WO2015072333A1 - Dispersant de pigment et composition dispersée de pigment contenant ce dernier - Google Patents

Dispersant de pigment et composition dispersée de pigment contenant ce dernier Download PDF

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Publication number
WO2015072333A1
WO2015072333A1 PCT/JP2014/078862 JP2014078862W WO2015072333A1 WO 2015072333 A1 WO2015072333 A1 WO 2015072333A1 JP 2014078862 W JP2014078862 W JP 2014078862W WO 2015072333 A1 WO2015072333 A1 WO 2015072333A1
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Prior art keywords
pigment
block
pigment dispersant
mass
structural unit
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PCT/JP2014/078862
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English (en)
Japanese (ja)
Inventor
光 梅本
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大塚化学株式会社
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Priority to CN201480061892.4A priority Critical patent/CN105722922B/zh
Priority to KR1020167012071A priority patent/KR101917483B1/ko
Publication of WO2015072333A1 publication Critical patent/WO2015072333A1/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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
    • C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
    • B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
    • B41J2/01—Ink jet
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
    • 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
    • C09D17/00—Pigment pastes, e.g. for mixing in paints

Definitions

  • the present invention relates to a pigment dispersant and a pigment dispersion composition containing the same.
  • Ink for printers and the like includes a dye ink in which a dye is dissolved in an aqueous medium as a colorant, and a pigment ink in which a pigment is finely dispersed in an aqueous medium as a colorant. Since dye ink has problems of light resistance and water resistance, it is advantageous to use a pigment ink for applications requiring light resistance and water resistance.
  • pigment dispersion stability is required.
  • an ink jet printer is a printing method in which ink droplets are ejected from fine nozzles to record an image
  • the ink used in this application is required to have high pigment dispersion stability in order not to clog the nozzles. Furthermore, even when nozzle clogging occurs during a long period of rest, it is also required that the causative substance be redissolved by a simple cleaning operation and recovered immediately.
  • Patent Document 1 proposes the use of a polymer compound dispersant obtained by copolymerizing an N-vinylpyrrolidone derivative and an acrylic acid derivative.
  • Patent Document 2 proposes the use of a polymer dispersant comprising a hydrophilic block and a hydrophobic block containing benzyl methacrylate or cyclohexyl methacrylate.
  • the dispersant disclosed in Patent Document 1 is obtained by copolymerizing a hydrophilic monomer with the hydrophilic monomer N-vinylpyrrolidone, it has high solubility in an aqueous medium and has sufficient dispersibility of the pigment. is not.
  • the dispersant disclosed in Patent Document 2 has a pigment derivative as an essential component, and the use of the pigment derivative may cause problems such as poor properties as a pigment and bleeding during printing. is there.
  • An object of the present invention is to provide a pigment dispersant that can be a pigment dispersion composition excellent in dispersion stability, storage stability, and re-dissolution property, and a pigment dispersion composition containing the same.
  • the present invention provides the following pigment dispersant and pigment dispersion composition.
  • Item 1 A block containing a structural unit derived from an N-vinyl lactam monomer, and a B block containing a structural unit derived from a (meth) acrylic acid alkyl ester and a structural unit derived from an acid group-containing vinyl monomer
  • a pigment dispersant which is a block polymer having an acid value of 20 to 140 mgKOH / g.
  • Item 2 The pigment dispersant according to Item 1, wherein the A block contains 80% by mass to 100% by mass of a structural unit derived from an N-vinyl lactam monomer.
  • Item 3 The pigment dispersant according to Item 1 or Item 2, wherein the B block contains 50 mass% to 90 mass% of a structural unit derived from a (meth) acrylic acid alkyl ester.
  • Item 4 The pigment according to any one of Items 1 to 3, wherein a mass ratio of the A block to the B block (A block mass: B block mass) is 10:90 to 70:30. Dispersant.
  • Item 5 The pigment dispersant according to any one of Items 1 to 4, wherein the molecular weight distribution of the block polymer is less than 2.
  • Item 6 The pigment dispersant according to any one of Items 1 to 5, which is a diblock polymer composed of the A block and the block B.
  • Item 7 A pigment dispersion composition comprising the pigment dispersant according to Item 6, a pigment, and an aqueous solvent.
  • Item 8 The pigment dispersion composition according to Item 7, which is for inkjet.
  • a pigment dispersion composition having excellent dispersion stability, storage stability, and re-dissolvability can be obtained.
  • the pigment dispersant of the present invention includes an A block containing a structural unit derived from an N-vinyl lactam monomer, a structural unit derived from a (meth) acrylic acid alkyl ester, and a structural unit derived from an acid group-containing vinyl monomer.
  • “(meth) acryl” means “at least one of acryl and methacryl”.
  • (meth) acrylic acid” means “at least one of acrylic acid and methacrylic acid”.
  • the vinyl monomer means a monomer having a carbon-carbon double bond capable of radical polymerization in the molecule.
  • the A block is a polymer block containing a structural unit derived from an N-vinyl lactam monomer.
  • the structural unit derived from the N-vinyl lactam monomer means a structural unit formed by radical polymerization of the N-vinyl lactam monomer.
  • the carbon can be radically polymerized from the N-vinyl lactam monomer.
  • a structural unit in which a carbon double bond is a carbon-carbon single bond.
  • any vinyl monomer having a lactam ring skeleton can be used without particular limitation, and examples thereof include compounds represented by the following general formula (1).
  • n is an integer from 2 to 12.
  • n is preferably 2 to 8, and more preferably 3 to 4.
  • the group represented by — (CH 2 ) n— constituting the ring may have a substituent, and the substituent is an alkyl group having 1 to 6 carbon atoms, preferably 1 to 2 carbon atoms. An alkyl group is mentioned.
  • N-vinyllactam monomers include N-vinyl-2-pyrrolidone, N-vinylcaprolactam, N-vinyl-4-butylpyrrolidone, N-vinyl-4-propylpyrrolidone, N-vinyl-4-ethyl Pyrrolidone, N-vinyl-4-methyl-5-ethylpyrrolidone, N-vinyl-4-methyl-5-propylpyrrolidone, N-vinyl-5-methyl-5-ethylpyrrolidone, N-vinyl-5-propylpyrrolidone, Examples thereof include N-vinyl-5-butylpyrrolidone, N-vinyl-4-methylcaprolactam, N-vinyl-6-methylcaprolactam, N-vinyl-6-propylcaprolactam, N-vinyl-7-butylcaprolactam and the like. Among these, N-vinyl-2-pyrrolidone
  • N-vinyl lactam monomers can be used alone or in combination of two or more.
  • the A block may be only a structural unit derived from an N-vinyl lactam monomer, or may contain other structural units.
  • the other structural unit may be contained in any form such as random copolymerization or block copolymerization.
  • the A block preferably contains 80% by mass to 100% by mass of structural units derived from N-vinyl lactam monomers, more preferably 90% by mass to 100% by mass, and 95% by mass to 100% by mass. Is more preferable.
  • the A block does not have a structural unit derived from a hydrophobic monomer.
  • the hydrophobic monomer include aromatic group-containing vinyl monomers such as styrene, ⁇ -methylstyrene, benzyl (meth) acrylate, and vinylnaphthalene.
  • the content in the A block is preferably 1% by mass or less.
  • the B block is a polymer block including a structural unit derived from an alkyl (meth) acrylate and a structural unit derived from an acid group-containing vinyl monomer.
  • the structural unit derived from (meth) acrylic acid alkyl ester is a structural unit formed by radical polymerization of (meth) acrylic acid alkyl ester. Specifically, radical polymerization of (meth) acrylic acid alkyl ester is possible.
  • the structural unit derived from an acid group-containing vinyl monomer refers to a structural unit formed by radical polymerization of an acid group-containing vinyl monomer. Specifically, a carbon-carbon duplex capable of radical polymerization of an acid group-containing vinyl monomer.
  • a structural unit in which the bond is a carbon-carbon single bond.
  • the (meth) acrylic acid alkyl ester can be used without particular limitation as long as it is a hydrophobic monomer, and examples thereof include compounds represented by the following general formula (2).
  • R 1 represents a hydrogen atom or a methyl group.
  • R 2 is an alkyl group having 1 to 10 carbon atoms.
  • alkyl group having 1 to 10 carbon atoms in R 2 of the general formula (2) include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group.
  • R 2 is preferably an alkyl group having 1 to 5 carbon atoms.
  • (meth) acrylic acid alkyl esters include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, n-butyl (meth) acrylate, and (meth) acrylic acid.
  • examples include isobutyl, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate.
  • methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, and n-butyl (meth) acrylate are preferable.
  • (Meth) acrylic acid alkyl ester can be used alone or in combination of two or more.
  • the B block preferably contains 50 mass% to 90 mass%, more preferably 60 mass% to 90 mass%, and more preferably 65 mass% to 90 mass% of a structural unit derived from an alkyl (meth) acrylate. It is further preferable to include it.
  • the acid group-containing vinyl monomer can be used without particular limitation as long as it is hydrophilic.
  • the acid group include a carboxyl group, a sulfonic acid group, and a phosphoric acid group, and a carboxyl group is preferable.
  • Examples of the acid group-containing vinyl monomer include conventionally known ones.
  • Specific examples of the carboxyl group-containing vinyl monomer include (meth) acrylic acid, itaconic acid, crotonic acid, maleic acid, fumaric acid, vinyl benzoic acid, (meth) acrylic acid 2-hydroxyethyl and (meth) acrylic acid 4-
  • Examples include monomers obtained by reacting hydroxyalkyl (meth) acrylate such as hydroxybutyl with maleic anhydride, succinic anhydride, and phthalic anhydride.
  • Examples of the monomer having a sulfonic acid group include styrene sulfonic acid, dimethylpropyl sulfonic acid (meth) acrylamide, ethyl sulfonate (meth) acrylate, ethyl sulfonate (meth) acrylamide, and vinyl sulfonic acid.
  • Examples of the monomer having a phosphoric acid group include methacryloyloxyethyl phosphate ester. Among these, (meth) acrylic acid is preferable.
  • One or more acid group-containing vinyl monomers can be used.
  • the B block preferably contains 10 mass% to 50 mass% of structural units derived from the acid group-containing vinyl monomer, more preferably 10 mass% to 40 mass%, and more preferably 10 mass% to 35 mass%. Further preferred.
  • the B block may be a structural unit derived from a (meth) acrylic acid alkyl ester and a structural unit derived from an acid group-containing vinyl monomer, or may contain other structural units.
  • Each structural unit of the B block may be contained in any form such as random copolymerization or block copolymerization.
  • the mass ratio of the A block to the B block is preferably 10:90 to 70:30, and more preferably 30:70 to 50:50.
  • the acid value of the block polymer is 20 to 140 mgKOH / g. It is preferable that the B block contains a structural unit derived from an acid group-containing vinyl monomer so that the acid value of the block polymer falls within this range.
  • the lower limit of the acid value of the block polymer is preferably 40 mgKOH / g, and the upper limit is preferably 130 mgKOH / g.
  • the acid value is less than 20 mgKOH / g, the solubility in an aqueous solvent is poor, and when the acid value is more than 140 mgKOH / g, the solubility in an aqueous solvent is too high, and the dispersibility of the pigment is deteriorated.
  • the lower limit of the weight average molecular weight (Mw) of the block polymer is preferably 6000, and more preferably 10,000.
  • the upper limit of the weight average molecular weight (Mw) of the block polymer is preferably 50000, and more preferably 30000.
  • the molecular weight distribution (PDI) of the block polymer is preferably less than 2, more preferably less than 1.5, and even more preferably less than 1.3.
  • the molecular weight distribution (PDI) is determined by (weight average molecular weight (Mw) of block polymer) / (number average molecular weight (Mn) of block polymer).
  • Mw weight average molecular weight
  • Mn number average molecular weight
  • the smaller the PDI the molecular weight distribution.
  • the polymer has a narrow molecular weight and a uniform molecular weight. When the value is 1.0, the molecular weight distribution has the narrowest width.
  • the larger the PDI the smaller the molecular weight and the larger the molecular weight of the designed polymer, and the worse the dispersibility of the pigment. If the molecular weight is too small, the solubility in an aqueous solvent is too high, and if the molecular weight is too large, the solubility in an aqueous solvent becomes poor
  • the conventional block polymer type dispersant using a block having a hydrophobic substituent as a pigment adsorbing group has insufficient wettability to the pigment due to the formation of micelles having the pigment adsorbing group as a core in an aqueous solution.
  • the block having an N-vinyl lactam group having excellent hydrophilicity acts as a pigment adsorbing group, and the wetting to the pigment proceeds rapidly in an aqueous solution to promote the dispersion of the pigment. I guess that.
  • the dispersion can be stabilized by electrostatic repulsion and steric repulsion by the other block having an acid group.
  • the excellent resolubility is expressed by the highly hydrophilic whole structure.
  • the block polymer having an N-vinyl lactam group can be suitably used as a pigment dispersant in an aqueous medium.
  • the block polymer as a pigment dispersant, the dried precipitate formed from the pigment dispersion composition can be easily redissolved.
  • the method for producing the block polymer is not particularly limited.
  • the block polymer can be obtained by, for example, sequentially polymerizing monomers by block polymerization using a living radical polymerization method or the like. According to the polymerization reaction of the monomer, the A block may be produced first, the B block monomer may be polymerized into the A block, or the B block may be produced first, and the A block monomer may be polymerized into the B block. . In the production of the block polymer, the A block and the B block may be separately produced by the polymerization reaction of the monomers, and then the A block and the B block may be coupled.
  • the block polymer is preferably a diblock polymer composed of an A block and a B block, and usually comprises a bond such as an A block-B block or a B block-A block.
  • the living radical polymerization method is a polymerization method that enables precise control of the molecular structure while maintaining the simplicity and versatility of radical polymerization.
  • the living radical polymerization method includes a method using a transition metal catalyst (ATRP), a method using a sulfur-based reversible chain transfer agent (RAFT), and a method using an organic tellurium compound depending on the method for stabilizing the polymerization growth terminal.
  • ATRP transition metal catalyst
  • RAFT sulfur-based reversible chain transfer agent
  • TERP organic tellurium compound
  • the TERP method is a method of polymerizing a radical polymerizable compound using an organic tellurium compound as a polymerization initiator, and is, for example, a method described in International Publication Nos. 2004/14848 and 2004/14962.
  • R 3 represents an alkyl group having 1 to 8 carbon atoms, an aryl group, or an aromatic heterocyclic group.
  • R 4 and R 5 represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • R 6 represents an alkyl group having 1 to 8 carbon atoms, an aryl group, an aromatic heterocyclic group, an acyl group, an amide group, an oxycarbonyl group or a cyano group.
  • R 3 Te (R 3 Te) 2 (4) (Wherein R 3 represents an alkyl group having 1 to 8 carbon atoms, an aryl group, or an aromatic heterocyclic group.)
  • organic tellurium compound represented by the general formula (3) examples include (methylterranylmethyl) benzene, (methylterranylmethyl) naphthalene, ethyl-2-methyl-2-methylterranyl-propionate, and ethyl-2-methyl.
  • -2-n-butylterranyl-propionate (2-trimethylsiloxyethyl) -2-methyl-2-methylterranyl-propionate
  • (2-hydroxyethyl) -2-methyl-2-methylterranyl-propionate examples include -2-methyl-2-methylterranyl-propinate.
  • Specific examples of the compound represented by the general formula (4) include dimethyl ditelluride, diethyl ditelluride, di-n-propyl ditelluride, diisopropyl ditelluride, dicyclopropyl ditelluride, di-n.
  • the azo polymerization initiator can be used without particular limitation as long as it is an azo polymerization initiator used in normal radical polymerization.
  • 2,2′-azobis isobutyronitrile) (AIBN), 2,2′-azobis (2-methylbutyronitrile) (AMBN), 2,2′-azobis (2,4-dimethylvaleronitrile) (ADVN), 1,1′-azobis (1-cyclohexanecarbonitrile) (ACHN), dimethyl-2,2′-azobisisobutyrate (MAIB), 4,4′-azobis (4-cyanovaleric acid) (ACVA), 1,1′-azobis (1-acetoxy-1-phenylethane), 2,2′-azobis (2-methylbutyramide), 2,2′-azobis (4-methoxy-2,4- Dimethylvaleronitrile) (V-70), 2,2′-azobis (2-methylamidinopropane) dihydrochloride, 2,2′-azobis [2- (2-imida
  • the amount of the compound of the general formula (3) may be appropriately adjusted depending on the physical properties of the target polymer. Usually, the compound of the general formula (3) should be 0.05 to 50 mmol per 1 mol of the monomer. .
  • the compound of the general formula (3) and the azo polymerization initiator are used in combination, it is usually preferable to use 0.01 to 10 mol of the azo polymerization initiator with respect to 1 mol of the compound of the general formula (3).
  • the amount of the compound of the general formula (4) is usually 0.01 to 100 mol with respect to 1 mol of the compound of the general formula (3). Good.
  • the total amount of the compound of the general formula (3) and the compound of the general formula (4) is usually 1 mol.
  • the azo polymerization initiator is preferably 0.01 to 100 mol.
  • the polymerization reaction can be performed without a solvent, but is performed by stirring the above mixture using an organic solvent or an aqueous solvent generally used in radical polymerization.
  • organic solvents that can be used include benzene, toluene, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), acetone, 2-butanone (methyl ethyl ketone), dioxane, hexafluoroisopropaol, chloroform, carbon tetrachloride. , Tetrahydrofuran (THF), ethyl acetate, trifluoromethylbenzene, and the like.
  • aqueous solvent examples include water, methanol, ethanol, isopropanol, n-butanol, ethyl cellosolve, butyl cellosolve, 1-methoxy-2-propanol, diacetone alcohol and the like.
  • the reaction temperature and reaction time may be appropriately adjusted depending on the molecular weight or molecular weight distribution of the polymer to be obtained, but are usually stirred at 0 to 150 ° C. for 1 minute to 100 hours.
  • the TERP method can obtain a high yield and a precise molecular weight distribution even at a low polymerization temperature and a short polymerization time.
  • the target polymer After completion of the polymerization reaction, the target polymer can be separated from the obtained reaction mixture by a usual separation and purification means.
  • the pigment dispersion composition according to this embodiment includes a pigment dispersant composed of the block polymer, a pigment, and an aqueous solvent.
  • the pigment dispersant of the present invention is preferably used after neutralizing acid groups.
  • neutralizing and using the acid group By neutralizing and using the acid group, the dispersion state of the pigment becomes stable, and a pigment dispersion composition having excellent long-term storage stability can be obtained.
  • Neutralization includes, for example, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, organic amines such as ammonia, dimethylamine, diethylamine, triethylamine, monoethanolamine, diethanolamine, triethanolamine, and dimethylethanolamine. Etc. can be used.
  • the ratio of acid groups to be neutralized is preferably 30 to 100%, more preferably 80 to 100%.
  • the blending amount of the pigment dispersant in the pigment dispersion composition of the present invention is preferably 5 parts by mass to 100 parts by mass with respect to 100 parts by mass of the pigment, and preferably 10 parts by mass to 70 parts by mass. More preferably, it is 50 parts by mass. If the blending amount of the pigment dispersant is too small, the pigment cannot be sufficiently dispersed, and if the blending amount of the pigment dispersant is too large, a pigment dispersant not adsorbed on the pigment is present in the liquid. Absent.
  • any of organic pigments and inorganic pigments can be used without particular limitation, and examples thereof include red, yellow, orange, blue, green, purple, and black pigments. It is done.
  • Organic pigments include monoazo, diazo, and condensed diazo pigments, diketopyrrolopyrrole, phthalocyanine, isoindolinone, isoindoline, quinacridone, indigo, thioindigo, and quinophthalone. And dioxazine-based, anthraquinone-based, perylene-based and perinone-based polycyclic pigments.
  • examples of inorganic pigments include carbon black pigments such as furnace black, lamp black, acetylene black, and channel black.
  • the pigment contained in the pigment dispersion composition by selecting the pigment type, particle size, and treatment type according to the purpose. Moreover, only one type of pigment may be contained in the pigment dispersion composition, or a plurality of types may be used.
  • pigments include C.I. I. Pigment Red 7, 9, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 122, 123, 146, 149, 168, 177, Red pigments such as 178, 179, 187, 200, 202, 208, 210, 215, 224, 254, 255, 264; I.
  • Orange pigments such as Pigment Orange 36, 38, 43;
  • Blue pigments such as Pigment Blue 15, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60;
  • Green pigments such as Pigment Green 7, 36, 58; I. Purple pigments such as Pigment Violet 19, 23, 32, 50; I.
  • black pigments such as Pigment Black 7.
  • C.I. I. Pigment Red 122, C.I. I. Pigment Yellow 74, 128, 155, C.I. I. Pigment Blue 15: 3, 15: 4, 15: 6, C.I. I. Green 7, 36, C.I. I. Pigment Violet 19, C.I. I. Pigment Black 7 or the like is preferable.
  • the pigment concentration in the pigment dispersion composition of the present invention is not particularly limited as long as it provides a sufficient coloring concentration to the recording material, but is preferably 1% by mass to 30% by mass, and preferably 1% by mass to 20%. More preferably, it is more preferably 1% by mass to 10% by mass. If it exceeds 30% by mass, the density of the pigment in the liquid becomes high, which may cause a problem of aggregation due to hindering free movement of the pigment particles.
  • aqueous solvent used in the present invention water or a water-soluble organic solvent can be used, and these may be used alone or in combination.
  • water it is preferable to use pure water or ion exchange water (deionized water).
  • Water-soluble organic solvents include alcohols such as methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, tert-butyl alcohol; ethylene glycol, propylene glycol, butylene glycol, tri Glycols such as ethylene glycol, 1,2,6-hexanetriol, thiodiglycol, hexylene glycol, diethylene glycol; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, triethylene glycol monomethyl ether , Triethylene glycol monoethyl ether, triethylene glycol monobutyl ether G
  • a conventionally known method can be applied and is not particularly limited. For example, it is obtained by mixing the pigment dispersant of the present invention neutralized with an alkali, the pigment, and an aqueous solvent using, for example, a mixing and dispersing machine such as a paint shaker, a bead mill, a ball mill, a dissolver, or a kneader. It is done.
  • a mixing and dispersing machine such as a paint shaker, a bead mill, a ball mill, a dissolver, or a kneader.
  • the pigment dispersion composition of the present invention may contain other additives as necessary.
  • other additives include a viscosity modifier, a surface tension modifier, a penetrating agent, a pigment derivative, an antioxidant, an ultraviolet absorber, an antiseptic, and an antifungal agent.
  • the pigment dispersant of the present invention can give excellent dispersion stability and storage stability to a pigment in an aqueous medium, and is excellent in re-solubility.
  • the re-solubility means the ease of dissolution when the solvent in the pigment dispersion composition is volatilized and the dried dried precipitate is dissolved again in the solvent. Therefore, the pigment dispersion composition containing the pigment dispersant of the present invention can be suitably used as an inkjet ink.
  • the weight ratio, weight average molecular weight (Mw), molecular weight distribution (PDI) and acid value of the pigment dispersant and pigment dispersion composition, and the viscosity, storage stability and resolubility of the pigment dispersion composition are as follows. Measured or evaluated according to
  • Polymerization rate 1 H-NMR was measured using NMR (trade name: AVANCE500, manufactured by Bruker BioSpin Corporation), and the polymerization rate was calculated from the area ratio between the vinyl group of the monomer and the polymer peak.
  • a sample dissolved in tetrahydrofuran (hereinafter referred to as “THF”) was titrated with a 0.1 M potassium hydroxide / 2-propanol solution using a potentiometric titrator (trade name: GT-200, manufactured by Mitsubishi Chemical Corporation).
  • the acid value was calculated by the following formula using the inflection point of the titration pH curve as the titration end point.
  • A 56.11 ⁇ Vs ⁇ 0.1 ⁇ f / w
  • w Weight of sample to be measured (g) (solid content conversion)
  • Viscosity change rate (%) ⁇ (viscosity after storage) / (viscosity before storage) ⁇ ⁇ 100
  • Example 1 Pigment dispersant A
  • N-vinylpyrrolidone manufactured by Nippon Shokubai Co., Ltd., hereinafter referred to as “VP”
  • VP N-vinylpyrrolidone
  • deionized water 1.94 g
  • 2,2′-azobis 0.0259 g of (4-methoxy-2,4-dimethylvaleronitrile) manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “V-70”
  • V-70 4-methoxy-2,4-dimethylvaleronitrile
  • N-butyl acrylate Nahon Shokubai Co., Ltd., hereinafter referred to as “BA”) 6.86 g, acrylic acid (Sigma Aldrich Japan Co., Ltd., hereinafter referred to as “AA”) 1.54 g, 2. 2'-azobis (2,4-dimethylvaleronitrile) (manufactured by Otsuka Chemical Co., Ltd., hereinafter referred to as “ADVN”) 0.0596 g, THF 8.00 g, methanol 3.59 g mixed solution was added and reacted at 45 ° C. for 39 hours. I let you. The polymerization rate was 98% for both BA and AA.
  • Example 2 Pigment dispersant B A flask equipped with an argon gas introduction tube and a stirring bar was charged with 6.00 g of VP, 3.23 g of deionized water, 0.360 g of BTEE, and 0.0259 g of V-70, and reacted at 30 ° C. for 8 hours. The polymerization rate was 98%, Mw was 6,100, and PDI was 1.17.
  • a mixed solution of 4.46 g of BA, 1.54 g of AA, 0.0596 g of ADVN, 7.11 g of THF and 4.03 g of methanol was added to the reaction solution in advance, and the mixture was reacted at 45 ° C. for 38 hours.
  • the polymerization rates were BA 97% and AA 96%, respectively.
  • Example 3 Pigment dispersant C A flask equipped with an argon gas introduction tube and a stirring bar was charged with 6.00 g of VP, 3.23 g of deionized water, 0.360 g of BTEE, and 0.0259 g of V-70, and reacted at 30 ° C. for 8 hours. The polymerization rate was 98%, Mw was 6,100, and PDI was 1.17.
  • a mixed solution of BA 5.34 g, AA 0.660 g, ADVN 0.0596 g, THF 7.10 g, and MeOH 4.94 g previously substituted with argon was added to the above reaction solution, and reacted at 45 ° C. for 38 hours.
  • the polymerization rates were BA 97% and AA 96%, respectively.
  • Example 4 Pigment dispersant D A flask equipped with an argon gas introduction tube and a stirring bar was charged with 6.00 g of VP, 3.23 g of deionized water, 0.360 g of BTEE, and 0.0259 g of V-70, and reacted at 30 ° C. for 8 hours. The polymerization rate was 98%, Mw was 6,100, and PDI was 1.17.
  • a mixed solution of 4.90 g of BA, 1.90 g of AA, 0.0596 g of ADVN, 7.11 g of THF, and 4.03 g of methanol was added to the reaction solution in advance and reacted at 45 ° C. for 38 hours.
  • the polymerization rates were BA 97% and AA 96%, respectively.
  • Example 5 Pigment dispersant E A flask equipped with an argon gas introduction tube and a stirring bar was charged with 6.00 g of VP, 3.23 g of deionized water, 0.360 g of BTEE, and 0.0259 g of V-70, and reacted at 30 ° C. for 12 hours. The polymerization rate was 100%, Mw was 6,100, and PDI was 1.17.
  • the polymerization rates were BA 97% and AA 100%, respectively.
  • Example 6 Pigment dispersant F A flask equipped with an argon gas inlet tube and a stir bar was charged with 3.60 g of VP, 1.94 g of deionized water, 0.360 g of BTEE, and 0.0259 g of V-70, and reacted at 30 ° C. for 24 hours. The polymerization rate was 100%, Mw was 3,450, and PDI was 1.17.
  • Example 7 Pigment dispersant G A flask equipped with an argon gas inlet tube and a stir bar was charged with 3.60 g of VP, 1.94 g of deionized water, 0.360 g of BTEE, and 0.0259 g of V-70, and reacted at 30 ° C. for 24 hours. The polymerization rate was 100%, Mw was 3,450, and PDI was 1.17.
  • CHA cyclohexyl acrylate
  • Example 8 Pigment dispersant H A flask equipped with an argon gas introduction tube and a stirring bar was charged with 6.00 g of VP, 3.23 g of deionized water, 0.180 g of BTEE, and 0.0259 g of V-70, and reacted at 30 ° C. for 15 hours. The polymerization rate was 100%, Mw was 11,400, and PDI was 1.15.
  • a mixed solution of 4.46 g of BA, 1.54 g of AA, 0.0745 g of ADVN, 7.11 g of THF, and 4.03 g of methanol was added to the reaction solution in advance and reacted at 45 ° C. for 46 hours.
  • the polymerization rates were BA 99% and AA 95%, respectively.
  • Pigment dispersant I A flask equipped with an argon gas introduction tube and a stirring bar was charged with 6.00 g of VP, 3.23 g of deionized water, 0.360 g of BTEE, and 0.0259 g of V-70, and reacted at 30 ° C. for 12 hours. The polymerization rate was 100%, Mw was 6,100, and PDI was 1.17.
  • a mixed solution of 3.69 g of BA, 2.31 g of AA, 0.0596 g of ADVN, 7.11 g of THF, and 4.03 g of methanol was added to the reaction solution in advance and reacted at 45 ° C. for 40 hours.
  • the polymerization rates were BA 97% and AA 100%, respectively.
  • Comparative Example 2 Pigment dispersant J A flask equipped with an argon gas introduction tube and a stirring bar was charged with 6.00 g of VP, 3.23 g of deionized water, 0.360 g of BTEE, and 0.0259 g of V-70, and reacted at 30 ° C. for 15 hours. The polymerization rate was 100%, Mw was 5,700, and PDI was 1.13.
  • a mixed solution of BA 6.00 g, ADVN 0.0894 g, THF 7.11 g, and methanol 4.03 g previously substituted with argon was added to the above reaction solution, and reacted at 45 ° C. for 40 hours.
  • the polymerization rate was 97%.
  • a mixed solution of AA 1.73 g, ADVN 0.0335 g, THF 6.27 g, and MeOH 3.56 g previously substituted with argon was added to the above reaction solution, and reacted at 45 ° C. for 46 hours. Furthermore, 0.0333 g of AIBN was added and reacted at 60 ° C. for 27 hours. The polymerization rate was 86%.
  • reaction solution was poured into a mixture of 0.7 L of ethyl acetate and 0.7 L of heptane.
  • the pigment dispersant L was obtained by suction-filtering the polymer which precipitated and drying. Mw was 8,730, PDI was 1.61, and the acid value was 108 mgKOH / g.
  • Example 9 An amount of potassium hydroxide that neutralizes 95% of the acid groups of the pigment dispersant was dissolved in water, and then pigment dispersant A was added to prepare a 15% by mass aqueous solution of the pigment dispersant.
  • aqueous pigment dispersant prepared above, 20 parts by mass of pigment (CI Pigment Blue 15: 3, trade name: CHROMOPHTAL BLUE 4GNP, manufactured by Ciba Specialty Chemicals), 27 parts by mass of deionized water
  • the blending composition was adjusted so that 400 parts by weight of 0.3 mm zirconia beads was added, and mixed for 5 hours with a bead mill (trade name: DISPERMAT CA, VMA-GETZMANN GmbH) and sufficiently dispersed. After the dispersion was completed, the beads were filtered to obtain a pigment dispersion (pigment composition).
  • Example 10 The same operation as in Example 9 was performed except that the pigment dispersant was changed to the pigment dispersant B.
  • Example 11 The same operation as in Example 9 was performed except that the pigment dispersant was changed to the pigment dispersant C.
  • Example 12 The same operation as in Example 9 was performed except that the pigment dispersant was changed to the pigment dispersant D.
  • Example 13 The same operation as in Example 9 was performed except that the pigment dispersant was changed to the pigment dispersant E.
  • Example 14 The same operation as in Example 9 was performed except that the pigment dispersant was changed to the pigment dispersant F.
  • Example 15 The same operation as in Example 9 was performed except that the pigment dispersant was changed to the pigment dispersant G.
  • Example 16 The pigment dispersant was changed to pigment dispersant B, and the pigment was changed to C.I. I. It implemented similarly to Example 9 except having changed to Pigment Yellow 74 (brand name: HANSA Yellow 5GX01, product made by Clariant).
  • Example 17 The pigment dispersant was changed to pigment dispersant B, and the pigment was changed to C.I. I.
  • Pigment Black 7 (trade name: Carbon Black MA-100, manufactured by Mitsubishi Chemical Corporation) was used.
  • Example 18 The pigment dispersant was changed to Pigment Dispersant H, and the pigment was changed to C.I. I. Changed to Pigment Red 122 (trade name: Cinquasia Magenta D4550J, manufactured by BASF) The same operation as in Example 9 was performed except that.
  • Example 6 (Comparative Example 6) The same operation as in Example 9 was performed except that the pigment dispersant was changed to the pigment dispersant I.
  • Pigment dispersant J was added to water. However, the pigment dispersant J could not be dissolved in water.
  • Comparative Example 9 The same procedure as in Comparative Example 8 was carried out except that the pigment dispersant was changed to the pigment dispersant L. However, the pigment could not be dispersed.
  • any of the examples it was shown that an ink having low viscosity, high storage stability, and good re-dissolvability can be obtained. From this result, it was confirmed that the pigment dispersant of the present invention is useful for general pigments used in inkjet inks.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Graft Or Block Polymers (AREA)
  • Ink Jet (AREA)

Abstract

L'invention concerne : un dispersant de pigment qui permet d'obtenir une composition dispersée de pigment ayant d'excellentes caractéristiques en termes de stabilité de dispersion, de stabilité au stockage et de resolubilité; une composition dispersée de pigment contenant le dispersant de pigment. Le dispersant de pigment est un polymère à blocs qui comprend un bloc (A) contenant un motif de structure issu d'un monomère de type N-vinyllactame et un bloc (B) contenant un motif de structure issu d'un ester alkylique d'acide (méth)acrylique et un motif de structure issu d'un monomère vinylique contenant un groupe acide, et qui possède un indice d'acide de 20 à 140 mg de KOH/g.
PCT/JP2014/078862 2013-11-12 2014-10-30 Dispersant de pigment et composition dispersée de pigment contenant ce dernier WO2015072333A1 (fr)

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CN110305270A (zh) * 2019-06-13 2019-10-08 清远市简一陶瓷有限公司 一种水溶性ab型嵌段聚合物、其制备方法及应用
JP2020180215A (ja) * 2019-04-25 2020-11-05 大塚化学株式会社 表面改質剤組成物
TWI713710B (zh) * 2016-03-16 2020-12-21 日商Ｄｎｐ精細化工股份有限公司 彩色濾光片用著色樹脂組成物、顏料分散液、彩色濾光片及顯示裝置

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JP7124557B2 (ja) * 2018-08-23 2022-08-24 セイコーエプソン株式会社 インク組成物
JP7329956B2 (ja) * 2019-04-25 2023-08-21 大塚化学株式会社 Ｎ－アルケニルラクタム系ブロック共重合体を含有する重合生成物および重合生成物の製造方法
CN110819162A (zh) * 2019-10-25 2020-02-21 温州大邦笔墨科技有限公司 一种易清洁白板笔墨水及其制备方法

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TWI713710B (zh) * 2016-03-16 2020-12-21 日商Ｄｎｐ精細化工股份有限公司 彩色濾光片用著色樹脂組成物、顏料分散液、彩色濾光片及顯示裝置
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CN110305270A (zh) * 2019-06-13 2019-10-08 清远市简一陶瓷有限公司 一种水溶性ab型嵌段聚合物、其制备方法及应用
CN110305270B (zh) * 2019-06-13 2022-03-08 清远市简一陶瓷有限公司 一种水溶性ab型嵌段聚合物、其制备方法及应用

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