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WO2011030810A1 - Dérivé de colorant, colorant, et procédé de coloration - Google Patents

Dérivé de colorant, colorant, et procédé de coloration Download PDF

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Publication number
WO2011030810A1
WO2011030810A1 PCT/JP2010/065478 JP2010065478W WO2011030810A1 WO 2011030810 A1 WO2011030810 A1 WO 2011030810A1 JP 2010065478 W JP2010065478 W JP 2010065478W WO 2011030810 A1 WO2011030810 A1 WO 2011030810A1
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WO
WIPO (PCT)
Prior art keywords
group
dye
compound
pigment
derivative
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2010/065478
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English (en)
Japanese (ja)
Inventor
道衛 中村
哲男 福田
敦 野上
宏光 柳本
雅則 高鴨
尚之 坂井
利江 大久保
慎吾 桐
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dainichiseika Color and Chemicals Mfg Co Ltd
Original Assignee
Dainichiseika Color and Chemicals Mfg Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dainichiseika Color and Chemicals Mfg Co Ltd filed Critical Dainichiseika Color and Chemicals Mfg Co Ltd
Priority to KR1020127009150A priority Critical patent/KR101406378B1/ko
Priority to JP2011514930A priority patent/JP5465718B2/ja
Priority to CN201080040152.4A priority patent/CN102482513B/zh
Publication of WO2011030810A1 publication Critical patent/WO2011030810A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0008—Coated particulate pigments or dyes with organic 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters

Definitions

  • the present invention relates to a pigment derivative, a colorant, and a coloring method. More specifically, a dye derivative in which a compound having a methine group or an amino group is linked to the molecular structure of a water-insoluble dye via an alkylene group, a colorant containing the same, a coloring method for an article using the same, and a colored article It is about.
  • dyes used for coloring articles dyes that are soluble in water and solvents, and pigments that are insoluble in those media and finely dispersed in fine particles are usually used.
  • dyes have many simple pigments as molecular structures, and the color has excellent transparency and sharpness, but has a problem in fastness such as light resistance and heat resistance.
  • pigments have a lower color tone and sharpness than dyes, and many have crystal forms, some of which are unstable to organic solvents and heat, and crystal transitions and particles become coarse, resulting in color changes.
  • Liquid pigments of pigments are often dispersed in liquid media such as solvents and water and tend to settle or aggregate, and even if improved with a dispersion aid, they will aggregate for a long time. It had drawbacks, such as a problem in sex.
  • reddish blue ⁇ -type copper phthalocyanine pigment (CI Pigment Blue 15: 6) is used as a blue pigment used for forming a blue pixel of an image display material of a color filter. Slightly unstable to heat. For this reason, monosulfonated copper phthalocyanine is often used as an additive for suppressing pigment crystal transition and crystal growth, but it tends to have a green hue and lower saturation. It is not preferable in terms of color tone for blue pixels of taste blue. That is, there is a demand for a pigment derivative that can achieve a better color tone without impairing the color tone of the original pigment.
  • an object of the present invention is to develop a pigment derivative based on an existing pigment skeleton in order to improve the fastness and color tone of these pigments economically and efficiently.
  • the present inventors have found the following to arrive at the present invention when synthesizing a pigment derivative. That is, by reacting a compound (B) for forming an alkylene group with the water-insoluble dye (A) and a compound (C) having a reactive methine group or amino group, a dye molecule such as a pigment and the alkylene A new dye derivative in which a group is bonded by a carbon-carbon bond and the residue of the compound (C) is linked to the other end of the alkylene group is obtained, and by using these, the above-mentioned problems can be solved. I found.
  • the present invention is a derivative of a water-insoluble dye used as a colorant, which is a water-insoluble dye (A) and an aldehyde compound (B) that can react with the water-insoluble dye (A) to form an alkylene group.
  • a hydrocarbon compound having a methine group (—CH ⁇ ) having an easily replaceable hydrogen group and its derivative (C-1), an amino compound having a reactive amino group and a derivative (C-2) thereof A derivative of a dye obtained by reacting any one of the compounds (C) selected from the above, wherein the water-insoluble dye (A) molecule and the compound (C) residue are linked via the alkylene group.
  • a pigment derivative characterized in that
  • the aldehyde compound (B) is at least one selected from the group consisting of paraformaldehyde, trioxane, formaldehyde, formalin, glyoxal, and alkyl aldehyde having 1 to 10 carbon atoms.
  • the compound (C) is an amino acid compound having 1 to 10 carbon atoms, an amino compound having 1 to 20 carbon atoms, an aminotriazine compound having 0 to 10 carbon atoms, a carboamide compound having 1 to 20 carbon atoms, or a 1 to 20 carbon atom.
  • the number of compound (C) residues bonded to the water-insoluble dye (A) molecule via an alkylene group is 1 to 6.
  • the water-insoluble pigment (A) is at least one selected from the group consisting of organic pigments, vat dyes and disperse dyes.
  • the water-insoluble dye (A) is phthalocyanine, anthraquinone, perylene, perinone, dioxazine, quinacridone, diketopyrrolopyrrole, indigo / thioindigo, quinophthalone, isoindolinone, metal complex And at least one selected from the group consisting of insoluble azo dyes and high molecular weight azo dyes.
  • the present invention provides a liquid medium comprising any one of the above-described dye derivatives and a dilution medium, an organic solvent system, an aqueous system, or a water-hydrophilic organic solvent mixed solvent system, or a polymerization medium.
  • a colorant comprising at least one of a polymerizable liquid medium comprising a polymerizable oligomer or a polymerizable monomer, or a resin medium comprising a synthetic resin.
  • Preferred examples of such a colorant include the following forms.
  • it contains a polymer system dispersant or a low molecular weight dispersion aid as a dispersion aid.
  • dyeing agent printing agent, paint, printing ink, stationery, paint, resin colorant, electrophotographic printing developer, electrostatic printing developer or color filter pixel forming ink It must be either.
  • the present invention provides a coloring method selected from dyeing, textile printing, painting, printing, writing, drawing, resin coloring, electrophotographic printing, electrostatic printing, or a color filter pixel forming method. Further, the present invention provides a method for coloring an article characterized by using any one of the above colorants.
  • the present invention when coloring a color filter substrate by a coloring method for forming pixels by any one of a photoresist method, an inkjet printing method, a printing method, a transfer method, or a pasting method, Provided is a method for coloring an article characterized by using any of the colorants.
  • the dye solution or dispersion (hereinafter collectively referred to as “base color”) used for the colorant is any one of the above-described dye derivatives, and further, if necessary, a pigment, an oil
  • a polymerizable oligomer a polymerizable liquid medium comprising a polymerizable monomer;
  • a base color characterized in that a resin medium comprising a plasticizer, an oligomer and a synthetic resin is used, and if necessary, a polymer system dispersant and a low molecular dispersion aid are used as a dispersion aid.
  • the colorant contains any one of the above-described pigment derivatives as a colorant, and if necessary, further contains a pigment, an oil-soluble dye or a water-soluble dye.
  • Liquid medium composed of mixed solvent system of hydrophilic organic solvent; Polymerizable liquid medium composed of polymerizable oligomer and polymerizable monomer; Resin medium composed of plasticizer, oligomer and synthetic resin, and / or containing pigment derivative
  • a thermoplastic polymer a reactive polymer, a reactive oligomer, a polymerizable monomer and a cross-linking agent using the base color and / or as a film-forming material.
  • a colorant characterized by containing a material and further containing a curing catalyst, a polymerization catalyst and the like as required.
  • the present invention provides a colored article formed by a known coloring method using any one of the above-described colorants of the present invention.
  • the carbon atom of the alkylene group is linked to the carbon atom of the water-insoluble dye to form a carbon-carbon bond, and in a more preferred form, it has a hydrophilic group, so it is soluble in an aqueous medium.
  • a pigment a pigment derivative excellent in light resistance as compared with a dye is provided.
  • the pigment derivative of the present invention provides a deep color effect depending on the number of substituents introduced, characteristics are also shown in the color tone. It is possible to provide a sky blue color excellent in fastness used in the printing / recording field, resin coloring field, etc., and is useful for various applications.
  • the present invention depending on the nature of various substituents introduced into the residue of the compound (C) linked to the water-insoluble dye (A) molecule, it is possible to suppress pigment crystal transition and crystal growth. It is possible to provide a pigment derivative that is effective as an additive. Therefore, according to the present invention, the function of a dispersion aid or the like that improves the dispersibility of the pigment of the organic solvent-based pigment dispersion color, decreases the viscosity of the dispersion, improves dispersion stability, long-term storage stability, etc. A colorant containing a sex additive is obtained. Furthermore, since these can be obtained from derivatives based on existing dye skeletons, they can be carried out economically and efficiently, and are extremely useful from a practical viewpoint.
  • the dye derivative of the present invention comprises a water-insoluble dye (A), an aldehyde compound (B) that reacts with the dye (A) to form an alkylene group, a compound and its derivative (C), and is water-insoluble.
  • the dye (A) molecule and the compound (C) residue are a derivative of a dye formed by linking via the alkylene group. That is, a pigment derivative having a structure in which the residue of compound (C) capable of imparting various properties to the molecular structure of water-insoluble pigment (A) is linked by an alkylene group (carbon-carbon bond) is provided. .
  • the compound (C) is a hydrocarbon compound having a methine group (—CH ⁇ ) having an easily replaceable hydrogen group and its derivative (C-1), an amino compound having a reactive amino group and its derivative (C -2).
  • the structure of the dye derivative and the compound (C) linked to the dye molecule are configured as described above, and as described above, as a derivative based on an existing dye skeleton, In particular, it is possible to realize a pigment derivative excellent in deep color effect and characteristics without changing the basic color tone.
  • combining method of the pigment derivative of this invention and each component to be used are demonstrated.
  • the dye derivative of the present invention has a structure in which the molecular structure of the water-insoluble dye (A) and the compound (C) residue are bonded via an alkylene group that is a residue of the aldehyde compound (B).
  • Examples of the method for synthesizing the dye derivative include the following methods. (1) A water-insoluble dye (A), an aldehyde compound (B) which is an alkylene-forming reactive compound, and a compound (C) having an active hydrogen group capable of condensation reaction are dissolved in a reaction medium and simultaneously reacted to synthesize. Method.
  • the water-insoluble dye (A) is dissolved in the reaction medium, and the aldehyde compound (B) is added and reacted to form an alkylene group on the dye.
  • the compound (C) is reacted with the aldehyde compound (B), the reaction product is optionally isolated, and an alkylene group is added to the compound (C).
  • a method in which the water-insoluble dye (A) is added or the solution is mixed and reacted to synthesize.
  • Water-insoluble dye (A) The water-insoluble dye (A) that is a constituent material of the dye derivative of the present invention will be described.
  • the dye (A) the molecular structure or the dye molecular structure forming the dye main body part in the produced dye derivative has a dye molecule structure that is not bonded with a hydrophilic group, in other words, a water-insoluble dye molecule structure.
  • a water-insoluble dye molecule structure Use what you have.
  • Specific examples include the molecular structure of water-insoluble pigments used as known organic pigments, vat dyes, dispersible dyes, and the like.
  • vat dyes, naphthol dyes, and the like are used by being solubilized in water as precursors at the time of dyeing, but are water-insoluble dyes in a colored state and are used in the dye (A) used in the present invention. included.
  • the light fastness of a dye is displayed in the class from 8th class to 1st class, or E class, VG class, G class, F class, P class.
  • the water-insoluble dye (A) used as the dye matrix is generally classified into grade 6 or grade G, preferably grade 7 or grade VG, more preferably grade 8 or more, depending on the application. It is preferred that a dye of grade E or higher is selected.
  • the pigment molecular structure with higher fastness is superior in light resistance, but in addition, the pigment molecule has a crystal structure formation and exhibits a strong pigment, and the size of the pigment particles Some of them exhibit more robustness.
  • the dye (A) used in the present invention a pigment considered to have high fastness due to the molecular structure of the pigment provides excellent light resistance when the dye derivative of the present invention is constituted as a final form. it is conceivable that.
  • the molecular structure of the preferred water-insoluble dye (A) used in the present invention has a substitution position into which a linking group formed by the aldehyde compound (B) described later can be introduced and has high light resistance.
  • Organic pigments classified as higher pigments and vat dyes having a chemical structure similar to higher pigments as the basic skeleton are preferably selected.
  • water-insoluble dye (A) used in the present invention examples include the following.
  • CI pigment is abbreviated as“ P ”and blue is abbreviated as“ B ”. Therefore, C.I. I. Pigment Blue is abbreviated as “PB”.
  • PB water-insoluble dye
  • G green
  • Y yellow
  • O orange
  • V violet
  • PB15 aluminum phthalocyanine blue
  • PB16 aluminum phthalocyanine blue
  • PB16, PG7, PG36 poly (13-16) bromocopper phthalocyanine green, PG58, etc.
  • Vat Yellow is abbreviated as “VY”.
  • VY Vat Yellow
  • Quinacridone series As a diketopyrrolopyrrole system, PR254, PR255, etc .
  • As an indigo / thioindigo system PR87, PV36;
  • PY139, PY109 such as isoindolinone; etc.
  • PY138 is Te.
  • a coloring compound having a chemical structure similar to the above-mentioned higher-class pigments as a basic skeleton can also be used.
  • aldehyde compound (B) The aldehyde compound (B) which is a constituent material of the pigment derivative of the present invention will be described.
  • the aldehyde compound (B) can react with the dye (A) to form an alkylene group. Specifically, in the first stage addition reaction, a hydroxyl group such as a methylol group, an alkoxymethyl group, or a halogenomethyl group or a reactive derivative group thereof is formed, and then the second stage dehydration, dealcoholization, A compound in which the water-insoluble dye (A) described above and a compound (C) residue described below are linked via an alkylene group by a condensation reaction such as dehydrohalogenation.
  • aldehyde compound (B) examples include formaldehyde, trioxane, paraformaldehyde, formalin, glyoxal, or an alkyl aldehyde having 1 to 10 carbon atoms. Of these, paraformaldehyde is particularly preferable.
  • Compound (C) The compound (C) which is a constituent material of the pigment derivative of the present invention will be described.
  • the compound (C) is selected from the group consisting of the following compounds and derivatives.
  • the methine group of the hydrocarbon compound having a methine group in (C-1) has an easily replaceable hydrogen group, it is formed from the aldehyde group of the aldehyde compound (B) described above or the aldehyde compound (B). It can be dehydrated with a hydroxyl group such as a methylol group to form a bond.
  • the hydrocarbon compound having a methine group include a hydrocarbon group having an easily replaceable hydrogen atom of an aromatic skeleton. Specific examples include phenol compounds (carbon number: 6-20) and N, N-disubstituted aniline compounds (carbon number: 8-20), which are preferably used.
  • Preferred amino compounds having a reactive amino group in the above (C-2) are amino acid compounds (carbon number: 1 to 10), amino compounds (carbon number: 1 to 20), aminotriazine compounds (carbon number: 0-10), carboamide compounds (carbon number: 1-20), carboimide compounds having 1-20 carbon atoms (excluding phthalimide), sulfamic acid compounds (carbon number: 0-10), and the like. Also with these compounds, bonds can be formed by a dehydration reaction as in the case of the above-mentioned compound (C-1).
  • substituent It is preferable that a known substituent is introduced into the compound (C-1) selected from the compounds (C-1) and (C-2) described above and derivatives thereof.
  • the substituent becomes a substituent of the residue of the compound (C), and can provide performances such as various properties, functions and physical properties to the dye derivative of the present invention.
  • the substituent is selected from, for example, the following hydrophilic group group, lipophilic group group, and reactive group group.
  • ⁇ Group of hydrophilic groups Any anionic group selected from a carboxyl group, a sulfonic acid group, a phosphate ester group and a sulfate ester group; -Alkali metal salts, ammonium salts, (mono, di, tri) -alkylamine salts, (mono, di, tri) -alkanolamine salts, (mono, di, tri)-(polyoxy) of these anionic groups A salt of any anionic group selected from (alkylene) oxyalkylamine salts; Any cationic group selected from a tertiary amino group and a quaternary ammonium group; A salt of any one of these cationic groups selected from a halogenate, a sulfonate, and an alkyl carboxylate; Any nonionic group selected from a polyalcohol group and a polyethylene glycol group;
  • ⁇ Group of lipophilic groups Any group selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, and a halogen group ⁇ reactive group group> Any group selected from the group consisting of a glycidyl group, a methylol group, and an alkoxy (carbon number: 1 to 4) methyl group;
  • hydrocarbon compound (C-1) having a methine group (—CH ⁇ ) having an easily replaceable hydrogen group described above is specifically shown below.
  • a phenol compound suitable as a hydrocarbon compound having an easily replaceable hydrogen atom of an aromatic skeleton a reactive phenol compound having an active hydrogen group at the o-position or p-position of a hydroxyl group or an equivalent position thereof is preferable.
  • Specific examples include aromatic hydrocarbons having 6 to 20 carbon atoms having a phenolic hydroxyl group and heterocyclic compounds.
  • known phenol compounds (hydroxybenzenes), naphthols, hydroxycarbazoles and the like having one to a plurality of hydroxyl groups (such as 4) in the molecule are suitable.
  • Particularly preferred phenolic compounds in the present invention include, when reacted with the dye (A) and the aldehyde compound (B), the substituent is at the o-position or p-position of the phenolic hydroxyl group or the equivalent position thereof. Are introduced so as to leave an active hydrogen group. For example, the following are mentioned.
  • Examples of phenols having an alkyl group as a substituent include 2-t-butyl-4-methylphenol, 2-t-butyl-6-methylphenol, 2,3 as amphiphilic nonpolar phenols.
  • the above phenolic hydroxyl group can be subsequently etherified with an alkyl halide or an epoxy compound.
  • the ether group formed at this time include an alkyl ether group, an alkyl (hydroxy) propyl ether group, an alkoxy (hydroxy) propyl ether group, a phenyl ether group, and a phenoxy (hydroxy) propyl ether group.
  • suitable hydrocarbon compounds having easily replaceable hydrogen atoms with an aromatic skeleton other than the above-described phenol compounds include N, N-disubstituted aniline compounds.
  • N, N-dialkylaniline, N, N-dialkanolaniline, or the like are examples of suitable hydrocarbon compounds having easily replaceable hydrogen atoms with an aromatic skeleton other than the above-described phenol compounds.
  • amino compound having a reactive amino group (C-2) Specific examples of the amino compound (C-2) having a reactive amino group used in the present invention that can be suitably used are shown below.
  • the amino acid compound having 1 to 10 carbon atoms include glutamic acid, aspartic acid, taurine, N-methyl taurine and the like.
  • the amino compound having 1 to 20 carbon atoms include N, N-dimethylethylenediamine, N, N-diethyl-1,3-diaminopropane, N, N-diethyl 1,4-diaminopentane, diethanolamine, and diisopropanolamine.
  • aminotriazine compound having 0 to 10 carbon atoms examples include 2-amino-4,6-dihydroxy-s-triazine, 2-amino-4,6-dipropylamino-s-triazine, 2-amino- Examples include 4,6-carboxymethylamino-s-triazine, 2-amino-4,6-dicarboxymethylamino-s-triazine, and the like.
  • Examples of the carbonamide compound having 1 to 20 carbon atoms include acetamide, propioamide, butyramide, octanamide, stearamide, trimellitic acid monoamide, sulfosuccinic acid monoamide, and the like, and nitriles that are amidated when used in sulfuric acid, for example, Examples include acetonitrile, octonitrile, stearonitrile, and benzonitrile.
  • Specific examples of carboimide compounds (excluding phthalimide) suitable for the present invention include trimellitic imide, sulfosuccinimide, o-sulfobenzimide and the like.
  • Examples of the sulfamic acid compound include sulfamic acid.
  • the dye derivative of the present invention is obtained by reacting the water-insoluble dye (A), the aldehyde compound (B) and the compound (C) described above.
  • the reaction medium used in that case will be described.
  • a reaction medium suitable for the present invention is a medium in which the water-insoluble dye (A) is dissolved.
  • the organic pigments and vat dyes which are the preferred colorants (A) of the present invention mentioned above do not dissolve in ordinary organic solvents, so 95% to 100% highly concentrated sulfuric acid, fuming sulfuric acid, polyphosphoric acid, etc. are used. Is done.
  • reaction product obtained from the components (A), (B) and (C) described above is poured into a large amount of water, ice water or ice in accordance with a conventional method from a sulfuric acid solution, etc. What is necessary is just to filter and wash with water. At this time, it is washed with a weakly acidic aqueous hydrochloric acid solution depending on the properties of the pigment derivative.
  • the dye derivative of the present invention has a color tone and lyophilicity depending on the nature of the compound (C) residue bonded to the molecular structure of the water-insoluble dye (A) via an alkylene group and the number of residues to be introduced. Since the properties change, it is preferable to determine the setting and the number of introduced compounds (C) via an alkylene group (for example, a methylene group) so that the target dye derivative is synthesized.
  • the number of bonds (number) of the compound (C) residue is not particularly limited, but is about 1 to 6. When used as a water-soluble dye, it is necessary to be able to bring about water solubility, and it is preferable to introduce approximately 2 or more, preferably 3 or more.
  • the substituent of the compound (C) residue of the pigment derivative is preferably in the form of a salt.
  • the substituent is an anionic group comprising a carboxyl group, a sulfonic acid group, a phosphoric ester group, or a sulfuric ester group, an alkali metal salt such as a sodium salt or a potassium salt of the anionic group; an ammonium salt; (Mono, di, tri) ethylamine salts, (mono, di, tri) alkylamine salts such as propylamine salts; (mono, di, tri) ethanolamine salts, (mono, di, tri) ) (Mono, di, tri) alkanolamine salts such as propanolamine salts; (mono, di, tri)-(polyoxyalkylene) oxyalkylamine salts such as (mono, di, tri) (polyethyleneoxyethyl)
  • the substituent is a cationic group composed of a tertiary amino group or a quaternary ammonium group
  • a halogen salt such as hydrochloride of the cationic group
  • an alkyl such as acetic acid or propionate Carboxylic acid salt
  • It is preferably a hydrophilic group such as a hydroxyalkyl carboxylate such as glycolate or lactate.
  • the alkylene group in which the compound (C) residue formed by the aldehyde compound (B) and the compound (C) is bonded to the molecular structure of the original dye is bonded as a substituent. Configured.
  • the pigment derivative of the present invention has an effect of deepening the original color tone of the water-insoluble pigment (A) (shifting the absorption wavelength to the longer wavelength side).
  • the number of the above-mentioned substituents shifts to greenish blue particularly when it is 2 or more, which is desired in the image recording field such as inkjet printing Cyan to sky blue colors that are characteristic of being obtained.
  • the number of substituents in the present invention means the number of compound (C) residues bonded through an alkylene group.
  • the dye derivative of the present invention when used as a colorant, the dye derivative of the present invention can be used in various fields by diluting it with various dilution media suitable for various applications. Thus, simpler use is possible.
  • the colorant of the present invention is a liquid medium composed of any one of an organic solvent system, an aqueous system, or a water-hydrophilic organic solvent mixed solvent system, or a polymerizable oligomer or polymerized polymer. It is characterized by containing at least one of a polymerizable liquid medium made of a polymerizable monomer or a resin medium made of a synthetic resin.
  • the base color (pigment solution or dispersion) constituting the colorant of the present invention contains the pigment derivative of the present invention and, if necessary, other pigments, oil-soluble dyes or water-soluble dyes as a medium.
  • the above-described liquid medium, polymerizable liquid medium, and resin medium may be used, and if necessary, the dispersion aid may be further used with a polymer system dispersant or a low molecular dispersion aid.
  • the dye derivative of the present invention has the pigment crystal transition inhibition, crystal growth inhibition, and dispersibility. It can also be added and used for the purpose of improving the heat resistance.
  • the pigment derivative of the present invention added to a pigment crude (coarse pigment) or a coarse particle pigment to form a pigment composition is effective for the post-treatment (pigmenting treatment) of the pigment.
  • This dye derivative brings an excellent effect in improving the dispersion performance of the liquid dispersion color of the pigment and improving the storage stability.
  • it is desirable that the pigment is insoluble in an organic solvent medium.
  • an oleophilic group is introduced as a substituent of the aforementioned compound (C) residue, and the oleophilic group is approximately 1 or less, preferably an average number relative to the entire pigment including the pigment derivative. Those into which 0.5 to 0.1 lipophilic groups are introduced are preferably used.
  • the dye derivative of the present invention having the above ionic group, and its It is preferable to use a philic polymer having a counter ionic group as a pigment dispersant.
  • the dye component is contained in a high concentration, and the dye derivative or other dye used in combination is dissolved or finely dispersed in advance. The production of the colorant can be facilitated.
  • the dye derivative-containing composition using the dye derivative of the present invention contains a dye derivative and other dyes as required in accordance with the intended colorant formulation, and an organic solvent, water or water as a medium.
  • -Liquid medium composed of mixed solvent system of hydrophilic organic solvent; Polymerizable liquid medium composed of polymerizable oligomer and polymerizable monomer; Resin medium composed of plasticizer, oligomer and synthetic resin, dispersed as required It can be prepared by containing a polymer system dispersing agent and a low molecular weight dispersing aid as an auxiliary agent.
  • the colorant containing the pigment derivative of the present invention is a dyeing agent, a printing agent, a paint, a printing ink, a stationery, a paint, a resin colorant, and various information technology-related colorants, for example, for color resists used in the production of color filters It can be applied as a colorant, a liquid colorant such as a liquid developer for an electrophotographic printer, or a dry developer for an electrophotographic printer. Then, they are used for known coloring methods such as dyeing, textile printing, painting, printing, writing, drawing, resin coloring, electrophotographic printing, electrostatic printing, and color filter pixel forming methods.
  • the colorant of the present invention contains the pigment derivative of the present invention, and, if necessary, other pigments such as other pigments, oil-soluble dyes, water-soluble dyes, etc. It is prepared by adding one or more materials selected from thermoplastic polymers, reactive polymers, reactive oligomers, polymerizable monomers, crosslinking agents, and the like as the coating film forming material. If necessary, the colorant of the present invention may further include a curing catalyst, a polymerization catalyst, or the like. Alternatively, the above-described dye derivative-containing composition may be used, and the necessary materials described above may be further added to dissolve, mix, It can be prepared by adding necessary processing according to the application such as dispersion.
  • known resin components corresponding to the respective applications are used.
  • known coating film forming materials such as synthetic rubber resin, acrylic resin, vinyl resin, chlorinated rubber resin, alkyd resin, urethane resin, epoxy resin, silicone resin, fluororesin, and ultraviolet curable resin system, electron beam curable Examples include resin-based energy ray-curable coating film forming materials.
  • the coating film forming material may or may not have a reactive group. Examples of the reactive group include a methylol group, an alkylmethylol group, an isocyanate group, a masked isocyanate group, and an epoxy group. Can be mentioned.
  • the material or article colored by the colorant of the present invention is determined by the purpose and application of coloring, and conventionally known materials and articles are targeted.
  • coloring compositions for image recording such as digital laser printers and full-color toners for full-color copiers
  • articles to be colored with the composition include paper, synthetic paper, non-woven paper, and plastic films. It is done.
  • a colorant suitable for the formation method is used, and a known photoresist method, printing method, transfer method, and pasting are performed on the color filter substrate. Pixels are formed by the method.
  • a coloring composition for image display such as a color filter for a liquid crystal display and an advertising display
  • examples of the coloring object of the composition include a glass substrate and a plastic plate substrate.
  • Comparative Production Example 1 Preparation of comparative blue pigment composition
  • ⁇ -type copper phthalocyanine pigment is included as a main component in the same manner as in Production Example 1-3, except that a known monosulfonated copper phthalocyanine is used instead of the blue pigment derivative-1 used in Production Example 1-3.
  • a comparative blue pigment composition was prepared. Hereinafter, this is referred to as “comparative blue pigment composition-1”.
  • Table 2 shows the composition.
  • the mixture was cooled to room temperature, precipitated in approximately 1,000 ml of ice water, filtered, washed with water, and dried. The soluble matter was removed by washing with acetone to obtain trimellitic acid imidomethylated copper phthalocyanine which is a pigment derivative of the present invention.
  • the number of substitution is approximately 3.2.
  • a flavanthrone yellow pigment (CI Pigment Yellow 24) was reacted to obtain a 10% aqueous solution of a sodium salt of trimellitic acid monoamidomethyl derivative.
  • this is referred to as “yellow pigment derivative-1 aqueous solution”.
  • each pigment derivative aqueous solution saponified with sodium hydroxide aqueous solution was acidified with dilute hydrochloric acid aqueous solution to precipitate pigment derivative carboxylic acid and filtered to obtain a mud.
  • a 20% ethanolamine aqueous solution was added thereto for neutralization, and the pH was adjusted to 8. Thereafter, the insoluble matter was filtered off, and water was added to prepare a 10% aqueous solution, thereby obtaining a 10% aqueous solution of an ethanolamine salt of trimellitic acid amidomethyl derivative.
  • blue pigment derivative-5-2 aqueous solution “red pigment derivative-1-2 aqueous solution”
  • yellow pigment derivative-1-2 aqueous solution and “yellow pigment derivative-1-2 aqueous solution”.
  • Example 1 Preparation of dispersion] (1-1) (Preparation of blue pigment dispersion-1) Blue pigment composition-1 (reddish blue pigment composition containing ⁇ -type copper phthalocyanine as a main component) obtained in Production Example 1-3, benzyl methacrylate-methacrylic acid-2-hydroxyethyl methacrylate copolymer ( Molar ratio: 60:20:20, weight average molecular weight 30,000) (hereinafter referred to as “BzMA-MAc-HEMA copolymer”) 30 parts, cyclohexanone 100 parts and propylene glycol monomethyl ether acetate (hereinafter abbreviated as PGMA) ) 60 parts Dispersic-163 (by Big Chemie: solid content 45%) 66.7 parts were premixed with a paint conditioner.
  • Blue pigment composition-1 reddish blue pigment composition containing ⁇ -type copper phthalocyanine as a main component
  • BzMA-MAc-HEMA copolymer benzyl me
  • Example 1-1 (Preparation of Comparative Blue Pigment Dispersion-1) Except for using the comparative blue pigment composition-1 obtained in Comparative Production Example 1 (including a known ⁇ -type copper phthalocyanine pigment using a monosulfonated copper phthalocyanine as a main component), Example 1-1 Similarly, “Comparative Blue Pigment Dispersion-1” was prepared.
  • Example 2 Application to glass substrate
  • (2-1) preparation of blue glass substrate
  • a glass substrate was set on a spin coater, and the blue pigment dispersion liquid-1 obtained in Example 1 was dropped, and spin coating was initially performed at 300 rpm for 5 seconds and then at 1,200 rpm for 5 seconds. Subsequently, prebaking was performed at 90 ° C. for 2 minutes, and further post-baking was performed at 230 ° C. for 30 seconds to prepare a blue coated glass substrate-1.
  • this is referred to as “blue coated glass substrate-1”.
  • the comparative blue coated glass substrate-1 using the comparative blue pigment dispersion-1 having monosulfonated copper phthalocyanine showed a maximum transmission wavelength of 461 nm and a Y value of 17.0.
  • the glass substrate using the pigment derivative of the present invention shows a reddish blue color compared to the glass substrate using the monosulfonated copper phthalocyanine as a comparison, and the maximum transmission wavelength is on the short wavelength side.
  • the dye derivative was more reddish blue.
  • the dye derivative of the present invention has a high Y value.
  • Example 3 Application to color filter
  • 3-1 20 parts of the blue pigment composition-1 obtained in Production Example 1-2, 2 parts of BzMA-MAc-HEMA copolymer, 13.3 parts of Dispersic-163, and 64.7 parts of PGMA was premixed with a paint conditioner and then dispersed with a continuous horizontal medium disperser to obtain a blue pigment dispersion using the dye derivative of the present invention.
  • this is referred to as “blue pigment dispersion-2”.
  • the blue pigment fine dispersion obtained here was excellent in storage stability without thickening at 45 ° C. for 1 week.
  • the composition is shown in Table 5.
  • the glass substrate was set on a spin coater, and the above-described photosensitive red resist ink was first spin-coated at 300 rpm for 5 seconds and then at 1,200 rpm for 5 seconds. Subsequently, prebaking was performed at 80 ° C. for 10 minutes, and a photomask having a mosaic pattern was exposed on the coated surface of the glass substrate with a super high pressure mercury lamp at a light amount of 100 mJ / cm 2 using a proximity exposure machine. Next, development and washing were performed with a dedicated developer and a dedicated rinse to form a red mosaic pattern on the glass substrate.
  • a green mosaic pattern and a blue mosaic pattern were formed by applying and baking according to the above method using the photosensitive green resist ink and the photosensitive blue resist ink in Table 6, and RGB color filters were formed. Obtained.
  • the obtained color filter has excellent spectral curve characteristics, excellent fastness such as light resistance and heat resistance, and excellent light transmission properties, and is excellent as a color filter for liquid crystal color displays. Showed the nature.
  • Example 4 Preparation of electrophotographic developer for digital printing and digital electronic printing
  • 4-1 Preparation of high pigment content resin composition
  • 30 parts of “Blue Dye Derivative-4” obtained in Production Example 4 is a polyester resin of bisphenol A-bis (propylene glycol ether) and terephthalic acid (average molecular weight: about 15,000) (hereinafter simply referred to as a polyester resin).
  • 70 parts and two rolls were kneaded to prepare a blue pigment polyester masterbatch (resin composition containing a high pigment concentration) (hereinafter referred to as a blue masterbatch).
  • Example 5 Printing with water-based printing ink] (5-1) (Preparation of aqueous gravure ink coating agent) 50 parts of polyurethane-based aqueous resin (solid content 30%) containing carboxyl group obtained from carbonate-based polyol and aliphatic isocyanate, 5 parts of water-dispersed wax (solid content 30%), 15 parts of polycarbodiimide-based crosslinking agent, 1 part of a foaming agent and 9 parts of water were blended to prepare a coating vehicle base. 20 parts of each of the blue dye derivative-5 aqueous solution, red pigment derivative-1 aqueous solution, and yellow pigment derivative-1 aqueous solution obtained in Production Example 5 were added as colorants and mixed well to obtain blue, red, and yellow coating agents.
  • Example (5-1) In the same manner as in Example (5-1), the obtained coating agent was used as an aqueous gravure ink, and gravure printing or flexographic printing was performed on the plastic film or sheet. All of the obtained printed materials were beautiful and transparent printed materials excellent in physical properties such as weather resistance, water resistance and durability.
  • Example 6 Preparation, dyeing and painting of colored coating agent
  • (6-1) (Preparation of colored coating agent) Methyl methacrylate-ethyl acrylate-acrylic acid (64: 32: 4) copolymer latex (solid content 40%) 40 parts, mica 3 parts, talc 7 parts, 3% hydroxycellulose aqueous solution 10 parts, propylene glycol 1 part of monoethyl ether, 2 parts of ethylene glycol, 0.5 part of antifoaming agent, 0.5 part of preservative, 10 parts of the polycarbodiimide crosslinking agent used in Example 5 and 6 parts of water were blended to form a coating vehicle base.
  • (6-1) (Preparation of colored coating agent) Methyl methacrylate-ethyl acrylate-acrylic acid (64: 32: 4) copolymer latex (solid content 40%) 40 parts, mica 3 parts, talc 7 parts, 3% hydroxycellulose aqueous solution 10 parts, propylene glycol 1 part of
  • the soluble pigment is excellent in light resistance as compared with the dye, and the color tone also provides a deep color effect depending on the number of substitutions, and particularly the sky blue color from the phthalocyanine pigment is suitable. Can get to.
  • pigment derivatives effective as additives for suppressing pigment crystal transition and crystal growth, and pigments of organic solvent-based pigment dispersion colors A colorant containing a functional additive such as a dispersion aid that improves the dispersibility, decreases the viscosity of the dispersion, improves dispersion stability, long-term storage stability, and the like can be obtained. Since these can be obtained from derivatives based on existing dye skeletons, they can be carried out economically and efficiently.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Optical Filters (AREA)
  • Coloring (AREA)
  • Paints Or Removers (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

La présente invention a pour objet un dérivé de pigment caractérisé en ce qu'il est un dérivé de colorant obtenu par la liaison de la molécule d'un colorant insoluble dans l'eau (A) et du résidu d'un composé (C) l'un à l'autre par un groupe alkylène formé par la réaction du colorant (A) avec un composé aldéhyde (B). Par la sélection appropriée du composé (C) parmi des composés hydrocarbonés (C-1) ayant un groupe méthane (-CH=) avec un groupe hydrogène qui est sensible à une substitution et des composés amino (C-2) ayant un groupe amino réactif, un effet coloré plus intense que la couleur d'un colorant existant est apporté. En outre, par l'utilisation d'un dérivé de pigment efficace en tant qu'additif pour la suppression du transfert cristallin ou de la croissance cristalline d'un pigment et également par l'utilisation du dérivé de colorant, un colorant qui possède l'effet mentionné ci-dessus, et atteint également une diminution de la viscosité d'une dispersion pigmentaire et possède des propriétés améliorées telles qu'une stabilité de dispersion et une stabilité de stockage à long terme est réalisé. Par l'utilisation de ce colorant, un procédé de coloration utile et un article coloré sont obtenus.
PCT/JP2010/065478 2009-09-10 2010-09-09 Dérivé de colorant, colorant, et procédé de coloration Ceased WO2011030810A1 (fr)

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JP2011514930A JP5465718B2 (ja) 2009-09-10 2010-09-09 色素誘導体、着色剤及び着色方法
CN201080040152.4A CN102482513B (zh) 2009-09-10 2010-09-09 色素衍生物、着色剂及着色方法

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TWI458784B (zh) 2014-11-01
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CN102482513A (zh) 2012-05-30
KR20120065389A (ko) 2012-06-20
TW201116592A (en) 2011-05-16
JP5465718B2 (ja) 2014-04-09

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