption wavelength ( ⁇ max) of this dye in water was 620 nm, and the solubility test in water (ammonia alkali) using a filter paper spot was 100 gZl or more.
- An ink composition of the present invention was prepared by mixing the following components, and filtered through a 0.45 nm membrane filter to obtain an ink composition for inkjet.
- the black dyes obtained in the above Examples are the compounds of Formula (28) in Example 10, the compounds of Formula (30) in Example 11, and the compounds of Formula (33) in Example 12
- Example 13 shows the compound of the formula (34)
- Example 14 shows the compound of the formula (35)
- Example 15 shows the compound of the formula (36).
- Example 16 shows a compound of the formula (40)
- Example 17 shows a compound of the formula (44)
- Example 18 shows a compound of the formula (49).
- the pH during ink preparation was adjusted to 8 to 10 with aqueous ammonia.
- the obtained ink composition of the present invention did not cause sedimentation and separation during storage, and showed no change in physical properties even after long-term storage.
- Ink jet recording was performed on three types of paper, PM photo paper (glossy) KA420PSK). At the time of printing, an image pattern was formed such that a reflection density of several gradations was obtained, and a halftone black print was obtained. Since the gray scale mode is used for printing, yellow, cyan, and magenta recording liquids other than the black recording liquid are not used in this light-colored portion. Among the test methods described below, in the hue density evaluation, which is an item evaluated using a colorimeter, the portion having the highest D value was used when measuring the reflection density D value of the printed matter.
- the hue, the hue density, the hue change after the light fastness test, the hue change after the ozone gas fastness test, the degree of bleeding by the moisture fastness test, and the color rendering 6 points were evaluated.
- the ozone gas resistance test and the moisture resistance test were carried out only for the special light paper A and B. The results are shown in (Table 8). The test method is shown below.
- the hue of the recorded image was measured using a Gretag Macbeth SpectroEye (manufactured by GRETAG) to calculate the hue density D value. Hue evaluation was visually determined. Hue density was determined by D value. The criteria are shown below. Hue evaluation
- Each printed sample was left for 1 hour at an ozone concentration of 12 ppm, a humidity of 60% RH and a temperature of 24 ° C. using an ozone weather meter (manufactured by Suga Test Instruments Co., Ltd.). After the test, the color was measured in the same manner as above, and the color difference ( ⁇ ) before and after the test and the residual ratio of the hue density were measured. The judgment was made based on the following criteria.
- the degree of discoloration when viewed under tungsten light was visually determined based on the hue under a standard light source.
- ink compositions having the same composition as in Examples 10 to 18 were prepared for C.I. Food Black 2 (the following formula (50)), an azo dye used as a water-soluble inkjet black dye.
- C.I. Food Black 2 the following formula (50)
- an azo dye used as a water-soluble inkjet black dye.
- Tables 7-1 and 8-2 The results of the hue evaluation, hue density evaluation, light resistance evaluation, ozone gas resistance evaluation, moisture resistance evaluation, and color rendering evaluation of the obtained recorded image are shown in Tables 7-1 and 8-2.
- the ink composition containing the tetrakisazoy compound of the present invention has a hue, ozone gas resistance, light resistance, and moisture resistance as compared with the conventional black dye (comparative example).
- the properties required for ink-jet recording, such as printing properties and color rendering properties, are generally excellent.
- the ink composition containing the tetrakisazoi conjugate of the present invention is used as an ink liquid for ink jet recording and writing implements.
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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 (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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JP2006513017A JPWO2005108502A1 (ja) | 2004-05-10 | 2005-05-09 | テトラキスアゾ化合物、記録用色素、インク組成物及び着色体 |
US11/579,289 US20070227388A1 (en) | 2004-05-10 | 2005-05-09 | Tetrakisazo Compound, Coloring Matter for Recording, Ink Composition and Colored Article |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2004-139412 | 2004-05-10 | ||
JP2004139412 | 2004-05-10 |
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WO2005108502A1 true WO2005108502A1 (ja) | 2005-11-17 |
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PCT/JP2005/008438 WO2005108502A1 (ja) | 2004-05-10 | 2005-05-09 | テトラキスアゾ化合物、記録用色素、インク組成物及び着色体 |
Country Status (4)
Country | Link |
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US (1) | US20070227388A1 (ja) |
JP (1) | JPWO2005108502A1 (ja) |
KR (1) | KR20070005009A (ja) |
WO (1) | WO2005108502A1 (ja) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006076908A (ja) * | 2004-09-08 | 2006-03-23 | Nippon Kayaku Co Ltd | ポリアゾ化合物の製造方法 |
JP2012087301A (ja) * | 2010-10-16 | 2012-05-10 | Ilford Imaging Switzerland Gmbh | 黒色ジスアゾ色素、該ジスアゾ色素の調製および使用方法 |
WO2014156851A1 (ja) * | 2013-03-26 | 2014-10-02 | 日本化薬株式会社 | 黒色用テトラキスアゾ化合物、それを含む染料組成物及びその使用 |
EP2924082A1 (en) | 2014-03-24 | 2015-09-30 | Canon Kabushiki Kaisha | Ink, ink cartridge, and ink jet recording method |
WO2020137691A1 (ja) * | 2018-12-27 | 2020-07-02 | 日本化薬株式会社 | アゾ化合物又はその塩、並びにこれを含有する染料系偏光膜及び染料系偏光板 |
WO2020137705A1 (ja) * | 2018-12-27 | 2020-07-02 | 日本化薬株式会社 | アゾ化合物又はその塩、並びにこれを含有する染料系偏光膜及び染料系偏光板 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004078860A1 (ja) * | 2003-03-05 | 2004-09-16 | Nippon Kayaku Kabushiki Kaisha | 水性黒色インク組成物及び着色体 |
CN116731531A (zh) * | 2023-06-28 | 2023-09-12 | 水木聚力接枝纺织新技术(深圳)有限公司 | 一种水溶性双丙烯酰基γ酸染料及其合成方法和用途 |
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JPS557869A (en) * | 1978-07-04 | 1980-01-21 | Canon Inc | Liquid recording medium |
JPH07138492A (ja) * | 1993-09-27 | 1995-05-30 | Taoka Chem Co Ltd | テトラキスアゾ化合物及びその用途 |
JPH08302220A (ja) * | 1995-04-28 | 1996-11-19 | Taoka Chem Co Ltd | テトラキスアゾ化合物及びそれを含む記録液 |
WO2004078860A1 (ja) * | 2003-03-05 | 2004-09-16 | Nippon Kayaku Kabushiki Kaisha | 水性黒色インク組成物及び着色体 |
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EP0645436A1 (en) * | 1993-09-27 | 1995-03-29 | Sumitomo Chemical Company, Limited | Tetrakisazo compound and ink containing the compound |
JP4517174B2 (ja) * | 2003-03-05 | 2010-08-04 | 日本化薬株式会社 | テトラキスアゾ化合物、水性インク組成物及び着色体 |
JP3885086B2 (ja) * | 2004-07-02 | 2007-02-21 | キヤノン株式会社 | インクジェット用ブラックインク、インクセット、インクジェット記録方法、インクカートリッジ、記録ユニット及びインクジェット記録装置 |
-
2005
- 2005-05-09 WO PCT/JP2005/008438 patent/WO2005108502A1/ja active Application Filing
- 2005-05-09 US US11/579,289 patent/US20070227388A1/en not_active Abandoned
- 2005-05-09 JP JP2006513017A patent/JPWO2005108502A1/ja active Pending
- 2005-05-09 KR KR1020067025022A patent/KR20070005009A/ko not_active Application Discontinuation
Patent Citations (4)
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JPS557869A (en) * | 1978-07-04 | 1980-01-21 | Canon Inc | Liquid recording medium |
JPH07138492A (ja) * | 1993-09-27 | 1995-05-30 | Taoka Chem Co Ltd | テトラキスアゾ化合物及びその用途 |
JPH08302220A (ja) * | 1995-04-28 | 1996-11-19 | Taoka Chem Co Ltd | テトラキスアゾ化合物及びそれを含む記録液 |
WO2004078860A1 (ja) * | 2003-03-05 | 2004-09-16 | Nippon Kayaku Kabushiki Kaisha | 水性黒色インク組成物及び着色体 |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006076908A (ja) * | 2004-09-08 | 2006-03-23 | Nippon Kayaku Co Ltd | ポリアゾ化合物の製造方法 |
JP4641768B2 (ja) * | 2004-09-08 | 2011-03-02 | 日本化薬株式会社 | ポリアゾ化合物の製造方法 |
JP2012087301A (ja) * | 2010-10-16 | 2012-05-10 | Ilford Imaging Switzerland Gmbh | 黒色ジスアゾ色素、該ジスアゾ色素の調製および使用方法 |
WO2014156851A1 (ja) * | 2013-03-26 | 2014-10-02 | 日本化薬株式会社 | 黒色用テトラキスアゾ化合物、それを含む染料組成物及びその使用 |
EP2924082A1 (en) | 2014-03-24 | 2015-09-30 | Canon Kabushiki Kaisha | Ink, ink cartridge, and ink jet recording method |
US9453138B2 (en) | 2014-03-24 | 2016-09-27 | Canon Kabushiki Kaisha | Ink, ink cartridge, and ink jet recording method |
WO2020137691A1 (ja) * | 2018-12-27 | 2020-07-02 | 日本化薬株式会社 | アゾ化合物又はその塩、並びにこれを含有する染料系偏光膜及び染料系偏光板 |
WO2020137705A1 (ja) * | 2018-12-27 | 2020-07-02 | 日本化薬株式会社 | アゾ化合物又はその塩、並びにこれを含有する染料系偏光膜及び染料系偏光板 |
JPWO2020137691A1 (ja) * | 2018-12-27 | 2021-11-11 | 日本化薬株式会社 | アゾ化合物又はその塩、並びにこれを含有する染料系偏光膜及び染料系偏光板 |
JPWO2020137705A1 (ja) * | 2018-12-27 | 2021-11-11 | 日本化薬株式会社 | アゾ化合物又はその塩、並びにこれを含有する染料系偏光膜及び染料系偏光板 |
JP7507695B2 (ja) | 2018-12-27 | 2024-06-28 | 日本化薬株式会社 | アゾ化合物又はその塩、並びにこれを含有する染料系偏光膜及び染料系偏光板 |
JP7507694B2 (ja) | 2018-12-27 | 2024-06-28 | 日本化薬株式会社 | アゾ化合物又はその塩、並びにこれを含有する染料系偏光膜及び染料系偏光板 |
Also Published As
Publication number | Publication date |
---|---|
JPWO2005108502A1 (ja) | 2008-03-21 |
US20070227388A1 (en) | 2007-10-04 |
KR20070005009A (ko) | 2007-01-09 |
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