WO2016021730A1 - Compose azoique hydrosoluble ou sel de celui-ci, composition d'encre et corps colore - Google Patents

Compose azoique hydrosoluble ou sel de celui-ci, composition d'encre et corps colore Download PDF

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Publication number
WO2016021730A1
WO2016021730A1 PCT/JP2015/072586 JP2015072586W WO2016021730A1 WO 2016021730 A1 WO2016021730 A1 WO 2016021730A1 JP 2015072586 W JP2015072586 W JP 2015072586W WO 2016021730 A1 WO2016021730 A1 WO 2016021730A1
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Prior art keywords
group
salt
formula
ink
azo compound
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PCT/JP2015/072586
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English (en)
Japanese (ja)
Inventor
真也 永塚
梅田　真理子
順哉 柵木
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日本化薬株式会社
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Priority to JP2016540766A priority Critical patent/JP6592443B2/ja
Publication of WO2016021730A1 publication Critical patent/WO2016021730A1/fr

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Classifications

    • 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
    • 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
    • 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
    • B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
    • 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
    • B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
    • B41M5/52—Macromolecular coatings
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
    • 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
    • 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 water-soluble azo compound or a salt thereof, an ink composition containing the same, and a colored body colored with these.
  • ink ejection methods have been developed as recording methods using an ink jet printer, which is one of the representative methods. These all generate ink droplets and attach them to various recording materials (paper, film, fabric, etc.) for recording. In this method, since the recording head and the recording material are not in direct contact with each other, no noise is generated and the method is quiet. In addition, since it has the characteristics that it is easy to downsize, speed up, and colorize, it has been rapidly spreading in recent years and is expected to grow greatly in the future. Conventionally, inks such as fountain pens and felt pens, and inks for ink-jet recording have been used in which water-soluble pigments (dyes) are dissolved in an aqueous medium.
  • inks such as fountain pens and felt pens, and inks for ink-jet recording have been used in which water-soluble pigments (dyes) are dissolved in an aqueous medium.
  • a water-soluble organic solvent is added to these water-based inks in order to prevent clogging of ink at a pen tip or an ink discharge nozzle.
  • These inks give a recorded image of sufficient density, do not cause clogging of the pen tip and nozzles, have good drying properties on the recording material, have little bleeding, and have excellent storage stability. Such performance is required.
  • Ink jet nozzle clogging occurs when the water in the ink evaporates in the vicinity of the nozzle before other solvents and additives, and the pigment solidifies and precipitates when the composition state is low in water and high in solvents and additives.
  • the very important required performances is that solids are not easily deposited even when the moisture content in the ink is low. For this reason, high solubility in solvents and additives is one of the properties required for pigments.
  • a method for eliminating nozzle clogging a method using a dye having a high printing density is known. By using a pigment having a high printing density, the pigment content in the ink can be reduced while maintaining the conventional printing density. This not only makes it difficult to precipitate the dye, but is also advantageous in terms of cost, and development of a dye having a high printing density is desired.
  • the color area that can be expressed in a single color or mixed color becomes narrow, and the range of the color area that is desired to be expressed may be insufficient. For this reason, development of highly saturated pigments and inks containing them is desired.
  • the ink performance is required to be stable for long-term storage, high in recorded image density, and excellent in fastness such as water resistance, moisture resistance, light resistance and gas resistance. It is done.
  • the gas resistance means that a gas having an oxidizing action (also referred to as an oxidizing gas) existing in the air reacts with a dye (dye) of a recorded image on the recording material or in the recording material to record.
  • ozone gas is considered to be a main causative substance that promotes the discoloration and fading phenomenon of ink jet recorded images. Since this discoloration phenomenon is characteristic of ink jet recorded images, improvement of ozone gas resistance is an important technical problem in this field.
  • inkjet printers have the advantage that the type of recording paper is not limited, and the price of the printer itself is low, and the spread is particularly widespread in small to medium-sized office environments such as small offices and home offices (SOHO).
  • SOHO small offices and home offices
  • pigment ink does not dissolve in water-based ink, it does not enter a solution state, but is a dispersed ink. Therefore, when this is used for ink jet recording, there are problems with the stability of the ink itself and the nozzles of the recording head. Problems such as clogging occur.
  • pigment ink when pigment ink is used, there is often a problem in abrasion resistance. In the case of a dye ink, such a problem is considered to be relatively difficult to occur.
  • the moisture resistance is extremely inferior to that of a pigment ink, and an improvement to the problem is strongly desired.
  • dye ink tends to cause a problem that a dye attached to the surface of plain paper by ink jet recording penetrates more quickly toward the back side of the paper, resulting in a decrease in color density.
  • the ink receiving layer As one method for obtaining a photographic image-recorded inkjet image, there is a method of providing an ink receiving layer on the surface of a recording material.
  • the ink receiving layer provided for such a purpose often contains a porous white inorganic substance in order to speed up drying of the ink and to reduce bleeding of the pigment with high image quality.
  • the color fading due to the ozone gas is noticeable.
  • the above-mentioned color change of recorded images due to oxidizing gas is regarded as a problem. .
  • yellow dyes Compared to the other three primary colors, magenta and cyan, yellow dyes have been proposed that have good resistance to oxidizing gas as well as light resistance. However, a yellow pigment and yellow ink for ink-jet recording that sufficiently satisfy the high sharpness and various fastnesses required by the market have not been obtained yet.
  • Patent Documents 1 to 3 include C.I. I. An example in which (color index) direct yellow 132 is used for inkjet is disclosed.
  • Patent Document 4 discloses an example in which a yellow pigment that can be produced by the method disclosed in Example 1 of Patent Document 5 is used for inkjet.
  • JP-A-11-70729 Japanese Patent No. 3346755 Japanese Patent No. 4100800 International Publication No. 2011/122426 International Publication No. 2009/154142
  • the present invention is a water-soluble yellow dye (compound) having high solubility in water, high color development (printing density) of recorded images, excellent chroma and light resistance, and various recordings containing the same, particularly
  • An object is to provide a yellow ink composition for inkjet recording.
  • A represents a water-soluble substituent.
  • the water-soluble substituent is highly hydrophilic, that is, the present invention 0)
  • Thio group which may be substituted with one or more substituents selected from hydroxy group, carboxy group, carbamoyl group and sulfo group
  • C1-C4 alkylamino group hydroxy group, carb
  • Y represents 0 or 1
  • z represents 0 or 1
  • x represents an integer of 2 to 4
  • a and b represent the substitution positions of A 1 , A 2 or R.
  • x is 3 and the azo compound or salt thereof according to 0) or 1) above, 3)
  • T is a sulfo group or a carboxy group, and the azo compound or salt thereof according to any one of 0) to 4), 6)
  • R is a chlorine atom or a methoxy group
  • 16) (A) The azo compound or a salt thereof according to any one of 0) to 9) above, (B) an ink composition containing the azo compound or a salt thereof according to any one of 0) to 9), or (C) A colored body colored with any of the ink composition containing the azo compound or salt thereof according to any one of 0) to 9) and a water-soluble organic solvent, 17) A colored body colored by the inkjet recording method according to any one of 13) to 15 above, 18) An ink jet printer loaded with a container containing the ink composition according to 10) or 11) above; 19) A method for producing the azo compound or salt thereof according to any one of 0) to 0-4), A method comprising condensing a compound represented by the following formula (5) and a halogenated formate.
  • the azo compound of the present invention represented by the above formula (1) or formula (1a) or a salt thereof is highly soluble in water and may be said to be a water-soluble azo compound or a salt thereof. It has a feature of good filterability in the process of producing the ink composition of the present invention containing a salt, for example, filterability for a membrane filter.
  • an image recorded by the ink composition of the present invention containing the compound of the present invention is excellent in printing density, saturation and light resistance as compared with those using a conventional compound.
  • the azo compound of the present invention represented by the formula (1) or the formula (1a) or a salt thereof, and the ink composition containing the same are used for various recording inks, particularly for ink jet recording. Very useful.
  • the present invention will be described in detail.
  • the azo compound of the present invention represented by the above formula (1) or a salt thereof is a water-soluble yellow dye.
  • acidic functional groups such as sulfo groups and carboxy groups are represented in the form of free acids.
  • the present invention includes both the azo compound represented by the formula (1) or a salt of the compound, but it is complicated to always write both of them together as “a compound or a salt thereof”. . Therefore, unless otherwise specified, for convenience, both the “(azo) compound of the present invention or a salt thereof” and the “azo compound of the present invention”, that is, “the azo compound of the present invention” or “the present invention” are included. The following is simply described as “the compound of the invention”. The same applies to the azo compound represented by the formula (1a) or a salt thereof.
  • x represents an integer of 2 to 4, preferably 3.
  • A is substituted at the position of a or b, a is more preferred, R is substituted at the position of a or b, and b is more preferred.
  • R is substituted at position a
  • R is substituted at position b
  • R is substituted at position a.
  • R is a hydrogen atom described later is also referred to as “substituted” for the sake of convenience in this specification.
  • A represents a water-soluble substituent.
  • the water-soluble substituent means a highly hydrophilic substituent, and is a sulfo group, a carboxy group, a phospho group, a C1-C4 alkyl group (substituted with one or more sulfo groups, a carboxy group or a phospho group) ), C1-C4 alkoxy group (substituted with one or more sulfo group, carboxy group or phospho group), C1-C4 sulfoalkyl group (substituted with one or more sulfo group, carboxy group or phospho group) C1-C4 alkylthio group (substituted with one or more sulfo group, carboxy group or phospho group), C1-C4 alkylamino group (substituted with one or more sulfo group, carboxy group or phospho group), etc.
  • a sulfo group a carboxy
  • T represents a water-soluble substituent.
  • the water-soluble substituent means a highly hydrophilic substituent, and is a sulfo group, a carboxy group, a phospho group, a C1-C4 alkyl group (substituted with one or more sulfo groups, a carboxy group or a phospho group) ), C1-C4 alkoxy group (substituted with one or more sulfo group, carboxy group or phospho group), C1-C4 sulfoalkyl group (substituted with one or more sulfo group, carboxy group or phospho group) C1-C4 alkylthio group (substituted with one or more sulfo group, carboxy group or phospho group), C1-C4 alkylamino group (substituted with one or more sulfo group, carboxy group or phospho group), etc.
  • a sulfo group a carboxy
  • Q and R are each independently a hydrogen atom, halogen atom, carboxy group, carbamoyl group, sulfo group, sulfamoyl group, hydroxy group, amino group, cyano group, phospho group, nitro group, acyl group, C1-C4 alkyl group ( A C1-C4 alkoxy group (which may be substituted with one or more substituents selected from a hydroxy group, a carboxy group, a carbamoyl group, and a sulfo group), a hydroxy group, a carboxy group, a carbamoyl group, and a sulfo group 1 or 2 or more substituents selected from a C1-C4 sulfoalkyl group (hydroxy group, carboxy group, carbamoyl group, and sulfo group).
  • C1-C4 alkylthio group hydroxy group, carboxy group, carbamoyl group, And optionally substituted with one or more substituents selected from a sulfo group
  • C1-C4 alkylamino group hydroxy group, carboxy group, carbamoyl group, and one or more selected from a sulfo group
  • Q is preferably a halogen atom, more preferably a chlorine atom.
  • R is a halogen atom, a hydroxy group, an amino group, a C1-C4 alkoxy group (which may be substituted with one or more substituents selected from a hydroxy group, a carboxy group, a carbamoyl group and a sulfo group), C1- A C4 alkylthio group (which may be substituted with one or more substituents selected from a hydroxy group, a carboxy group, a carbamoyl group, and a sulfo group) is preferred, and a halogen atom, a C1-C4 alkoxy group (hydroxy group, More preferably 1 or 2 or more substituents selected from a carboxy group, a carbamoyl group, and a sulfo group), and a halogen atom and a C1-C4 alkoxy group not substituted with a substituent are more preferable.
  • a chlorine atom and a methoxy group More preferred are a chlorine atom and a methoxy group.
  • acyl group a C1-C4 alkanoyl group is preferable, and examples thereof include a formyl group, an acetyl group, a propionyl group, and a butanoyl group.
  • the acylamino group is preferably an amino group substituted with one acyl group.
  • the azo compound represented by the above formula (1) or a salt thereof is preferably the azo compound represented by the above formula (1a) or a salt thereof.
  • a in Formula (1) can be represented by A 1 and (A 2 ) y (y represents 0 or 1) in Formula (1a).
  • R in Formula (1) can be represented by (R) z (z represents 0 or 1) in Formula (1a).
  • y + z 1.
  • y is preferably 0 and z is preferably 1.
  • a 1 and A 2 each independently represent a water-soluble substituent.
  • the water-soluble substituent has the same meaning as the water-soluble substituent in formula (1).
  • each R independently represents a hydrogen atom, a halogen atom, a carbamoyl group, a sulfamoyl group, a hydroxy group, an amino group, a cyano group, a nitro group, an acyl group, a C1-C4 alkyl group (hydroxy group, and carbamoyl).
  • a C1-C4 alkoxy group substituted with one or more substituents selected from a hydroxy group and a carbamoyl group
  • C1-C4 alkylsulfo group which may be substituted with one or more substituents selected from a hydroxy group and a carbamoyl group
  • C1-C4 alkylthio groups selected from a hydroxy group and a carbamoyl group
  • C1-C4 alkylamino groups hydroxy groups, and It may be substituted with one or more substituents selected from the moil group), or an acylamino group.
  • preferred R, more preferred R, still more preferred R, and even more preferred R are the same as in R of formula (1).
  • a and b represent the substitution positions of A 1 , A 2 or R.
  • a 1 is substituted at position a
  • a 2 or R is substituted at position b
  • a 1 is substituted at position b
  • a 2 or R is substituted at position a is doing. It is preferred that A 1 is substituted at the position of the substituent and A 2 or R b in the position of a, that A 1 is substituted at the position of a A 2 or R is substituted at the position of b More preferred. In the latter case, z is 1 and y is 0.
  • T, Q and x are the same as T, Q and x in the formula (1).
  • the compound of the present invention represented by the above formula (1) can be produced, for example, as follows.
  • x, A, T, R, Q, a, and b used as appropriate in the following formulas (2a), (3a), (4), and (5) have the same meaning as in the above formula (1).
  • the compound represented by the following formula (2a) is converted into a methyl- ⁇ -sulfonic acid derivative represented by the following formula (3a) using sodium bisulfite and formalin.
  • the compound represented by the following formula (2) is converted into a methyl- ⁇ -sulfonic acid derivative represented by the following formula (3) using sodium bisulfite and formalin.
  • the compound represented by the following formula (4) is diazotized by a conventional method, and the methyl- ⁇ -sulfonic acid derivative represented by the above-described formula (3a) is reacted with a reaction temperature of 0 to 15 ° C., pH 4
  • the compound represented by the following formula (5) is obtained by carrying out a coupling reaction at ⁇ 6, followed by a hydrolysis reaction at a reaction temperature of 80 to 95 ° C. and a pH of 10.5 to 11.5.
  • combination is a method according to the method as described in international publication 2011/122426.
  • the compound represented by the above formula (5) (2 mol) and a halogenated formate (1 mol), for example, paranitrophenyl chloroformate (1 mol) are condensed at a reaction temperature of 30 to 60 ° C. and a pH of 4 to 8.
  • the compound represented by the above formula (4) and the compound represented by the above formula (5) are preferably compounds represented by the following formulas (4a) and (5a), respectively.
  • the azo compound represented by (1a) can be obtained.
  • Tables 1 to 7 Specific examples of the compound of the present invention represented by the above formula (1) are shown in Tables 1 to 7 below. However, the present invention is not limited to these specific examples.
  • Tables 1 to 7 also show specific examples of the compounds of the present invention represented by the formula (1a). In this case, when y in the formula (1a) is 0, A in Tables 1 to 7 represents the formula (1a). corresponding to a 1 in).
  • the compound of the above formula (1) (including the compound of the formula (1a), the same shall apply hereinafter) also exists as a free acid or a salt thereof.
  • the salt of the compound represented by the formula (1) include salts with inorganic or organic cations.
  • Specific examples of the inorganic cation salt include alkali metal salts such as lithium salts, sodium salts, potassium salts and the like; and ammonium salts (NH 4 + ).
  • the salt of the quaternary ammonium represented, for example by following formula (6) is mentioned, It is not limited to these.
  • Z 1 to Z 4 each independently represents a hydrogen atom, a C1-C4 alkyl group, a hydroxy C1-C4 alkyl group, or a hydroxy C1-C4 alkoxy C1-C4 alkyl group, and Z 1 to Z At least one of 4 is a group other than a hydrogen atom.
  • examples of the C1-C4 alkyl group in Z 1 to Z 4 include a methyl group and an ethyl group.
  • examples of the hydroxy C1-C4 alkyl group include hydroxymethyl group, hydroxyethyl group, 3-hydroxypropyl group, 2-hydroxypropyl group, 4-hydroxybutyl group, 3-hydroxybutyl group, 2-hydroxy A butyl group etc. are mentioned.
  • examples of the hydroxy C1-C4 alkoxy C1-C4 alkyl group include hydroxyethoxymethyl group, 2-hydroxyethoxyethyl group, 3- (hydroxyethoxy) propyl group, 3- (hydroxyethoxy) butyl group, 2 -(Hydroxyethoxy) butyl group and the like can be mentioned.
  • alkali metal salts such as sodium, potassium and lithium
  • organic quaternary ammonium salts such as monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine and triisopropanolamine salts
  • Ammonium salt and the like.
  • lithium salts, sodium salts, and ammonium salts are more preferable.
  • the salt or free acid of the compound of formula (1) can be easily obtained by the following method or the like.
  • a water-soluble organic solvent such as acetone or C1-C4 alcohol is added to the reaction solution after the final step in the synthesis reaction of the compound of formula (1) or an aqueous solution containing a salt of the compound of formula (1).
  • the solid salt precipitated by the method of adding; the method of salting out by adding sodium chloride; and the like are filtered and separated to obtain the sodium salt of the compound of the above formula (1) as a wet cake.
  • an acid such as hydrochloric acid is added to adjust the pH appropriately, and the precipitated solid is separated by filtration, whereby the free acid of the compound of the above formula (1) is obtained.
  • a mixture of a free acid and a sodium salt in which a part of the compound of the formula (1) is a sodium salt is obtained.
  • an ammonium salt such as ammonium chloride is added, and an acid such as hydrochloric acid is added to adjust the pH appropriately to, for example, pH 1 to 3, By separating the precipitated solid by filtration, an ammonium salt of the compound of the above formula (1) can be obtained.
  • a mineral acid for example, hydrochloric acid, sulfuric acid, etc.
  • a salt, a potassium salt, a lithium salt, an ammonium salt, or a quaternary ammonium salt according to each added compound can be obtained.
  • a mixed salt of lithium salt and sodium salt, etc . for example, a mixed salt of lithium salt and sodium salt, etc .; and a mixture of lithium salt, sodium salt, and ammonium salt Salts and the like can also be prepared.
  • the salt of the compound of the above formula (1) may change the physical properties such as solubility or the ink performance when used as an ink depending on the type of the salt. For this reason, it is also preferable to select the type of salt according to the intended ink performance.
  • the compound of the present invention of the above formula (1) can be isolated as a solid free acid by adding a mineral acid such as hydrochloric acid, and the resulting free acid solid is water or, for example, hydrochloric acid water or the like.
  • a mineral acid such as hydrochloric acid
  • the resulting free acid solid is water or, for example, hydrochloric acid water or the like.
  • inorganic salts contained as impurities, such as sodium chloride and sodium sulfate, can be removed.
  • the free acid of the compound of the present invention obtained as described above is obtained by treating the obtained wet cake or its dried solid with a desired inorganic or organic base in water to give a salt of the corresponding compound. Solution.
  • Examples of the inorganic base include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, and potassium carbonate; and ammonium hydroxide (ammonia water). And the like.
  • Examples of the organic base include, but are not limited to, organic amines corresponding to the quaternary ammonium represented by the above formula (6), for example, alkanolamines such as diethanolamine and triethanolamine.
  • the compound of the present invention is suitable for dyeing natural and synthetic fiber materials or blended products, and also for producing inks for writing and ink jet recording.
  • the reaction liquid after completion of the final step in the synthesis reaction of the compound of the present invention represented by the formula (1) can be directly used for the production of the ink composition of the present invention.
  • the reaction solution or the like is dried by the above-described method or a spray drying method to isolate the compound, the obtained compound can be processed into an ink composition.
  • the compound of the above formula (1) is dissolved in water or a mixed solution (also referred to as an aqueous medium) of water and a water-soluble organic solvent (an organic solvent that can be mixed with water).
  • An ink preparation agent is added as necessary.
  • a metal cation chloride contained as an impurity, such as sodium chloride; sulfate, such as sodium sulfate; Is preferred.
  • the total content of sodium chloride and sodium sulfate is about 1% by mass or less with respect to the total mass of the compound of formula (1), and the lower limit is 0% by mass, that is, below the detection limit of the detection instrument. Good.
  • a method for producing a compound having a small amount of inorganic impurities for example, a method using a known reverse osmosis membrane; or a dried product or wet cake of the compound of the present invention, for example, acetone or C1-C4 alcohol (for example, methanol, ethanol, In addition to a water-soluble organic solvent such as isopropanol or the like, or a water-containing water-soluble organic solvent, suspension purification or crystallization methods, and the like can be mentioned. Desalination treatment or the like may be performed by these methods.
  • the compound of the above formula (1) is usually 0.1 to 20% by mass, preferably 1 to 10% by mass, more preferably 2 to 8% by mass in the total mass of the ink composition. contains.
  • the ink composition of the present invention is prepared using water as a medium, and may optionally contain a water-soluble organic solvent and an ink preparation agent as long as the effects of the present invention are not impaired.
  • the water-soluble organic solvent dissolves the dye; prevents the composition from drying (maintains a wet state); adjusts the viscosity of the composition; promotes penetration of the dye into the recording material; adjusts the surface tension of the composition; It is used for the purpose of effects such as defoaming of a product, and is preferably contained in the ink composition of the present invention.
  • ink preparation agent examples include antiseptic / antifungal agents, pH adjusting agents, chelating reagents, rust preventive agents, ultraviolet absorbers, viscosity adjusting agents, dye dissolving agents, antifading agents, surface tension adjusting agents, antifoaming agents, etc.
  • Known additives may be mentioned.
  • the content of the water-soluble organic solvent is 0 to 60% by mass, preferably 10 to 50% by mass, and the ink preparation agent is 0 to 20% by mass, preferably 0%, based on the total mass of the ink composition of the present invention. It is preferable to use up to 15% by mass.
  • the balance other than the compound of the above formula (1), the water-soluble organic solvent, and the ink preparation agent is water.
  • water-soluble organic solvent examples include C1-C4 alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol and tert-butanol; N, N-dimethylformamide, N Amides such as 1, N-dimethylacetamide; 2-pyrrolidone, N-methyl-2-pyrrolidone, hydroxyethyl-2-pyrrolidone, 1,3-dimethylimidazolidin-2-one or 1,3-dimethylhexahydropyrimido Heterocyclic ketones such as -2-one; ketones or ketoalcohols such as acetone, methyl ethyl ketone, 2-methyl-2-hydroxypentan-4-one; cyclic ethers such as tetrahydrofuran, dioxane; ethylene glycol, 1,2- or 1,3-propylene glycol, 1, -Or mono having
  • the water-soluble organic solvent includes substances that are solid at room temperature, such as trimethylolpropane.
  • the substance or the like shows water solubility, and an aqueous solution containing the substance or the like shows the same properties as the water-soluble organic solvent and can be used with the expectation of the same effect. Therefore, in this specification, for the sake of convenience, such a solid substance is included in the category of a water-soluble organic solvent as long as it can be used for the same purpose as described above.
  • water-soluble organic solvent Preferred as the above water-soluble organic solvent are isopropanol, glycerin, mono-, di- or triethylene glycol, dipropylene glycol, 2-pyrrolidone, hydroxyethyl-2-pyrrolidone, 1,3-dimethylimidazolidin-2-one N-methyl-2-pyrrolidone, trimethylolpropane and butyl carbitol, more preferably isopropanol, glycerin, diethylene glycol, 2-pyrrolidone, N-methyl-2-pyrrolidone and butyl carbitol.
  • These water-soluble organic solvents are used alone or in combination.
  • antiseptic / antifungal agent examples include organic sulfur, organic nitrogen sulfur, organic halogen, haloallylsulfone, iodopropargyl, N-haloalkylthio, benzothiazole, nitrile, pyridine, 8-oxyquinoline, isothiazoline, dithiol, pyridine oxide, nitropropane, organotin, phenol, quaternary ammonium salt, triazine, thiadiazine, anilide, adamantane, dithiocarbamate, bromo Indanone compound, benzyl bromacetate compound, inorganic salt compound and the like can be mentioned.
  • An example of the organic halogen compound is sodium pentachlorophenol.
  • Examples of pyridine oxide compounds include sodium 2-pyridinethiol-1-oxide.
  • Examples of the isothiazoline compounds include 1,2-benzisothiazolin-3-one, 2-n-octyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazoline-3-one, 5 -Chloro-2-methyl-4-isothiazolin-3-one magnesium chloride, 5-chloro-2-methyl-4-isothiazolin-3-one calcium chloride, 2-methyl-4-isothiazolin-3-one calcium chloride, etc. Can be mentioned.
  • antiseptic / antifungal agents include sodium acetate, sodium sorbate, sodium benzoate and the like; and trade names Proxel RTM GXL (S) and Proxel RTM XL-2 (S) manufactured by Arch Chemical Co., Each is listed. In the present specification, the superscript “RTM” means a registered trademark.
  • any substance can be used as long as it can control the pH of the ink in the range of 6.0 to 11.0 for the purpose of improving the storage stability of the ink.
  • alkanolamines such as diethanolamine and triethanolamine
  • hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide and potassium hydroxide
  • ammonium hydroxides or alkali metals such as lithium carbonate, sodium carbonate and potassium carbonate And carbonates
  • aminosulfonic acids such as taurine; and the like.
  • chelating reagent examples include disodium ethylenediaminetetraacetate, sodium nitrilotriacetate, sodium hydroxyethylethylenediaminetriacetate, sodium diethylenetriaminepentaacetate, sodium uracil diacetate, and the like.
  • rust preventive examples include acid sulfite, sodium thiosulfate, ammonium thioglycolate, diisopropylammonium nitrite, pentaerythritol tetranitrate, dicyclohexylammonium nitrite and the like.
  • the ultraviolet absorber examples include benzophenone compounds, benzotriazole compounds, cinnamic acid compounds, triazine compounds, and stilbene compounds.
  • a compound that absorbs ultraviolet rays such as a benzoxazole-based compound and emits fluorescence, a so-called fluorescent whitening agent, and the like can also be used.
  • examples of the viscosity modifier include water-soluble polymer compounds in addition to water-soluble organic solvents, and examples thereof include polyvinyl alcohol, cellulose derivatives, polyamines, and polyimines.
  • dye solubilizer examples include urea, ⁇ -caprolactam, ethylene carbonate, and the like. Of these, urea is preferably used.
  • the anti-fading agent is used for the purpose of improving image storage stability.
  • various organic and metal complex antifading agents can be used.
  • organic anti-fading agents include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines, amines, indanes, chromans, alkoxyanilines, and heterocycles, and metal complexes Examples thereof include nickel complexes and zinc complexes.
  • Examples of the surface tension adjusting agent include surfactants, and examples include anionic surfactants, amphoteric surfactants, cationic surfactants, and nonionic surfactants.
  • anionic surfactants include alkyl sulfocarboxylates, ⁇ -olefin sulfonates, polyoxyethylene alkyl ether acetates, N-acyl amino acids and salts thereof, N-acyl methyl taurate, alkyl sulfate polyoxyalkyl ethers Sulfate, alkyl sulfate polyoxyethylene alkyl ether phosphate, rosin acid soap, castor oil sulfate ester, lauryl alcohol sulfate ester, alkylphenol type phosphate ester, alkyl type phosphate ester, alkylaryl sulfonate, diethylsulfosuccinate Salts, diethylhexylsulfosuccinate, dioctylsulfosuccinate and the like.
  • Examples of the cationic surfactant include 2-vinylpyridine derivatives and poly-4-vinylpyridine derivatives.
  • Amphoteric surfactants include lauryldimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, coconut oil fatty acid amidopropyldimethylaminoacetic acid betaine, polyoctylpolyaminoethylglycine, and other imidazoline derivatives. Etc.
  • Nonionic surfactants include ethers such as polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene dodecylphenyl ether, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene alkyl ether; Ester systems such as polyoxyethylene oleate, polyoxyethylene distearate, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, polyoxyethylene monooleate, polyoxyethylene stearate; 2,4,7,9-tetramethyl-5-decyne-4,7-diol, 3,6-dimethyl-4-octyne-3,6-diol, 3,5-dimethyl -1-hexyne-3-acetylene glycol (alcohol) -based ol; Nissin Chemical Industry Co., Ltd. trade name Surfynol
  • antifoaming agents include highly oxidized oils, glycerin fatty acid esters, fluorines, and silicone compounds.
  • the surface tension of the ink composition of the present invention is usually 25 to 70 mN / m, preferably 25 to 60 mN / m, and the viscosity is preferably 30 mPa ⁇ s or less, and more preferably 20 mPa ⁇ s or less.
  • the ink composition of the present invention there is no particular limitation on the order of dissolving each agent such as an additive.
  • the water used for preparing the ink composition is preferably water with few impurities such as ion exchange water and distilled water. Further, if necessary, after the ink composition is prepared, fine filtration may be performed using a membrane filter or the like to remove impurities in the ink composition.
  • fine filtration may be performed using a membrane filter or the like to remove impurities in the ink composition.
  • the pore size of the filter used for microfiltration is usually 1 ⁇ m to 0.1 ⁇ m, preferably 0.8 ⁇ m to 0.1 ⁇ m.
  • the ink composition containing the compound of the present invention is suitable for use in printing, copying, marking, writing, drafting, stamping, or recording (printing), particularly inkjet recording.
  • the ink composition of the present invention is less likely to precipitate solids even when dried in the vicinity of the nozzles of the recording head of an ink jet printer, and for this reason, the recording head is also less likely to block.
  • the ink jet recording method of the present invention As a method for recording on a recording material by the ink jet recording method of the present invention, the following method may be mentioned. That is, a container filled with the ink composition of the present invention is loaded into a predetermined position of an ink jet printer, the ink composition of the present invention is used as ink, and ink droplets of the ink are ejected according to a recording signal to be recorded. This is a method for recording on a material.
  • Some inkjet printers use, for example, a piezo method using mechanical vibration; a bubble jet (registered trademark) method using bubbles generated by heating; and the like.
  • the ink jet recording method of the present invention can be used by any method.
  • ink composition of the present invention can also be used as such an ink set. Further, the ink composition of the present invention may be used for one of the ink sets, and a known ink (composition) may be used for the other.
  • the ink composition of the present invention may be a yellow ink composition containing the compound of the present invention and a known yellow dye for the purpose of fine-tuning the hue within a range that does not impair the effects obtained by the present invention.
  • the compound of the present invention can be used in combination with a magenta dye or a cyan dye for the purpose of toning inks of other colors, such as black ink, or for preparing red ink or green ink.
  • the ink composition of the present invention can be used in combination with inks of various colors such as magenta, cyan, and, if necessary, green, blue (or violet), red, and black. .
  • each color ink may be filled in each container, and these containers may be loaded into a predetermined position of the ink jet printer and used for ink jet recording.
  • Examples of the recording material used in the inkjet recording method of the present invention include information transmission sheets such as paper and film, fibers and fabrics (cellulose, nylon, wool, etc.), leather, base materials for color filters, and the like.
  • a transmission sheet is preferred.
  • the information transmission sheet is not particularly limited, and a plain paper as well as a surface-treated sheet, specifically, a paper, synthetic paper, a substrate such as a film provided with an ink receiving layer, or the like is used.
  • the ink receiving layer is a layer having an action such as absorbing ink and accelerating its drying.
  • the ink receiving layer is formed by, for example, a method of impregnating or coating the base material with a cationic polymer; inorganic fine particles capable of absorbing the pigment in the ink, together with a hydrophilic polymer such as polyvinyl alcohol or polyvinylpyrrolidone, on the surface of the base material. It is provided by the method of coating; Examples of the material of the inorganic fine particles that can absorb the coloring matter in the ink include porous silica, alumina sol, and special ceramics.
  • the information transmission sheet having such an ink receiving layer is usually called an inkjet exclusive paper, an inkjet exclusive film, a glossy paper, a glossy film or the like.
  • Typical examples of commercially available information transmission sheets having an ink receiving layer are Canon Inc., trade name Professional Photo Paper, Canon Photographic Paper / Glossy Pro [Platinum Grade], and Glossy Gold; Seiko Epson ( Product name Photo Paper Krispia (high gloss), Photo Paper (Gloss); Nihon Hewlett-Packard Co., Ltd. Product Name Advanced Photo Paper (Gloss); Fuji Film Co., Ltd. Pro; manufactured by Brother Industries, Ltd., trade name: photographic glossy paper BP71G; Also, plain paper means paper that is not particularly provided with an ink receiving layer, and many different types are commercially available depending on the application.
  • plain paper As Typical plain papers, double-sided plain plain paper (manufactured by Seiko Epson Corporation); PB PAPER GF-500 (manufactured by Canon Inc.); Multipurpose Paper, All-in-one Printing Paper ( Hewlett Packard).
  • plain paper copy (PPC) paper or the like whose use is not limited to ink jet recording is also plain paper.
  • the colored product of the present invention comprises: (a) the water-soluble azo compound of the present invention or a salt thereof; (b) the ink composition of the present invention containing the compound or a salt thereof;
  • the ink composition of the present invention containing an organic solvent means a colored substance.
  • the substance to be colored is not particularly limited, and examples thereof include, but are not limited to, the recording material described above.
  • the above-mentioned recording material is colored.
  • the coloring method for the substance is not particularly limited, and examples thereof include a printing method such as a dip dyeing method, a textile printing method, and screen printing, and the ink jet recording method of the present invention.
  • the ink jet recording method of the present invention is preferable.
  • a colored body colored by the ink jet recording method of the present invention is preferable.
  • the water-soluble azo compound of the present invention represented by the above formula (1) or a salt thereof is excellent in solubility in water or a water-soluble organic solvent. Moreover, it has the characteristic that the filterability with respect to a membrane filter, for example in the process of manufacturing the ink composition of this invention is favorable.
  • the ink composition of the present invention is very clear on a recording material such as plain paper and an information transmission sheet having an ink receiving layer, has a high saturation and printing density, and is capable of producing a yellow recorded image of an ideal hue. give. Therefore, it is also possible to faithfully reproduce a photographic color image on paper.
  • the ink composition of the present invention has very good storage stability without solid deposition, physical property change, hue change, etc. after long-term storage.
  • the ink composition of the present invention uses a continuous ink jet printer, and is used physically even when the ink is recirculated at a relatively long time interval or intermittently used by an on-demand ink jet printer. No change in properties.
  • the image recorded on the information transmission sheet having the ink receiving layer by the ink composition of the present invention has various fastnesses such as water resistance, moisture resistance, ozone gas resistance, abrasion resistance and light resistance, particularly light resistance.
  • the water-soluble azo compound of the present invention represented by the formula (1) or a salt thereof and the ink composition of the present invention containing the same are used for various recording ink applications, particularly for ink jet recording. Very useful.
  • Example 2 (Process 1) In the above Example 1 (Step 1), instead of using 24.9 parts of 5-amino-2-chlorobenzenesulfonic acid, 24.4 parts of 3-amino-4-methoxybenzenesulfonic acid, 5-chloro-2- ( 80 parts of an azo compound represented by the following formula (9) was obtained as a wet cake in the same manner as in Step 1 of Example 1 except that 26.2 parts of 3-sulfopropoxy) aniline was used.
  • Example 3 (Process 1) In Example 1 (Step 1) above, instead of using 26.2 parts of 5-chloro-2- (3-sulfopropoxy) aniline, 31.1 parts of 5-bromo-2- (3-sulfopropoxy) aniline were used. Except for using, in the same manner as in Step 1 of Example 1, 80 parts of an azo compound represented by the following formula (12) was obtained as a wet cake.
  • Example 4 (Process 1) In Example 1 (Step 1) above, instead of using 26.2 parts of 5-chloro-2- (3-sulfopropoxy) aniline, 23.0 parts of 5-chloro-2- (3-carbopropoxy) aniline were used. Except for using, in the same manner as in Step 1 of Example 1, 80 parts of an azo compound represented by the following formula (14) was obtained as a wet cake.
  • Example 5 [(B) Preparation of ink] [Example 5] Using the azo compound of the present invention obtained in Example 1 above [sodium salt of the compound represented by formula (8)] as a dye, the composition shown in Table 8 below was mixed to give a solution. An ink composition of the invention was obtained. The obtained ink composition was filtered through a 0.45 ⁇ m membrane filter to remove impurities, and a test ink was prepared. The pH of the test ink was in the range of 8.0 to 9.5. Further, in Table 8 below, “surfactant” used was the trade name Surfinol RTM 104PG50 manufactured by Nissin Chemical Co., Ltd. The ink prepared using the compound obtained in Example 1 is referred to as Example 5.
  • Example 6 An ink prepared by mixing the compositions shown in Table 8 below and using the compound obtained in Example 2 is referred to as Example 6.
  • Ink prepared using the compound obtained in Example 4 was prepared by mixing the composition shown in Table 9 below and using the compound obtained in Example 3 as Example 7. Is taken as Example 8.
  • “Surfactant” is trade name Surfinol RTM 104PG50 manufactured by Nissin Chemical Co., Ltd.
  • Glossy paper 1 manufactured by Canon Inc., trade name: Canon photo paper, platinum grade (PT-201) Glossy paper 2: Seiko Epson, product name: Photographic paper Krispia
  • the water-soluble azo compound of the present invention or a salt thereof, and the ink composition of the present invention containing the compound have a clear hue compared to conventional dyes, and have a yellow print density. It can be seen that the value is high and the color developability is excellent.
  • the water-soluble azo compound of the present invention or a salt thereof, which is a yellow dye, and the yellow ink composition of the present invention containing the same are recorded images having excellent color developability such as saturation, brightness, and print density on glossy paper give. Further, since an alkoxyaniline substituted with a water-soluble substituent such as a sulfo group is used in place of a raw material such as o-anisidine used for an existing dye, few compounds are generated due to decomposition of the pigment. Therefore, the compound and the ink composition containing the compound are very useful for various recording applications, particularly for inkjet recording applications.

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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)
  • Ink Jet (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

　La présente invention concerne un colorant (composé) jaune hydrosoluble qui possède une solubilité élevée dans l'eau, une excellente solidité à la lumière et d'excellentes propriétés de coloration, telles que la saturation et la densité d'impression; une composition d'encre jaune contenant ce colorant jaune, ladite composition étant utilisée dans diverses applications d'impression, en particulier l'impression par jet d'encre; et un corps coloré ayant été coloré par cette composition d'encre. L'invention concerne spécifiquement un composé azoïque représenté par la formule (III) ou un sel de celui-ci. (Dans la formule, A1, A2 et T représentent chacun indépendamment un substituant hydrosoluble; chaque Q représente indépendamment un atome d'hydrogène, un atome d'halogène, un groupe sulfo ou analogue; chaque R représente indépendamment un atome d'halogène, un groupe alcoxy en C1-4 ou analogue; y représente 0 ou 1, et z représente 0 ou 1, y + z = 1; x représente un nombre entier compris entre 2 et 4; et a et b représentent les positions de substitution de A1, A2 ou R).
PCT/JP2015/072586 2014-08-08 2015-08-07 Compose azoique hydrosoluble ou sel de celui-ci, composition d'encre et corps colore WO2016021730A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016186196A1 (fr) * 2015-05-20 2016-11-24 日本化薬株式会社 Composés azoïques, film polarisant à base de colorant le contenant, et plaque polarisante
WO2016186195A1 (fr) * 2015-05-20 2016-11-24 日本化薬株式会社 Composés azoïques, film polariseur de type colorant et plaque de polariseur comprenant ceux-ci
WO2016186194A1 (fr) * 2015-05-20 2016-11-24 日本化薬株式会社 Composés azoïques, film polarisant à base d'un colorant les contenant, et lame polarisante
WO2021235160A1 (fr) * 2020-05-19 2021-11-25 日本化薬株式会社 Encre, impression et procédé d'enregistrement à jet d'encre

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004075767A (ja) * 2002-08-13 2004-03-11 Konica Minolta Holdings Inc インクジェットインク、インクジェットインクセット及びインクジェット記録方法
WO2011122426A1 (fr) * 2010-03-30 2011-10-06 日本化薬株式会社 Composé azo hydrosoluble ou sel de ce composé, composition d'encre, et corps coloré
JP2012167154A (ja) * 2011-02-10 2012-09-06 Ricoh Co Ltd インクジェット記録用インクセット、該インクセットを用いたインクジェット記録方法及び記録物

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012211086A (ja) * 2011-03-30 2012-11-01 Toray Ind Inc 関節リウマチの治療剤又は予防剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004075767A (ja) * 2002-08-13 2004-03-11 Konica Minolta Holdings Inc インクジェットインク、インクジェットインクセット及びインクジェット記録方法
WO2011122426A1 (fr) * 2010-03-30 2011-10-06 日本化薬株式会社 Composé azo hydrosoluble ou sel de ce composé, composition d'encre, et corps coloré
JP2012167154A (ja) * 2011-02-10 2012-09-06 Ricoh Co Ltd インクジェット記録用インクセット、該インクセットを用いたインクジェット記録方法及び記録物

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016186196A1 (fr) * 2015-05-20 2016-11-24 日本化薬株式会社 Composés azoïques, film polarisant à base de colorant le contenant, et plaque polarisante
WO2016186195A1 (fr) * 2015-05-20 2016-11-24 日本化薬株式会社 Composés azoïques, film polariseur de type colorant et plaque de polariseur comprenant ceux-ci
WO2016186194A1 (fr) * 2015-05-20 2016-11-24 日本化薬株式会社 Composés azoïques, film polarisant à base d'un colorant les contenant, et lame polarisante
KR20180006925A (ko) * 2015-05-20 2018-01-19 닛뽄 가야쿠 가부시키가이샤 아조 화합물 및 그것들을 함유하는 염료계 편광막 그리고 편광판
JPWO2016186194A1 (ja) * 2015-05-20 2018-03-08 日本化薬株式会社 アゾ化合物及びそれらを含有する染料系偏光膜並びに偏光板
KR102581552B1 (ko) 2015-05-20 2023-09-21 닛뽄 가야쿠 가부시키가이샤 아조 화합물 및 그것들을 함유하는 염료계 편광막 그리고 편광판
WO2021235160A1 (fr) * 2020-05-19 2021-11-25 日本化薬株式会社 Encre, impression et procédé d'enregistrement à jet d'encre

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