WO2014050594A1 - Dispersion de pigment, encre, encre pour impression par jet d'encre, et procédé de fabrication de dispersion de pigment - Google Patents

Dispersion de pigment, encre, encre pour impression par jet d'encre, et procédé de fabrication de dispersion de pigment Download PDF

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Publication number
WO2014050594A1
WO2014050594A1 PCT/JP2013/074715 JP2013074715W WO2014050594A1 WO 2014050594 A1 WO2014050594 A1 WO 2014050594A1 JP 2013074715 W JP2013074715 W JP 2013074715W WO 2014050594 A1 WO2014050594 A1 WO 2014050594A1
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Prior art keywords
mass
pigment dispersion
pigment
ink
compound
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PCT/JP2013/074715
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English (en)
Japanese (ja)
Inventor
丈雄 城▲崎▼
龍一 松岡
北田　満
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Dic株式会社
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Priority to JP2014538386A priority Critical patent/JP5733591B2/ja
Publication of WO2014050594A1 publication Critical patent/WO2014050594A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
    • 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
    • C09B67/009—Non common dispersing agents polymeric dispersing agent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/322—Pigment inks
    • C—CHEMISTRY; METALLURGY
    • 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
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium

Definitions

  • the present invention relates to a pigment dispersion that can be used in the production of ink that can be used when printing is performed by various printing methods including the ink-jet printing method.
  • the water-based pigment ink is generally obtained by mixing a pigment dispersion, which is a precursor thereof, with various additives and diluting with an aqueous medium.
  • a pigment dispersion which is a precursor thereof
  • the pigment ink obtained using the pigment dispersion as the precursor include, for example, a pigment, 5 to 30 parts by weight of a (meth) acrylic acid alkyl ester compound having a long-chain alkyl group having 8 to 20 carbon atoms, ⁇ , 5 to 30 parts by weight of ⁇ -monoethylenically unsaturated carboxylic acid monomer and 40 to 90 parts by weight of other copolymerizable radical polymerizable monomer (however, the total of the above monomer components is 100 parts by weight)
  • the ratio of the acrylic resin and the compound having an ether structure having a specific structure is mainly comprised of an acrylic resin obtained by copolymerization of the compound, a compound having an ether structure having a specific structure, a basic compound and an a
  • Resin / compound having ether structure of specific structure] 20/80 to 80/20 (weight ratio), and 100 parts by weight of pigment and the acrylic resin and the compound
  • An ink composition for ink-jet recording which contains 8 to 300 parts by weight of the total amount of compounds having a specific ether structure (see, for example, Patent Document 1).
  • the ink composition causes aggregation of pigment particles due to the influence of the organic solvent used in manufacturing the ink composition
  • the sharpness of the printed image is reduced.
  • it may cause sedimentation of the pigment or clogging of the ink discharge nozzle due to aggregation of the pigment particles, and the dispersion stability and discharge stability of the pigment dispersion and ink. In some cases, it was not possible to improve the performance.
  • the problem to be solved by the present invention is to provide a pigment dispersion which is excellent in pigment dispersion stability and ink ejection stability and which is used for producing an ink capable of forming a clear printed image.
  • the present inventors have found that the above problems can be solved by using a pigment dispersant containing a compound having a hydantoin structure, and have completed the present invention.
  • the present invention relates to a pigment dispersion characterized by containing a compound (A) having a hydantoin structure and a pigment, an ink containing the pigment dispersion, and an ink for inkjet printing.
  • the pigment dispersion of the present invention can produce an ink excellent in pigment dispersion stability and capable of forming a clear printed image, particularly an ink for inkjet printing.
  • the ink for inkjet printing obtained using the pigment dispersion can maintain excellent ejection stability from the ink ejection nozzle for a long period of time.
  • the pigment dispersion of the present invention is characterized by containing a compound (A) having a hydantoin structure and a pigment.
  • the hydantoin structure possessed by the compound (A) specifically refers to a cyclic structure represented by the following general formula (1).
  • R 1 and R 2 in General Formula (1) each independently represent a hydrogen atom or an alkyl group.
  • R 1 and R 2 in the general formula (1) include a hydrogen atom or an alkyl group such as a methyl group or an ethyl group. Among them, a methyl group or an ethyl group is preferable.
  • the hydantoin structure is an essential structure for producing an ink capable of improving the dispersion stability of the pigment and forming a clear printed image.
  • the hydantoin structure is an essential structure for producing ink for ink jet printing excellent in ink ejection stability.
  • the structure represented by the following general formula (1-1) is preferable because the hydantoin structure can be easily introduced into the compound (A).
  • R 1 and R 2 in the general formula (1-1) each independently represent a hydrogen atom or an alkyl group, and R 3 and R 4 each independently represent an alkylene group.
  • R 1 and R 2 in the general formula (1-1) include a hydrogen atom or an alkyl group such as a methyl group or an ethyl group. Among them, a methyl group or an ethyl group is preferable.
  • R 3 and R 4 in the general formula (1-1) include alkylene groups such as a methylene group, an ethylene group, a propylene group, and a butylene group, and a methylene group and an ethylene group are preferable.
  • the hydantoin structure represented by the general formula (1) is preferably present in the range of 1 to 30% by mass in the compound (A), and preferably present in the range of 3 to 20% by mass. It is more preferable for producing an ink having excellent stability and, as a result, further excellent ink ejection stability and storage stability.
  • the hydantoin structure represented by the general formula (1) in the general formula (1-1) is 1 to 30 masses in the compound (A). %, Preferably 3 to 20% by mass.
  • the compound (A) having a hydantoin structure has a weight average molecular weight in the range of 5,000 to 100,000 in order to further improve the dispersion stability of the pigment, and particularly to improve the ejection stability of the ink. It is preferable to use those having a weight average molecular weight in the range of 10,000 to 50,000.
  • the said compound (A) uses what has hydrophilic groups, such as anionic group, a cationic group, a nonionic group, from a viewpoint which provides the outstanding dispersion stability in an aqueous medium (B), for example. It is preferable to use a compound having one or both of an anionic group and a cationic group.
  • a carboxyl group, a carboxylate group, a sulfonic acid group, a sulfonate group, and the like can be used.
  • a part or all of the carboxyl group and the sulfonic acid group are basic compounds. It is preferable to use a carboxylate group or a sulfonate group neutralized by the above in order to impart good water dispersion stability.
  • a tertiary amino group etc. can be used, for example.
  • examples of the nonionic group include a polyoxyethylene structure.
  • the hydrophilic group is preferably present in the compound (A) in the range of 15 to 2,000 mmol / kg, and more preferably in the range of 500 to 1,000 mmol / kg. And more preferable for obtaining a pigment dispersion having ejection stability.
  • the compound (A) it is preferable to use a compound having a urea bond in the range of 0 to 2% by mass in the compound (A) in order to further improve the dispersion stability of the pigment.
  • the use of a compound having a primary amino group in the range of 0 to 5% by mass in the compound (A) prevents aggregation of pigment particles and provides a clear printed image.
  • polyurethane (A-1) for example, polyurethane (A-1), vinyl resin such as acrylic resin, polyester resin and the like can be used.
  • polyurethane (A-1) or vinyl resin (A-2). ) Is more preferable.
  • the polyurethane (A-1) can be produced, for example, by reacting a polyol (a1) containing a polyol having a hydantoin structure, a polyisocyanate (a2), and, if necessary, a chain extender. .
  • polyol having the hydantoin structure those having the structure represented by the general formula (1) can be used.
  • a polyol represented by the following general formula (2) can be preferably used.
  • R 1 and R 2 in General Formula (2) each independently represent a hydrogen atom or an alkyl group, and R 3 and R 4 each independently represent an alkylene group.
  • R 1 and R 2 in the general formula (2) include a hydrogen atom or an alkyl group such as a methyl group or an ethyl group. Among them, a methyl group or an ethyl group is preferable.
  • alkylene groups such as a methylene group, ethylene group, a propylene group, or a butylene group, are mentioned, A methylene group and ethylene group are preferable.
  • the polyol represented by the general formula (2) includes 1,3-bis (hydrazinocarbonoethyl) -5-isopropylhydantoin), 1,3-bis (hydroxymethyl) -5,5.
  • -Dimethylimidazolidine-2,4-dione 1,3-bis (2-hydroxyethyl) -5,5 dimethylimidazolidine-2,4-dione, etc. are preferably used, and 1,3-bis (2 More preferably, -hydroxyethyl) -5,5 dimethylimidazolidine-2,4-dione is used.
  • polyol (a1) other polyols can be used as needed in addition to the polyol having the hydantoin structure.
  • a polyol having a hydrophilic group can be used from the viewpoint of imparting good water dispersion stability of the polyurethane (A-1).
  • polyol having a hydrophilic group for example, a polyol having an anionic group, a polyol having a cationic group, and a polyol having a nonionic group can be used, and among them, a polyol or a cation having an anionic group. It is preferable to use a polyol having a functional group.
  • polyol having an anionic group for example, a polyol having a carboxyl group or a polyol having a sulfonic acid group can be used.
  • polyol having a carboxyl group examples include 2,2-dimethylolpropionic acid, 2,2-dimethylolbutanoic acid, 2,2-dimethylolbutyric acid, 2,2-dimethylolvaleric acid, and the like. Of these, 2,2-dimethylolpropionic acid is preferably used.
  • polyester polyol which has a carboxyl group obtained by making the polyol which has the said carboxyl group react with various polycarboxylic acids can also be used.
  • polyol having a sulfonic acid group examples include dicarboxylic acids such as 5-sulfoisophthalic acid, sulfoterephthalic acid, 4-sulfophthalic acid, 5- (4-sulfophenoxy) isophthalic acid, and salts thereof,
  • dicarboxylic acids such as 5-sulfoisophthalic acid, sulfoterephthalic acid, 4-sulfophthalic acid, 5- (4-sulfophenoxy) isophthalic acid, and salts thereof
  • a polyester polyol obtained by reacting with a molecular weight polyol can be used.
  • the polyol having a carboxyl group or the polyol having a sulfonic acid group is preferably used in the range where the acid value of the polyurethane (A-1) is from 10 to 70, and preferably from 10 to 60. More preferably, it is particularly preferably used in the range of 30-50.
  • the acid value referred to in the present invention is a theoretical value calculated based on the amount of a compound having an acid group such as a polyol having a carboxyl group used in the production of the polyurethane (A-1).
  • the anionic group is preferably partially or completely neutralized with a basic compound or the like in order to develop good water dispersibility.
  • Examples of basic compounds that can be used when neutralizing the anionic group include organic amines having a boiling point of 200 ° C. or higher, such as ammonia, triethylamine, morpholine, monoethanolamine, diethylethanolamine, sodium hydroxide, A metal hydroxide containing potassium hydroxide, lithium hydroxide or the like can be used.
  • polyol having a cationic group for example, a polyol having a tertiary amino group can be used. Specifically, N-methyl-diethanolamine and a compound having two epoxies in one molecule can be used. A polyol obtained by reacting with a secondary amine can be used.
  • the cationic group is preferably partially or completely neutralized with an acidic compound such as formic acid, acetic acid, propionic acid, succinic acid, glutaric acid, tartaric acid, and adipic acid.
  • an acidic compound such as formic acid, acetic acid, propionic acid, succinic acid, glutaric acid, tartaric acid, and adipic acid.
  • the tertiary amino group that can be used as the cationic group is preferably partially or entirely quaternized.
  • the quaternizing agent for example, dimethyl sulfate, diethyl sulfate, methyl chloride, ethyl chloride and the like can be used, and dimethyl sulfate is preferably used.
  • polyol having a nonionic group polyalkylene glycol having a structural unit derived from ethylene oxide can be used.
  • the polyol having a hydrophilic group is preferably used in the range of 1 to 45% by mass with respect to the total mass of raw materials used for the production of the polyurethane (A-1).
  • polyether polyols for example, polyether polyols, polyester polyols, polyester ether polyols, polycarbonate polyols and the like can be used other than those described above.
  • polyether polyols it is preferable to use a polyether polyol in order to further improve the dispersion stability of the pigment.
  • polyether polyol for example, one obtained by addition polymerization of alkylene oxide using one or more compounds having two or more active hydrogen atoms as an initiator can be used.
  • the initiator examples include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, trimethylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, glycerin, trimethylolethane. Trimethylolpropane and the like can be used.
  • alkylene oxide for example, ethylene oxide, propylene oxide, butylene oxide, styrene oxide, epichlorohydrin, tetrahydrofuran and the like can be used.
  • polyoxytetramethylene glycol, polypropylene glycol, or polyethylene glycol as the polyether polyol in order to improve the ink ejection stability.
  • polyether polyol having a number average molecular weight of 1,000 to 3,000 in order to obtain a printed material that suppresses the tackiness of the printing surface and has excellent water resistance.
  • polyester polyol examples include a ring-opening polymerization reaction of a cyclic ester compound such as an aliphatic polyester polyol, an aromatic polyester polyol, or ⁇ -caprolactone obtained by esterifying a low molecular weight polyol and a polycarboxylic acid. Polyesters obtained by the above, copolymerized polyesters thereof, and the like can be used.
  • the low molecular weight polyol for example, ethylene glycol, propylene glycol and the like can be used.
  • polycarboxylic acid examples include succinic acid, adipic acid, sebacic acid, dodecanedicarboxylic acid, terephthalic acid, isophthalic acid, phthalic acid, and anhydrides or ester-forming derivatives thereof.
  • polyester ether polyol for example, a reaction product of a polyether polyol obtained by adding the alkylene oxide to the initiator and a polycarboxylic acid can be used.
  • the initiator and the alkylene oxide the same ones exemplified as those usable when the polyether polyol is produced can be used.
  • said polycarboxylic acid the thing similar to what was illustrated as what can be used when manufacturing the said polyester polyol can be used.
  • polycarbonate polyol for example, those obtained by reacting a carbonic acid ester with a polyol, or those obtained by reacting phosgene with bisphenol A or the like can be used.
  • carbonate ester methyl carbonate, dimethyl carbonate, ethyl carbonate, diethyl carbonate, cyclocarbonate, diphenyl carbonate and the like can be used.
  • polyol that can react with the carbonate ester examples include ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, dipropylene glycol, 1,4-butanediol, 1,3 -Butanediol, 1,2-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,5-hexanediol, 2,5-hexanediol, 1,6-hexanediol, 1,7- Heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, 3-methyl-1,5-pentanediol, 2 -Ethyl-1,3-hexanediol, 2-methyl
  • polyisocyanate (a2) examples include aromatics such as 4,4′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, carbodiimide-modified diphenylmethane diisocyanate, crude diphenylmethane diisocyanate, phenylene diisocyanate, tolylene diisocyanate, and naphthalene diisocyanate.
  • aromatics such as 4,4′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, carbodiimide-modified diphenylmethane diisocyanate, crude diphenylmethane diisocyanate, phenylene diisocyanate, tolylene diisocyanate, and naphthalene diisocyanate.
  • Polyisocyanates such as hexamethylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, or polyisocyanates having an aliphatic cyclic structure thing It can be.
  • a polyisocyanate having an aliphatic cyclic structure is preferably used. Preference is given to using isocyanates.
  • the polyurethane (A-1) is obtained by, for example, reacting a polyol (a1) containing a polyol having a hydantoin structure with a polyisocyanate (a2) in the presence or absence of a solvent, and removing the solvent as necessary. Can be manufactured.
  • the equivalent ratio of the isocyanate group of the polyisocyanate (a2) to the hydroxyl group of the polyol (a1) is 0.8-2. 5 is preferable, and 1 to 1.5 is more preferable.
  • reaction of the polyol (a1) and the polyisocyanate (a2) is preferably performed in the range of about 20 ° C. to 120 ° C. for about 30 minutes to 24 hours.
  • Solvents usable in the reaction of the polyol (a1) and the polyisocyanate (a2) include, for example, ketone compounds such as acetone and methyl ethyl ketone; ether compounds such as tetrahydrofuran and dioxane; acetate esters such as ethyl acetate and butyl acetate.
  • ketone compounds such as acetone and methyl ethyl ketone
  • ether compounds such as tetrahydrofuran and dioxane
  • acetate esters such as ethyl acetate and butyl acetate.
  • Nitrile compounds such as acetonitrile
  • amide compounds such as dimethylformamide and N-methylpyrrolidone can be used alone or in combination of two or more.
  • a hydantoin structure In order to introduce a hydantoin structure into the polyurethane (A-1), the polyol having the above hydantoin structure is used. After the polyisocyanate (a2) is excessively used to produce a polyurethane having an isocyanate, the following general structure is used. A hydantoin structure may be introduced into the polyurethane (A-1) by reacting the monool represented by the formula (3).
  • R 1 and R 2 in General Formula (3) each independently represent a hydrogen atom or an alkyl group, and R 3 represents an alkylene group.
  • R 1 and R 2 in the general formula (3) include a hydrogen atom or an alkyl group such as a methyl group or an ethyl group, and a methyl group or an ethyl group is preferable.
  • Examples of the monool include 1-hydroxymethyl-5,5-dimethylhydantoin.
  • a chain extender can be used as necessary.
  • polyamine or hydrazine it is preferable to use polyamine or hydrazine as a chain extender.
  • chain extender examples include ethylenediamine, 1,2-propanediamine, 1,6-hexamethylenediamine, piperazine, 2,5-dimethylpiperazine, isophoronediamine, 4,4′-dicyclohexylmethanediamine, 3,3.
  • Diamine compounds such as' -dimethyl-4,4'-dicyclohexylmethanediamine and 1,4-cyclohexanediamine; N-hydroxymethylaminoethylamine, N-hydroxyethylaminoethylamine, N-hydroxypropylaminopropylamine, N-ethylamino Diamine compounds containing one primary amino group and one secondary amino group such as ethylamine and N-methylaminopropylamine; polyamine compounds such as diethylenetriamine, dipropylenetriamine and triethylenetetramine; Hydrazine compounds such as drazine, N, N′-dimethylhydrazine, 1,6-hexamethylenebishydrazine; dihydrazide compounds such as succinic acid dihydrazide, adipic acid dihydrazide, glutaric acid dihydrazide, sebacic acid dihydrazide, isophthalic acid dihydrazide; ⁇ -semicarbazide Semi
  • the chain extender is preferably used in the range where the equivalent ratio of the amino group it has and the isocyanate group it has is 1.9 or less (equivalent ratio). More preferably, it is used in the range of 5 to 1.5 (equivalent ratio).
  • the pigment dispersion of the present invention can be produced, for example, by kneading a compound (A) such as polyurethane (A-1) obtained by the above method with a pigment or the like. Moreover, you may mix the said kneaded material and an aqueous medium (B) as needed.
  • A such as polyurethane (A-1) obtained by the above method
  • B aqueous medium
  • examples of the aqueous medium (B) include water, organic solvents miscible with water, and mixtures thereof.
  • the organic solvent miscible with water include alcohol compounds such as methanol, ethanol, n-propanol and isopropanol; ketone compounds such as acetone and methyl ethyl ketone; polyalkylene glycol compounds such as ethylene glycol, diethylene glycol and propylene glycol; And alkyl ether compounds such as N-methyl-2-pyrrolidone and the like.
  • only water may be used, a mixture of water and an organic solvent miscible with water may be used, or only an organic solvent miscible with water may be used. From the viewpoint of safety and load on the environment, water alone or a mixture of water and an organic solvent miscible with water is preferable, and only water is particularly preferable.
  • vinyl resin (A-2) that can be used for the compound (A) those obtained by polymerizing a vinyl monomer mixture containing a vinyl monomer having a hydantoin structure can be used. .
  • Examples of the vinyl monomer having a hydantoin structure include 1-allylhydantoin, 3- (3-chlorophenyl) -5-methyl-5- (allyloxy) hydantoin, and 3- (3-chlorophenyl) -5-phenyl- 5- (allyloxy) hydantoin, 3-allyl-5,5-dimethylhydantoin, 1-benzyl-3-phenyl-5-allylhydantoin, 3-phenyl-5-allylhydantoin, 3′-allylspiro [tetralin-2,5 '-Hydantoin], 1-methyl-3-allyl-5-[(E) -benzylidene] thiohydantoin, 1-allyl-3-phenyl-5- [1- [2- (methoxycarbonyl) hydrazono] ethyl] hydantoin Etc., and 1-allylhydantoin is preferably used.
  • the vinyl monomer having a hydantoin structure is preferably used in the range of 1 to 30% by mass in the total amount of the vinyl monomer mixture.
  • the hydantoin structure possessed by the vinyl resin (A-2) is preferably a structure derived from the 1-allyl hydantoin, and specifically, one nitrogen in the structure represented by the general formula (1).
  • a structure represented by the following general formula (1-2) in which an atom is bonded to a hydrogen atom is preferable.
  • R 1 and R 2 in the general formula (1-2) each independently represent a hydrogen atom or an alkyl group.
  • R 1 and R 2 in the general formula (1-2) include a hydrogen atom or an alkyl group such as a methyl group or an ethyl group, and among them, a hydrogen atom is preferable.
  • the hydantoin structure represented by the general formula (1-2) is also preferably present in the range of 1 to 30% by mass in the compound (A), and preferably present in the range of 3 to 20% by mass.
  • the dispersion stability of the pigment is excellent, and as a result, it is more preferable for producing an ink having further excellent ink ejection stability and storage stability.
  • vinyl resin (A-2) when the vinyl resin (A-2) is produced, other vinyl monomers can be used as necessary in addition to the vinyl monomer having a hydantoin structure.
  • vinyl monomers examples include vinyl monomers having an acid group such as (meth) acrylic acid, allyl sulfonic acid, sulfopropyl (meth) acrylate, (meth) acryloyloxynaphthalene sulfonic acid, Amide groups such as (meth) acrylamide, diethyl (meth) acrylamide, N-vinylpyrrolidone, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N, N'-methylenebis (meth) acrylamide, etc.
  • an acid group such as (meth) acrylic acid, allyl sulfonic acid, sulfopropyl (meth) acrylate, (meth) acryloyloxynaphthalene sulfonic acid
  • Amide groups such as (meth) acrylamide, diethyl (meth) acrylamide, N-vinylpyrrolidone, N
  • Vinyl monomer having, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate, isobutyl (meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl ( (Meth) acrylate, n-octyl (Meth) acrylate, isooctyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, n-decyl (meth) acrylate, isodecyl (meth) acrylate, n-undecyl (meth) acrylate, n-dodecyl ( (Meth) acrylate, n-tridecyl (meth) acrylate, n-tetradecyl (meth) acrylate
  • the other vinyl monomers are preferably used in the range of 80 to 99% by mass in the total amount of the vinyl monomer mixture used for producing the vinyl resin (A-2).
  • the vinyl resin (A-2) can be produced, for example, by radical polymerization of a mixture of various vinyl monomers in the presence of a polymerization initiator and an aqueous medium.
  • the compound (A) is preferably included in the range of 5 to 200 parts by mass with respect to 100 parts by mass of the pigment described later, and included in the range of 20 to 100 parts by mass, the dispersion stability of the pigment and the ink This is more preferable for further improving the discharge performance.
  • the pigment known and commonly used inorganic pigments and organic pigments can be used.
  • the inorganic pigment include titanium oxide, antimony red, bengara, cadmium red, cadmium yellow, cobalt blue, bitumen, ultramarine, carbon black, and graphite.
  • organic pigments examples include quinacridone pigments, quinacridone quinone pigments, dioxazine pigments, phthalocyanine pigments, anthrapyrimidine pigments, ansanthrone pigments, indanthrone pigments, flavanthrone pigments, perylene pigments, Organic pigments such as diketopyrrolopyrrole pigments, perinone pigments, quinophthalone pigments, anthraquinone pigments, thioindigo pigments, benzimidazolone pigments, and azo pigments can be used.
  • examples of the black pigment include carbon black (CI pigment black 7) such as furnace black, lamp black, acetylene black, and channel black; copper oxide, iron oxide (C.I. Pigment black 11), metal oxides such as titanium oxide; aniline black (CI pigment black 1) and the like can be used.
  • color pigments include C.I. I. Pigment yellow 1, C.I. I. Pigment yellow 3, C.I. I. Pigment yellow 74, C.I. I. Pigment yellow 97, C.I. I. Pigment yellow, C.I. I. Pigment Yellow 154, monoazo pigments such as C.I. I. Pigment yellow 12, C.I. I. Pigment yellow 13, C.I. I. Pigment yellow 14, C.I. I. Pigment yellow 17, C.I. I. Pigment yellow 81, C.I. I. Pigment yellow 83, C.I. I. Pigment red 38, C.I. I. Disazo pigments such as C.I. Pigment Orange 13; I.
  • Pigment red 202 C.I. I. Quinacridone pigments such as CI Pigment Red 282 and solid solution pigments thereof; I. Pigment red 254, C.I. I. Pigment red 255, C.I. I. Pigment red 264, C.I. I. Pigment red 270, C.I. I. Diketopyrrolopyrrole pigments such as CI Pigment Red 272, solid solutions of quinacridone pigments and diketopyrrolopyrrole pigments, and the like can be used.
  • These pigments can be used in combination of two or more. These pigments may be surface-treated and have a self-dispersing ability with respect to the aqueous medium (B).
  • Examples of the method of kneading the compound (A) and the pigment include, for example, (i) a method of kneading the compound (A) and the pigment under a high shear force using a two-roll or a mixer, ii) The compound (A) and the pigment are mixed using a dispersing device such as a Henschel mixer, a pressure kneader, or a planetary mixer, and then the solubility of the compound (A) is controlled to control the compound (A). And the like, and a method of mixing them using a dispersing device.
  • a dispersing device such as a Henschel mixer, a pressure kneader, or a planetary mixer
  • the method of kneading by the method (i) is preferable for producing a pigment dispersion having further excellent pigment dispersion stability because the pigment can be finely pulverized.
  • the pigment is preferably contained in the pigment dispersion of the present invention in the range of 5 to 50% by mass, and more preferably in the range of 5 to 30% by mass.
  • the solid content concentration of the kneaded product is preferably 55 to 90% by mass. Thereby, sufficient shearing force can be applied to the compound (A) and the pigment, and a kneaded product in which the pigment is uniformly dispersed can be obtained.
  • a solid content concentration of the kneaded product can be adjusted using a solvent such as polypropylene glycol, a wetting agent, or the like as necessary.
  • the kneading apparatus used in the kneading step may be any kneading apparatus that can generate a high shearing force with respect to a kneaded product having a high solid content ratio, and can be selected from known kneading apparatuses.
  • a kneading apparatus having a stirring tank and stirring blades and capable of sealing the stirring tank rather than using an open kneader having no stirring tank such as a two-roll. It is preferable to use a kneading apparatus having a stirring tank and stirring blades.
  • the kneading apparatus having such a configuration
  • polypropylene glycol, a wetting agent, moisture and the like are not volatilized during kneading, and kneading of a kneaded material having a certain solid content ratio can be continued, thereby reducing coarse particles. It is effective.
  • the kneaded material that is solid at room temperature after kneading can be directly diluted with the aqueous medium (B) to shift to a step of producing a pigment dispersion.
  • kneading is preferably performed in a state where the pigment concentration and the solid content concentration of the pigment and the compound (A) are high, so that the viscosity of the kneaded material varies in a wide range depending on the kneaded state of the kneaded material.
  • the planetary mixer can be kneaded in a wide range of viscosity compared to a two-roller, etc., and further can be added with an aqueous medium (B) and distilled off under reduced pressure. It is easy to adjust the load shear force.
  • a kneader having a stirring tank as described above A method in which a solid kneaded material is produced using, then the aqueous medium (B) is added to and mixed in the stirring tank, and if necessary, stirred to dilute directly.
  • the pigment dispersion can also be produced by a method in which the kneaded product and the aqueous medium (B) are mixed and stirred as necessary using another stirrer equipped with a stirring blade.
  • the aqueous medium (B) may be mixed in a necessary amount with respect to the kneaded product.
  • the aqueous medium (B) is preferably mixed continuously or intermittently. It is preferable because the dilution is efficiently performed and the pigment dispersion of the present invention can be produced in a shorter time.
  • the pigment dispersion obtained by the above method may be subjected to a dispersion treatment using a disperser as necessary.
  • the disperser for carrying out the dispersion treatment known and commonly used equipment can be used, for example, an ultrasonic homogenizer, a high-pressure homogenizer, a paint shaker, a ball mill, a roll mill, a sand mill, a sand grinder, a dyno mill, a dispar mat, a nano mill, an SC mill, Nanomizer etc. can be mentioned, One of these may be used independently and may be used in combination of 2 or more types of apparatuses.
  • the disperser and the disperser are devices that are used exclusively for the dispersion process, and do not include general-purpose mixers and stirrers that are widely used for normal mixing and stirring. And
  • pigment dispersion In addition to the pigment, other additives can be used as necessary as the pigment dispersion.
  • a polymer dispersant or a wetting agent can be used as the additive.
  • an acrylic resin or a styrene-acrylic resin can be used, and any of a random type, a block type, and a graft type can be used.
  • acrylic resin for example, those obtained by polymerizing a (meth) acrylic monomer containing acrylic acid or methacrylic acid can be used.
  • styrene-acrylic resin those obtained by polymerizing the (meth) acrylic monomer and styrene as described above can be used.
  • the acrylic resin and styrene-acrylic resin can be produced by polymerizing a monomer having a polymerizable unsaturated double bond by, for example, a solution polymerization method or a suspension polymerization method.
  • Examples of the monomer having a polymerizable unsaturated double bond include styrene, ⁇ -styrene, ⁇ -styrene, 2,4-dimethylstyrene, ⁇ -ethylstyrene, ⁇ -butylstyrene, ⁇ -hexylstyrene, Chlorostyrene, bromostyrene, nitrostyrene, methoxystyrene, vinyltoluene, (meth) acrylic acid, methyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, sec -Butyl (meth) acrylate, rt-butyl (meth) acrylate, 2-ethylbutyl (meth) acrylate, 1,3-dimethylbutyl (meth) acrylate, hexy
  • a basic compound may be used to neutralize acid groups such as carboxyl groups of the polymer dispersant.
  • polymer dispersant those having a weight average molecular weight in the range of 1,000 to 50,000 are preferably used, and those having a weight average molecular weight of 1,000 to 20,000 are preferably used. More preferred.
  • polymer dispersant one having an acid value of 100 to 500 is preferably used, and one having an acid value of 100 to 200 is more preferably used.
  • wetting agent examples include alcohol solvents, ketone solvents, ether solvents, aromatic hydrocarbon solvents, aliphatic hydrocarbon solvents, halogens, and the like. Aliphatic hydrocarbon solvents are preferred, and glycol solvents are particularly preferred.
  • glycerin polyoxyalkylene adduct of glycerin, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,3-propanediol, 1,4-butanediol, , 5-pentanediol, 1,6-hexanediol, 1,2,6-hexanetriol, trimethylolpropane, pentaerythritol and other polyol compounds, diethylene glycol monobutyl ether, tetraethylene glycol monomethyl ether, propylene glycol monoethyl ether, etc.
  • Polyhydric alcohol alkyl ether compound ethylene glycol monophenyl ether, ethylene glycol monobenzyl ether
  • Polyhydric alcohol aryl ether compounds and polyhydric alcohol aralkyl ether compounds lactam compounds such as 2-pyrrolidone, N-methyl-2-pyrrolidone, and ⁇ -caprolactam, 1,3-dimethylimidazolidinone, and the like can be used. .
  • the alcohol solvent examples include methanol, ethanol, isopropanol, n -butanol, tertiary tert-butanol, isobutanol, diacetone alcohol, and the like.
  • the ketone solvent acetone, methyl ethyl ketone, diethyl ketone, methyl isobutyl ketone, or the like can be used.
  • ether solvent dibutyl ether, tetrahydrofuran, dioxane or the like can be used.
  • Benzene, toluene or the like can be used as the aromatic hydrocarbon solvent.
  • aliphatic hydrocarbon solvent heptane, hexane, cyclohexane or the like can be used.
  • halogenated aliphatic hydrocarbon solvent methylene chloride, 1,1,1-trichloroethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like can be used.
  • diethylene glycol or triethylene glycol glycol as the wetting agent.
  • the wetting agent in the pigment in the range of 20 to 50% by mass because the effect of reducing the coarse particles of the pigment is obtained.
  • the pigment dispersion of the present invention obtained by the above method can be suitably used as a precursor when producing various inks.
  • various inks can be produced by mixing the pigment dispersion, the aqueous medium (B), and a binder resin as necessary.
  • the pigment dispersion, the aqueous medium (B), and, if necessary, a binder resin such as polyurethane are collectively mixed using various dispersing devices, and (2) the above-mentioned
  • the pigment dispersion and the aqueous medium (B) are mixed using various dispersing devices, and then the mixture, the binder resin and the additive are further mixed using various dispersing devices.
  • Ink can be prepared.
  • an ultrasonic homogenizer for example, an ultrasonic homogenizer, a high-pressure homogenizer, a paint shaker, a ball mill, a roll mill, a sand mill, a sand grinder, a dyno mill, a disperse mat, an SC mill, a nanomizer, or the like may be used alone or in combination of two or more. Can do.
  • binder resin that can be used when manufacturing the ink
  • urethane resin or acrylic resin can be used as the binder resin that can be used when manufacturing the ink.
  • the binder resin is preferably used in the range of 0.1 to 5% by mass in the total amount of the ink.
  • additives examples include viscosity modifiers, wetting agents, antifoaming agents, surfactants, preservatives, penetrating agents, pH adjusting agents, chelating agents, and plasticizers. UV absorbers, antioxidants, and the like can be used.
  • the coarse particles having a particle diameter of approximately 250 nm or more may exist.
  • the coarse particles may cause clogging of printer nozzles and the like, and may deteriorate ink discharge characteristics. Therefore, the coarse particles may be coarsened by a method such as centrifugation or filtration after the preparation of the aqueous dispersion of the pigment or after the preparation of the ink. It is preferred to remove the particles.
  • the ink obtained above preferably has a volume average particle diameter of 200 nm or less, and particularly in the case of forming a higher gloss image such as photographic image quality, it is in the range of 80 to 150 nm. Is more preferable.
  • the total amount of the compound (A) such as polyurethane (A-1) is 0.2 to 10% by mass
  • the aqueous medium (B) is 50 to 95% by mass
  • the pigment is 0%. It is preferably contained in the range of 5 to 15% by mass.
  • the ink of the present invention obtained by the above method can be used exclusively when printing by an ink jet printing method using an ink jet printer, for example, ink jet printing on a substrate such as paper, plastic film, metal film or sheet.
  • Can be used for The ink jet printing method is not particularly limited, but a known method such as a continuous jet type (charge control type, spray type, etc.) or an on-demand type (piezo type, thermal type, electrostatic suction type, etc.) should be applied. Can do.
  • Example 1 In a nitrogen-substituted container equipped with a thermometer, a nitrogen gas inlet tube, and a stirrer, 412 parts by mass of polyoxypropylene glycol (number average molecular weight 2000), 120 parts by mass of 2,2-dimethylolpropionic acid and isophorone diisocyanate 357 Part by mass is reacted for 10 hours at 80 ° C. in the presence of 300 parts by mass of methyl ethyl ketone, which is an organic solvent, and then 1,3-bis (2-hydroxyethyl) -5,5 dimethylimidazolidine-2,4-dione is added.
  • polyoxypropylene glycol number average molecular weight 2000
  • 2,2-dimethylolpropionic acid and isophorone diisocyanate 357 Part by mass is reacted for 10 hours at 80 ° C. in the presence of 300 parts by mass of methyl ethyl ketone, which is an organic solvent, and then 1,3-bis (2-
  • Hydantoin in which R 1 and R 2 in the general formula (1-1) are methyl groups and R 3 and R 4 are ethylene groups by supplying and reacting 100 parts by mass and then reacting 11 parts by mass of butanol An organic solvent solution of polyurethane (I) having a structure was obtained.
  • the mixture is stirred with a dispersion stirrer to obtain a precursor of a pigment dispersion (dispersion before dispersion treatment).
  • the precursor of the pigment dispersion was passed through a continuous centrifuge (Kokusan Co., Ltd., Sakai H-600S, 2 L capacity) and centrifuged at a centrifugal force of 18900 G and a residence time of 10 minutes.
  • a pigment dispersion (I-2) was obtained by performing filtration through a 5 ⁇ m filter.
  • the pigment concentration of this pigment dispersion (I-2) was 14.5% by mass.
  • Pigment dispersion (I-2) pigment concentration 14.5% by mass
  • 28 g ⁇ 2-Pyrrolidinone pigment concentration 14.5% by mass
  • 8g ⁇ Triethylene glycol monobutyl ether 8g ⁇ Glycerin
  • 3g ⁇ Surfactant Surfinol 440, manufactured by Air Products
  • 0.5 g ⁇ Ion exchange water 52.5 g
  • Example 2 In a nitrogen-substituted container equipped with a thermometer, a nitrogen gas inlet tube, and a stirrer, 800 parts by mass of methyl ethyl ketone was charged, and then 500 parts by mass of methyl methacrylate, 77 parts by mass of methacrylic acid, 323 parts by mass of styrene, 1-allyl. A monomer liquid consisting of 100 parts by weight of hydantoin and a catalyst liquid consisting of 20 parts by weight of azobisisobutyronitrile and 200 parts by weight of methyl ethyl ketone are added dropwise at 80 ° C. over 10 hours, whereby the general formula (1-2) Thus, an organic solvent solution of vinyl resin (II) having a hydantoin structure in which R 1 and R 2 are hydrogen atoms was obtained.
  • vinyl resin (II) having a hydantoin structure in which R 1 and R 2 are hydrogen atoms was obtained.
  • a pigment dispersion (II-2) having a pigment concentration of 14.5% by mass was obtained in the same manner as in Example 1 except that the vinyl resin (II) was used instead of the polyurethane (I). It was.
  • An ink for inkjet printing was prepared in the same manner as in Example 1 except that the pigment dispersion (II-2) was used instead of the pigment dispersion (I-2).
  • Example 3 515 parts by mass of polyoxypropylene glycol (number average molecular weight 2000), 120 parts by mass of 2,2-dimethylolpropionic acid and isophorone diisocyanate 305 in a nitrogen-substituted container equipped with a thermometer, a nitrogen gas introduction tube and a stirrer The reaction is carried out at 80 ° C. for 10 hours in the presence of 300 parts by weight of methyl ethyl ketone, which is an organic solvent, and then 50 parts by weight of 1,3-bis (hydrazinocarbonoethyl) -5-isopropylhydantoin) is supplied and reacted. Then, 10 parts by mass of butanol was reacted to obtain an organic solvent solution of polyurethane (III) having a hydantoin structure represented by the general formula (1).
  • polyurethane (III) having a hydantoin structure represented by the general formula (1).
  • a pigment dispersion (III-2) having a pigment concentration of 14.5% by mass was obtained in the same manner as in Example 1, except that the polyurethane (III) was used instead of the polyurethane (I). . Further, an ink for inkjet printing was prepared in the same manner as in Example 1 except that the pigment dispersion (III-2) was used instead of the pigment dispersion (I-2).
  • Example 4 In a nitrogen-substituted container equipped with a thermometer, a nitrogen gas inlet tube, and a stirrer, 267 parts by mass of polyoxypropylene glycol (number average molecular weight 2000), 1,3-bis (2-hydroxyethyl) -5,5 327 parts by mass of a polyester polyol (number average molecular weight 2000) consisting of dimethylimidazolidine-2,4-dione and adipic acid, 120 parts by mass of 2,2-dimethylolpropionic acid and 277 parts by mass of isophorone diisocyanate are methyl ethyl ketone as an organic solvent. In the presence of 300 parts by mass, the reaction is carried out at 80 ° C.
  • a pigment dispersion (IV-2) having a pigment concentration of 14.5% by mass was obtained in the same manner as in Example 1, except that the polyurethane (IV) was used instead of the polyurethane (I). . Further, an ink for inkjet printing was prepared in the same manner as in Example 1 except that the pigment dispersion (IV-2) was used instead of the pigment dispersion (I-2).
  • Example 5 In a nitrogen-substituted container equipped with a thermometer, a nitrogen gas introduction tube, and a stirrer, 310 parts by mass of polyoxypropylene glycol (number average molecular weight 2000), 120 parts by mass of 2,2-dimethylolpropionic acid and isophorone diisocyanate 394 Part by mass is reacted for 10 hours at 80 ° C. in the presence of 300 parts by mass of methyl ethyl ketone, which is an organic solvent, and then 1,3-bis (2-hydroxyethyl) -5,5 dimethylimidazolidine-2,4-dione is added.
  • polyoxypropylene glycol number average molecular weight 2000
  • 2,2-dimethylolpropionic acid and isophorone diisocyanate 394 Part by mass is reacted for 10 hours at 80 ° C. in the presence of 300 parts by mass of methyl ethyl ketone, which is an organic solvent, and then 1,3-bis (2-hydroxy
  • R 1 and R 2 in the general formula (1-1) are methyl groups, and R 3 and R 4 are ethylene groups.
  • An organic solvent solution of polyurethane (V) having a hydantoin structure was obtained.
  • a pigment dispersion (V-2) having a pigment concentration of 14.5% by mass was obtained in the same manner as in Example 1, except that the polyurethane (V) was used instead of the polyurethane (I). . Further, an ink for inkjet printing was prepared in the same manner as in Example 1 except that the pigment dispersion (V-2) was used instead of the pigment dispersion (I-2).
  • Example 6 In a nitrogen-substituted container equipped with a thermometer, a nitrogen gas introduction tube, and a stirrer, 540 parts by mass of polyoxypropylene glycol (number average molecular weight 2000), 120 parts by mass of 2,2-dimethylolpropionic acid and isophorone diisocyanate 301 Part by mass is reacted for 10 hours at 80 ° C. in the presence of 300 parts by mass of methyl ethyl ketone, which is an organic solvent, and then 1,3-bis (2-hydroxyethyl) -5,5 dimethylimidazolidine-2,4-dione is added.
  • polyoxypropylene glycol number average molecular weight 2000
  • 2,2-dimethylolpropionic acid and isophorone diisocyanate 301 Part by mass is reacted for 10 hours at 80 ° C. in the presence of 300 parts by mass of methyl ethyl ketone, which is an organic solvent, and then 1,3-bis (2-hydroxy
  • R 1 and R 2 in the general formula (1-1) are methyl groups, and R 3 and R 4 are ethylene groups.
  • An organic solvent solution of polyurethane (VI) having a certain hydantoin structure was obtained.
  • a pigment dispersion (VI-2) having a pigment concentration of 14.5% by mass was obtained in the same manner as in Example 1, except that the polyurethane (VI) was used instead of the polyurethane (I). . Further, an ink for inkjet printing was prepared in the same manner as in Example 1 except that the pigment dispersion (VI-2) was used instead of the pigment dispersion (I-2).
  • Example 7 In a nitrogen-substituted container equipped with a thermometer, a nitrogen gas inlet tube, and a stirrer, 558 parts by mass of polyoxypropylene glycol (number average molecular weight 2000), 120 parts by mass of 2,2-dimethylolpropionic acid and isophorone diisocyanate 293 Part by mass is reacted for 10 hours at 80 ° C. in the presence of 300 parts by mass of methyl ethyl ketone, which is an organic solvent, and then 1,3-bis (2-hydroxyethyl) -5,5 dimethylimidazolidine-2,4-dione is added.
  • polyoxypropylene glycol number average molecular weight 2000
  • 2,2-dimethylolpropionic acid and isophorone diisocyanate 293 Part by mass is reacted for 10 hours at 80 ° C. in the presence of 300 parts by mass of methyl ethyl ketone, which is an organic solvent, and then 1,3-bis (2-
  • R 1 and R 2 in the general formula (1-1) are methyl groups, and R 3 and R 4 are ethylene groups.
  • An organic solvent solution of polyurethane (VII) having a certain hydantoin structure was obtained.
  • a pigment dispersion (VII-2) having a pigment concentration of 14.5% by mass was obtained in the same manner as in Example 1 except that the polyurethane (VII) was used instead of the polyurethane (I). . Further, an ink for inkjet printing was prepared in the same manner as in Example 1 except that the pigment dispersion (VII-2) was used instead of the pigment dispersion (I-2).
  • Example 8 In a nitrogen-substituted container equipped with a thermometer, a nitrogen gas inlet tube, and a stirrer, 412 parts by mass of polyoxypropylene glycol (number average molecular weight 2000), 120 parts by mass of 2,2-dimethylolpropionic acid and isophorone diisocyanate 357 Part by mass is reacted for 10 hours at 80 ° C. in the presence of 300 parts by mass of methyl ethyl ketone, which is an organic solvent, and then 1,3-bis (2-hydroxyethyl) -5,5 dimethylimidazolidine-2,4-dione is added.
  • polyoxypropylene glycol number average molecular weight 2000
  • 2,2-dimethylolpropionic acid and isophorone diisocyanate 357 Part by mass is reacted for 10 hours at 80 ° C. in the presence of 300 parts by mass of methyl ethyl ketone, which is an organic solvent, and then 1,3-bis (2-
  • Hydantoin in which R 1 and R 2 in the general formula (1-1) are methyl groups and R 3 and R 4 are ethylene groups by supplying and reacting 100 parts by mass and then reacting 11 parts by mass of butanol An organic solvent solution of polyurethane (VIII) having a structure was obtained.
  • a powdery vinyl polymer having a weight average molecular weight of 11000 and an acid value of 156 obtained by polymerizing a vinyl monomer mixture containing 77 parts by mass of styrene, 10 parts by mass of acrylic acid and 13 parts by mass of methacrylic acid.
  • the ion-exchanged water heated to 60 ° C. in a total amount of 1200 parts by mass for 2 hours was added to the kneaded product to obtain a colored resin composition having a nonvolatile content of 34% by mass and a pigment concentration of 21.7% by mass.
  • the precursor of the pigment dispersion was passed through a continuous centrifuge (Kokusan Co., Ltd., Sakai H-600S, 2 L capacity) and centrifuged at a centrifugal force of 18900 G and a residence time of 10 minutes.
  • a pigment dispersion (VIII-2) was obtained by filtration through a 5 ⁇ m filter.
  • the pigment concentration of this pigment dispersion (VIII-2) was 14.2% by mass.
  • Pigment dispersion (VIII-2) pigment concentration 14.2% by mass
  • 28.5 g ⁇ 2-Pyrrolidinone pigment concentration 14.2% by mass
  • 8g ⁇ Triethylene glycol monobutyl ether 8g ⁇ Glycerin
  • 3g ⁇ Surfactant Surfinol 440, manufactured by Air Products
  • 0.5 g ⁇ Ion exchange water 52.0 g
  • Example 9 482 parts by mass of polyoxypropylene glycol (number average molecular weight 2000), 120 parts by mass of 2,2-dimethylolpropionic acid, and tolylene diisocyanate in a nitrogen-substituted container equipped with a thermometer, a nitrogen gas introduction tube, and a stirrer 287 parts by mass are reacted at 80 ° C. for 10 hours in the presence of 300 parts by mass of methyl ethyl ketone as an organic solvent, and then 1,3-bis (2-hydroxyethyl) -5,5 dimethylimidazolidine-2,4-dione
  • R 1 and R 2 are methyl groups
  • R 3 and R 4 are ethylene groups.
  • a polyurethane (IX) organic solvent solution having a hydantoin structure was obtained.
  • Ink for inkjet printing was prepared in the same manner as in Example 1 except that the pigment dispersion (IX-2) was used instead of the pigment dispersion (I-2).
  • Example 10 In a nitrogen-substituted container equipped with a thermometer, a nitrogen gas inlet tube, and a stirrer, 412 parts by mass of polyoxypropylene glycol (number average molecular weight 2000), 1,3-bis (2-hydroxyethyl) -5,5 Reaction of 100 parts by mass of dimethylimidazolidine-2,4-dione, 120 parts by mass of 2,2-dimethylolpropionic acid and 357 parts by mass of isophorone diisocyanate at 80 ° C. for 20 hours in the presence of 300 parts by mass of methyl ethyl ketone as an organic solvent.
  • polyoxypropylene glycol number average molecular weight 2000
  • a pigment dispersion (X-2) having a pigment concentration of 14.5% by mass was obtained in the same manner as in Example 1 except that the polyurethane (X) was used instead of the polyurethane (I). . Further, an ink for inkjet printing was prepared in the same manner as in Example 1 except that the pigment dispersion (X-2) was used instead of the pigment dispersion (I-2).
  • a pigment dispersion (I′-2) having a pigment concentration of 14.5% by mass was prepared in the same manner as in Example 1 except that the polyurethane (I ′) was used instead of the polyurethane (I). Obtained. Further, an ink for inkjet printing was prepared in the same manner as in Example 1 except that the pigment dispersion (I′-2) was used instead of the pigment dispersion (I-2).
  • the precursor of the pigment dispersion was passed through a continuous centrifuge (Kokusan Co., Ltd., Sakai H-600S, 2 L capacity) and centrifuged at a centrifugal force of 18900 G and a residence time of 10 minutes.
  • a pigment dispersion (II′-2) was obtained by filtration through a 5 ⁇ m filter.
  • the pigment concentration of this pigment dispersion (II′-2) was 14.2% by mass.
  • Pigment dispersion (II′-2) (pigment concentration: 14.2% by mass); 28.5 g ⁇ 2-Pyrrolidinone; 8g ⁇ Triethylene glycol monobutyl ether; 8g ⁇ Glycerin; 3g ⁇ Surfactant (Surfinol 440, manufactured by Air Products); 0.5 g ⁇ Ion exchange water; 52.0 g
  • the weight average molecular weight of the compound (A) such as polyurethane was measured by gel permeation chromatograph (GPC method). Specifically, polyurethane was coated on a glass plate with a 3 mil applicator and dried at room temperature for 1 hour to prepare a semi-dry coating film. The obtained coating film was peeled off from the glass plate, and 0.4 g was dissolved in 100 g of tetrahydrofuran to obtain a measurement sample.
  • Tetrahydrofuran was used as the eluent and sample solution, and the weight average molecular weight was measured using an RI detector with a flow rate of 1 mL / min, a sample injection amount of 500 ⁇ L, and a sample concentration of 0.4 mass%.
  • Measuring device High-speed GPC device (“HLC-8220GPC” manufactured by Tosoh Corporation) Column: The following columns manufactured by Tosoh Corporation were connected in series.
  • TKgel G5000 (7.8 mm ID x 30 cm) x 1 "TSKgel G4000” (7.8 mm ID x 30 cm) x 1 "TSKgel G3000” (7.8 mm ID x 30 cm) x 1 “TSKgel G2000” (7.8 mm ID ⁇ 30 cm) ⁇ 1 detector: RI (differential refractometer) Column temperature: 40 ° C Standard sample: A calibration curve was prepared using the following standard polystyrene.
  • the viscosity of the ink and the particle diameter of the dispersed particles in the ink are as follows: It measured by the method similar to the above.
  • Viscosity change rate is less than 2% ⁇ : Viscosity change rate is 2% or more and less than 5% ⁇ : Viscosity change rate is 5% or more
  • Print density The test print obtained above was allowed to stand at room temperature for 24 hours, and then the print density of the solid print image was measured using “SpectroScan Transmission” (manufactured by X-Rite).

Abstract

La présente invention concerne : une dispersion de pigment qui est caractérisée en ce qu'elle contient un pigment et un composé (A) ayant une structure hydantoïne ; un procédé de fabrication de cette dispersion de pigment ; une encre qui contient cette dispersion de pigment ; et une encre pour impression par jet d'encre, qui contient cette dispersion de pigment. Cette dispersion de pigment permet la fabrication d'une encre, notamment d'une encre pour impression par jet d'encre, qui est apte à former une image d'impression nette, tout en ayant une excellente stabilité de dispersion de pigment. L'invention concerne une encre pour impression par jet d'encre, qui est obtenue à l'aide de cette dispersion de pigment, est apte à maintenir une excellente stabilité d'éjection à partir d'une buse d'éjection d'encre pendant une longue période de temps.
PCT/JP2013/074715 2012-09-26 2013-09-12 Dispersion de pigment, encre, encre pour impression par jet d'encre, et procédé de fabrication de dispersion de pigment WO2014050594A1 (fr)

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Cited By (2)

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JP2015174876A (ja) * 2014-03-13 2015-10-05 Dic株式会社 水性顔料分散体、捺染方法及びインクジェット捺染方法
WO2019026805A1 (fr) * 2017-08-02 2019-02-07 花王株式会社 Émulsion polymère

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