CN112745715A - Oil-based inkjet ink, method for producing oil-based inkjet ink, and method for producing dispersant - Google Patents
Oil-based inkjet ink, method for producing oil-based inkjet ink, and method for producing dispersant Download PDFInfo
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- CN112745715A CN112745715A CN202011081763.5A CN202011081763A CN112745715A CN 112745715 A CN112745715 A CN 112745715A CN 202011081763 A CN202011081763 A CN 202011081763A CN 112745715 A CN112745715 A CN 112745715A
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- water
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D11/36—Inkjet printing inks based on non-aqueous solvents
-
- 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
- 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
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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
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Abstract
The present invention relates to an oil-based ink jet ink, a method for producing an oil-based ink jet ink, and a method for producing a dispersant. [ problem ] to]Providing: an oily ink jet ink which is less likely to cause aggregation. [ solution ]]An oil-based inkjet ink comprising: a pigment; a dispersant comprising an acidic resin, a low-molecular amine compound, and a (methyl) group containing at least 1 group selected from the group consisting of a group represented by the following general formula (1) and a group represented by the following general formula (2)Acrylic resin formation; and a nonaqueous solvent. In the general formula (1), R1And R2Each independently represents a hydrogen atom or a substituent, R1And R2Optionally bonded to each other to form a ring. In the general formula (2), R3Represents a substituent group, R4Represents a hydrogen atom or a substituent, R3And R4Optionally bonded to each other to form a ring.
Description
Technical Field
Embodiments of the present invention relate to an oil-based inkjet ink, a method for producing an oil-based inkjet ink, and a method for producing a dispersant.
Background
The ink jet recording method is as follows: an inkjet ink having high fluidity is ejected as droplets from fine nozzles, and images are recorded on a recording medium provided opposite the nozzles, and high-speed printing can be performed with low noise. As inks used in such an ink jet recording system, there are known: an aqueous ink containing water as a main solvent, an ultraviolet-curable ink (UV ink) containing a polymerizable monomer at a high content as a main component, a hot-melt ink (solid ink) containing a wax at a high content as a main component, and a so-called non-aqueous ink containing a non-aqueous solvent as a main solvent. The non-aqueous ink can be classified into a solvent ink (solvent-based ink) in which a volatile organic solvent is used as a main solvent, and an oil-based ink (oil-based ink) in which an organic solvent having low volatility or non-volatility is used as a main solvent. The solvent ink is mainly dried on the recording medium by evaporation of the organic solvent, and the oil-based ink is mainly dried by permeation of the recording medium.
Patent document 1 discloses a colored resin particle dispersion containing colored resin particles containing a phosphated solid resin and/or a nitrated solid resin, and an inkjet ink containing the same.
Patent document 2 discloses a colored resin particle dispersion containing colored resin particles containing a solid resin and a liquid organic compound having an acidic group, and an inkjet ink containing the same.
Patent document 3 discloses an oil-based inkjet ink containing an encapsulated pigment containing a urethane compound and a non-aqueous solvent, wherein the urethane compound has a urethane skeleton and a side chain containing a carboxyl group or the like, and is a compound insoluble in the non-aqueous solvent.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2015-134850
Patent document 2: japanese patent laid-open publication No. 2015-134852
Patent document 3: japanese laid-open patent publication No. 2018-48293
Disclosure of Invention
Problems to be solved by the invention
When the ink receives a force from the outside, for example, when the liquid sending pump slides the ink in the ink passage, aggregates may be generated. An object of an embodiment of the present invention is to provide: an oily ink jet ink which is less likely to cause aggregation.
Means for solving the problems
One embodiment of the present invention relates to an oil-based inkjet ink including: a pigment; a dispersant formed of an acidic resin, a low-molecular amine compound, and a (meth) acrylic resin containing at least 1 group selected from the group consisting of a group represented by the following general formula (1) and a group represented by the following general formula (2); and a nonaqueous solvent.
In the general formula (1), R1And R2Each independently represents a hydrogen atom or a substituent, R1And R2Optionally bonded to each other to form a ring. In the general formula (2), R3Represents a substituent group, R4Represents a hydrogen atom or a substituent, R3And R4Optionally bonded to each other to form a ring.
Another embodiment of the present invention relates to a method for producing an oil-based inkjet ink, including the steps of: a step of obtaining a water-in-oil emulsion comprising: a continuous phase containing a nonaqueous solvent and a (meth) acrylic resin containing at least 1 group selected from the group consisting of a group represented by the following general formula (1) and a group represented by the following general formula (2), and a dispersed phase containing water, an acidic water-dispersible resin, and a low-molecular amine compound; a step of removing water from the water-in-oil emulsion to obtain a dispersant dispersion; and a step of mixing the dispersant dispersion with a pigment to disperse the pigment.
(in the general formula (1), R1And R2Each independently represents a hydrogen atom or a substituent, R1And R2Optionally bonded to each other to form a ring. In the general formula (2), R3Represents a substituent group, R4Represents a hydrogen atom or a substituent, R3And R4Optionally bonded to each other to form a ring. )
Another embodiment of the present invention relates to a method for producing a dispersant, including the steps of: a step of obtaining a water-in-oil emulsion comprising: a continuous phase containing a nonaqueous solvent and a (meth) acrylic resin containing at least 1 group selected from the group consisting of a group represented by the following general formula (1) and a group represented by the following general formula (2), and a dispersed phase containing water, an acidic water-dispersible resin, and a low-molecular amine compound; and a step of removing water from the water-in-oil emulsion.
In the general formula (1), R1And R2Each independently represents a hydrogen atom or a substituent, R1And R2Optionally bonded to each other to form a ring. In the general formula (2), R3Represents a substituent group, R4Represents a hydrogen atom or a substituent, R3And R4Optionally bonded to each other to form a ring.
ADVANTAGEOUS EFFECTS OF INVENTION
According to an embodiment of the present invention, there may be provided: an oily ink jet ink which is less likely to cause aggregation.
Detailed Description
Hereinafter, embodiments of the present invention will be described, but the following embodiments do not limit the present invention.
Hereinafter, the oil-based ink jet ink is sometimes referred to as "ink" or "oil-based ink".
An oil-based inkjet ink according to an embodiment of the present invention is an oil-based inkjet ink including: a pigment; a dispersant (hereinafter, also simply referred to as "dispersant" in some cases) formed of an acidic resin, a low-molecular amine compound, and a (meth) acrylic resin containing at least 1 group selected from the group consisting of a group represented by the following general formula (1) and a group represented by the following general formula (2); and a nonaqueous solvent.
In the general formula (1), R1And R2Each independently represents a hydrogen atom or a substituent, R1And R2Optionally bonded to each other to form a ring. In the general formula (2), R3Represents a substituent group, R4Represents a hydrogen atom or a substituent, R3And R4Optionally bonded to each other to form a ring.
Hereinafter, a (meth) acrylic resin containing at least 1 group selected from the group consisting of a group represented by the following general formula (1) and a group represented by the following general formula (2) may be referred to as a "(meth) acrylic resin a".
In the ink, if a compound having a free acidic group is present in the periphery of the pigment, the aggregating force of the pigment tends to be increased, and if such an ink is subjected to an external force such as sliding, aggregates tend to be easily generated. The oil-based inkjet ink of the present embodiment uses a dispersant composed of an acidic resin, a low-molecular amine compound, and a (meth) acrylic resin a, and thus can form an ink in which aggregates are not easily generated even when an external force such as sliding is applied. Without being bound by a particular theory, it is presumed that the reason is that in the dispersant, the basic group of the low-molecular amine compound is bonded to the acidic group of the acidic resin, or at least 1 group selected from the group consisting of the group represented by the general formula (1) and the group represented by the general formula (2) is made to have affinity with the acidic group, thereby reducing the amount of free acidic groups and making it difficult to aggregate the pigment.
The method for producing the oil-based ink-jet ink of the present embodiment is not particularly limited, and for example, the ink-jet ink can be produced by a method using a water-in-oil (W/O) emulsion drying method described later.
The oil-based inkjet ink may contain a pigment.
As pigments, it is possible to use: organic pigments such as azo pigments, phthalocyanine pigments, polycyclic pigments, and dye-based lake pigments, and inorganic pigments such as carbon black and metal oxides.
Examples of the azo pigment include soluble azo lake pigments, insoluble azo pigments, and condensed azo pigments. Examples of the phthalocyanine pigment include a metal phthalocyanine pigment and a metal-free phthalocyanine pigment. Examples of the polycyclic pigment include quinacridone pigments, perylene pigments, perinone pigments, isoindoline pigments, isoindolinone pigments, dioxazine pigments, thioindigo pigments, anthraquinone pigments, quinophthalone pigments, metal complex pigments, and Diketopyrrolopyrrole (DPP). Examples of the carbon black include furnace black, lamp black, acetylene black, and channel black. Examples of the metal oxide include titanium oxide and zinc oxide. These pigments may be used alone or in combination of 2 or more.
The cyan ink preferably contains copper phthalocyanine blue from the viewpoint that a printed matter of high chroma can be obtained. The yellow ink preferably contains any of monoazo yellow, disazo yellow, and benzimidazolone yellow, and more preferably contains disazo yellow. The magenta ink preferably contains any of azo lake red, naphthol AS, benzimidazolone red, quinacridone magenta, and more preferably contains azo lake red.
The pigment may be dispersed in a form in which colored resin particles containing a pigment and a dispersant are formed and dispersed. The colored resin particles containing a pigment and a dispersant may be, for example, so-called encapsulated pigments obtained by covering a pigment with a dispersant.
The average particle diameter of the pigment is preferably 300nm or less, more preferably 200nm or less, from the viewpoint of ejection stability and storage stability.
The pigment is usually 0.01 to 20% by mass relative to the total amount of the ink, and preferably 1 to 15% by mass from the viewpoint of image density and ink viscosity.
The oil-based inkjet ink may contain a dispersant formed of an acidic resin, a low-molecular amine compound, and a (meth) acrylic resin a. The dispersant may be formed using at least an acidic resin, a low-molecular amine compound, and a (meth) acrylic resin a, and may be formed using other components in addition to the acidic resin, the low-molecular amine compound, and the (meth) acrylic resin a.
The dispersant is preferably used in the form of resin particles in the production process of the oil-based inkjet ink. For example, when the dispersant is produced by a method of drying in oil using a water-in-oil (W/O) emulsion, the dispersant is preferably produced in the form of resin particles.
In the oil-based inkjet ink, for example, a dispersant and a pigment are preferably contained in the colored resin particles. Examples of such colored resin particles include those in which a dispersant is covered with a pigment.
The acidic resin is not particularly limited, and examples thereof include: acidic polyurethane-based resins, acidic polyester-based resins, acidic (meth) acrylic resins, acidic urethane (meth) acrylic resins, acidic (meth) acrylic silicone-based resins, acidic vinyl chloride-based resins, acidic styrene (meth) acrylic resins, and the like. The acidic resin is preferably an acidic urethane resin or an acidic (meth) acrylic resin, and more preferably an acidic urethane resin, from the viewpoint of improving the abrasion resistance.
The polyurethane resin has a urethane group. The urethane group of the polyurethane resin can be usually obtained by a reaction between a polyol and a polyisocyanate, and in the acidic polyurethane resin, from the viewpoint of storage stability, an aliphatic polyisocyanate is preferably used as the polyisocyanate.
As the acidic polyurethane resin, from the viewpoint of improving the abrasion resistance, an acidic polyurethane urea resin having a urea group in addition to a urethane group is preferable. The polyurethane urea resin can be obtained, for example, as follows: the urethane prepolymer obtained from a material containing a polyol and a polyisocyanate is reacted with water and/or a polyamine compound, and the isocyanate group of the urethane prepolymer is reacted with water and/or a polyamine compound to generate a urea group and to extend the chain.
The acidic urethane resin also includes an acidic urethane (meth) acrylic resin, and the acidic urethane resin is also included in the acidic (meth) acrylic resin.
(meth) acrylic acid means a resin comprising methacrylic acid, acrylic acid, or a combination thereof, and (meth) acrylic resin means a resin comprising methacrylic acid units, a resin comprising acrylic acid units, or a resin comprising both of these units.
The acidic resin may be a resin having an acidic group, and an acidic water-dispersible resin may be used as a raw material in the production of the ink. The acidic resin is preferably a resin having an acidic group, and the acidic group is preferably a carboxyl group, a sulfo group, a phosphoric acid group, or the like.
The acidic resin is preferably a resin which is solid at 23 ℃.
The solubility of the acidic resin in the nonaqueous solvent is preferably 1g or less in terms of the amount of the resin that can be dissolved in 100g of the nonaqueous solvent at 23 ℃. Further, since the acidic resin is not easily soluble in a non-aqueous solvent, it is also advantageous in reducing the viscosity of the ink.
The weight average molecular weight of the acidic resin varies depending on the type of the resin, and is, for example, preferably 5000 to 200000, more preferably 10000 to 150000. For example, the weight average molecular weight of the acidic polyurethane resin is preferably 5000 to 50000, more preferably 10000 to 30000. The weight average molecular weight of the acidic (meth) acrylic resin is preferably 10000 to 200000, more preferably 30000 to 150000.
The weight average molecular weight of the resin was determined by GPC method in terms of standard polystyrene. The same applies to the weight average molecular weight in the resins and the like described below.
For example, when the dispersant is produced by a method of drying in oil using a water-in-oil (W/O) emulsion, an acidic water-dispersible resin is preferably used for forming the acidic resin. In the production of the ink, the acidic water-dispersible resin is desirably added in the form of a dispersion (oil-in-water (O/W) resin emulsion) dispersed in a liquid such as water in advance. In the case of using the aqueous dispersion, water contained in the aqueous dispersion is preferably removed in the ink production process.
The acidic water-dispersible resin may be a resin having acidic groups on the particle surface, such as a self-emulsifying resin, or the resin particle surface may be subjected to surface treatment such as adhesion of an acidic dispersant. The acidic resin may be obtained from any of them. The acidic group is typically a carboxyl group, a sulfo group, a phosphate group, or the like. The acidic dispersant is an anionic surfactant or the like.
The method for synthesizing the acidic polyurethane resin is not particularly limited. The acidic polyurethane resin can be obtained by reacting a polyol with a polyisocyanate, for example.
Examples of the polyhydric alcohol include polytetramethylene glycol, 2-dimethylolbutanoic acid, 1, 4-butanediol, and diethanolamine. As the polyol, for example, a diol obtained by a michael addition reaction of a dialkanolamine such as diethanolamine and a compound having an acryloxy group such as acrylic acid can be used. These polyols may be used alone in 1 kind, or in combination of 2 or more kinds. At least 1 of the polyols used preferably has acidic groups.
As the polyisocyanate, for example, diisocyanate such as hexamethylene diisocyanate can be used. The polyisocyanate may be used alone in 1 kind, or in combination of 2 or more kinds.
The acidic polyurethane urea resin can be obtained, for example, as follows: the urethane prepolymer is obtained by reacting a polyol with a polyisocyanate to obtain a urethane prepolymer, and then reacting the obtained urethane prepolymer with water and/or a polyamine compound. For the polyols and polyisocyanates, the same is as above. As the polyamine compound, for example, hexamethylenediamine or the like can be used.
The method for synthesizing the acidic (meth) acrylic resin is not particularly limited. For example, it can be obtained by polymerizing 1 or 2 or more kinds of monomers selected from (meth) acrylic acid esters such as alkyl (meth) acrylates, and (meth) acrylic acids. At least 1 of the monomers used in the synthesis of the acidic (meth) acrylic resin preferably has an acidic group.
The aqueous dispersion of an acidic water-dispersible resin is obtained by dispersing a resin in water such as ion-exchanged water, and when the aqueous dispersion is produced by dispersing a resin in water, a low-molecular amine compound described later is preferably added. To an aqueous dispersion of a commercially available acidic water-dispersible resin, a low-molecular amine compound may be added.
Examples of commercially available aqueous dispersions of acidic water-dispersible polyurethane resins include: "WS 5984" (trade name), "WS 4022" (trade name), "Superflex 740" (trade name), "Superflex 150H" (trade name), "UCOAT UWS-145" (trade name), Daicel Ornex Co., Ltd, "DAOTAN TW-6493" (trade name), and "DAOTAN TW-6490" (trade name), which are manufactured by Mitsui chemical Co., Ltd.
Examples of commercially available aqueous dispersions of acidic water-dispersible urethane (meth) acrylic resins include: and "DAOTAN VTW-1262" (trade name) manufactured by Daicel Ornex Co., Ltd.
The polyurethane resin of "WS 5984", "WS 4022", "Superflex 740", "Superflex 150H", "UCOAT UWS-145", "DAOTAN TW-6493", "DAOTAN TW-6490" and "DAOTAN VTW-1262" is a polyurethane urea resin having a urea group.
Examples of commercially available aqueous dispersions of acidic water-dispersible (meth) acrylic resins include: "Mowinyl 6750" (trade name), "Mowinyl 69669 6969D" (trade name), manufactured by Ltd.
In the dispersant, 1 kind or a combination of 2 or more kinds of acidic resins can be used.
The low-molecular-weight amine compound is preferably an amine compound having a molecular weight of 1000 or less, more preferably an amine compound having a molecular weight of 700 or less, still more preferably an amine compound having a molecular weight of 400 or less, and yet more preferably an amine compound having a molecular weight of 300 or less.
The low-molecular amine compound preferably has no repeating unit.
The molecular weight of the low-molecular amine compound is preferably less than the weight average molecular weight of a (meth) acrylic resin ((meth) acrylic resin a) containing at least 1 group selected from the group consisting of a group represented by general formula (1) and a group represented by general formula (2).
As the low-molecular amine compound, ammonia, a primary amine compound, a secondary amine compound, a tertiary amine compound, or the like can be used.
Examples of the primary amine compound include monomethylamine, monoethylamine, monobutylamine, and monoethanolamine.
Examples of the secondary amine compound include dimethylamine, diethylamine, dibutylamine, diethanolamine, diisopropanolamine, and methylpropanolamine.
Examples of the tertiary amine compound include trialkylamines such as trialkylamines having an alkyl group having 1 to 4 carbon atoms exemplified by trimethylamine, triethylamine, and dimethylethylamine; alkanolamines such as dimethylethanolamine, methyldiethanolamine, triethanolamine, triisopropanolamine and the like; heterocyclic amines such as morpholine compounds exemplified by N-alkyl morpholine and N-substituted morpholine compounds, and the like.
The low-molecular-weight amine compound is preferably low in volatility, from the viewpoint that aggregates are not likely to be formed over a long period of time. From this viewpoint, as the low-molecular-weight amine compound, alkanolamines such as monoethanolamine, diethanolamine, diisopropanolamine, methylpropanolamine, dimethylethanolamine, methyldiethanolamine, triethanolamine, triisopropanolamine are preferable.
In the dispersant, 1 kind of low molecular amine compound may be used alone or 2 or more kinds may be used in combination.
The (meth) acrylic resin ((meth) acrylic resin a) may contain a group represented by general formula (1), a group represented by general formula (2), or both of them, containing at least 1 group selected from the group consisting of a group represented by general formula (1) and a group represented by general formula (2). The (meth) acrylic resin a may be, for example, a homopolymer or a copolymer, and is preferably a copolymer.
The weight average molecular weight of the (meth) acrylic resin a is preferably 5000 or more, more preferably 7000 or more. The weight average molecular weight of the (meth) acrylic resin a is preferably 50000 or less, more preferably 30000 or less. The weight average molecular weight of the (meth) acrylic resin A is, for example, preferably 5000 to 500000, more preferably 7000 to 30000.
The (meth) acrylic resin a is preferably dissolved in a nonaqueous solvent contained in the ink, and specifically, when the (meth) acrylic resin a and the nonaqueous solvent contained in the ink are mixed in the same volume at 1 atm and 20 ℃, the (meth) acrylic resin a is preferably uniformly dissolved without being separated into two phases.
The (meth) acrylic resin a preferably contains at least 1 group selected from the group consisting of a group represented by the general formula (1) and a group represented by the general formula (2).
In the general formula (1), R1And R2Each independently represents a hydrogen atom or a substituent, R1And R2Optionally bonded to each other to form a ring.
In the general formula (1), R1And R2Each independently represents a hydrogen atom or a hydrocarbon group optionally having a substituent, or R1And R2Preferably bonded to each other to form a ring.
Examples of the hydrocarbon group include aliphatic hydrocarbon groups such as alkyl groups, alkenyl groups, and alkynyl groups, and the hydrocarbon group may be a straight chain or a branched chain. The number of carbon atoms in the hydrocarbon group is preferably 1 to 8, more preferably 1 to 4. The hydrocarbon group is preferably an alkyl group, preferably an alkyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms. Specific examples of the hydrocarbon group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl and the like. For example, R1And R2Preferably, each independently may be a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms, which may be optionally substituted.
As R1And R2The ring in the case of forming a ring by bonding to each other is preferably a 3-to 8-membered ring, more preferably a 5-to 7-membered ring, and still more preferably a 4-to 6-membered ring. As R1And R2Examples of the rings bonded to each other include: heterocyclic rings containing a nitrogen atom as a heteroatom, heterocyclic rings containing a nitrogen atom and an oxygen atom as heteroatoms, and the like. As R1And R2Examples of the rings bonded to each other include: optionally substituted, morpholine, piperidine, pyrrolidine and the like.
In the general formula (2), R3Represents a substituent group, R4Represents a hydrogen atom or a substituent, R3And R4Optionally bonded to each other to form a ring.
In the general formula (2), R3Represents a hydrocarbon group optionally having a substituent, and R4Represents a hydrogen atom or a hydrocarbon group optionally having a substituent, or preferably R3And R4Bonded to each other to form a ring.
Examples of the hydrocarbon group include aliphatic hydrocarbon groups such as alkyl groups, alkenyl groups, and alkynyl groups, and the hydrocarbon group may be a straight chain or a branched chain. The number of carbon atoms in the hydrocarbon group is preferably 1 to 8, more preferably 1 to 4. The hydrocarbon group is preferably an alkyl group, preferably an alkyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms. Specific examples of the hydrocarbon group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, and the like. For example, R3Preferably, it may be C1 to C optionally having substituents8. More preferably C1-4 alkyl, R4The alkyl group may preferably be a hydrogen atom or an optionally substituted alkyl group having 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms.
As R3And R4The ring in the case of forming a ring by bonding to each other is preferably a 3-to 8-membered ring, more preferably a 5-to 7-membered ring, and still more preferably a 4-to 6-membered ring. As R3And R4Examples of the rings bonded to each other include: heterocyclic rings containing a nitrogen atom as a heteroatom, heterocyclic rings containing a nitrogen atom and an oxygen atom as heteroatoms, and the like. As R3And R4Examples of the ring formed by bonding to each other include a pyrrolidone ring optionally having a substituent.
The (meth) acrylic resin a may contain only 1 kind of group selected from the group consisting of the group represented by the general formula (1) and the group represented by the general formula (2), or may contain 2 or more kinds in combination. For example, the (meth) acrylic resin a may contain only 1 type of group represented by the general formula (1), or may contain 2 or more types in combination. For example, the (meth) acrylic resin a may contain only 1 type of group represented by the general formula (2), or may contain 2 or more types in combination. For example, the (meth) acrylic resin a may contain 1 or more kinds of groups represented by the general formula (1) and/or 1 or more kinds of groups represented by the general formula (2).
The (meth) acrylic resin a preferably has 2 or more groups selected from the group consisting of the group represented by the general formula (1) and the group represented by the general formula (2).
The group represented by the general formula (1) and/or the group represented by the general formula (2) is preferably a carbon atom directly bonded to the main chain of the (meth) acrylic resin a or a carbon atom bonded to the main chain of the (meth) acrylic resin a via a divalent linking group, and more preferably a carbon atom directly bonded to the main chain of the (meth) acrylic resin a. Examples of divalent linking groups include: divalent groups such as alkylene, alkynylene, alkenylene, arylene, heteroarylene, -O-, carbonyl (- (C ═ O) -), carbonyloxy (- (C ═ O) -O-), and groups obtained by combining 2 or more of such divalent groups.
The (meth) acrylic resin a preferably has a β -dicarbonyl group and/or an alkyl group, and more preferably has a β -dicarbonyl group and an alkyl group, from the viewpoints of, for example, improvement of image density, improvement of color development, and reduction of image strike-through. At least 1 group selected from the group consisting of the group represented by the general formula (1) and the group represented by the following general formula (2), β -dicarbonyl, and alkyl group, for example, 2 or 3 thereof, may be contained in the same unit, but it is preferable that at least 1 group selected from the group consisting of the group represented by the general formula (1) and the group represented by the following general formula (2), β -dicarbonyl, and alkyl group are contained in units different from each other.
Examples of the β -dicarbonyl group include β -diketones such as acetoacetyl and propionylacetyl, and β -ketonates such as acetoacetoxy and propionylacetoxy. The (meth) acrylic resin a may contain only 1 or more of these β -dicarbonyl groups.
The alkyl group is preferably an alkyl group having 8 to 22 carbon atoms, more preferably an alkyl group having 12 to 22 carbon atoms. The alkyl group having 8 to 22 carbon atoms may be a straight chain or a branched chain. Specific examples thereof include octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, and docosyl. The (meth) acrylic resin a may contain only 1 or more of these alkyl groups.
The (meth) acrylic resin a may contain an acidic group such as a sulfo group or a carboxyl group.
The (meth) acrylic resin a preferably contains a unit having at least 1 group selected from the group consisting of a group represented by the general formula (1) and a group represented by the general formula (2) (hereinafter, sometimes referred to as "unit Ya").
The (meth) acrylic resin a, for example, more preferably contains: a unit having at least 1 group selected from the group consisting of the group represented by the general formula (1) and the group represented by the general formula (2) ("unit Ya"), a unit having a β -dicarbonyl group (hereinafter, sometimes referred to as "unit Yb"), and/or a unit having an alkyl group (hereinafter, sometimes referred to as "unit Yc"), and further preferably includes the unit Ya, the unit Yb, and the unit Yc.
Examples of the unit (unit Ya) having at least 1 group selected from the group consisting of the group represented by the general formula (1) and the group represented by the general formula (2) include: a unit in which at least 1 group selected from the group consisting of a group represented by the general formula (1) and a group represented by the general formula (2) is directly bonded to a carbon atom of the main chain of the (meth) acrylic resin a, or a unit in which a carbon atom of the main chain of the (meth) acrylic resin a is bonded via a linking group. Examples of such a unit include a unit represented by the following general formula (3) and a unit represented by the following general formula (4).
In the general formula (3), R1And R2Are respectively connected with R in the general formula (1)1And R2Likewise, the preferred ranges are also the same. R5Represents a hydrogen atom or a methyl group. L is1Represents a divalent linking group or a single bond.
In the general formula (4), R3And R4Are respectively connected with R in the general formula (2)3And R4Likewise, the preferred ranges are also the same. R6Represents a hydrogen atom or a methyl group. L is2Represents a divalent linking group or a single bond.
Examples of divalent linking groups include: divalent groups such as alkylene, alkynylene, alkenylene, arylene, heteroarylene, -O-, carbonyl (- (C ═ O) -), carbonyloxy (- (C ═ O) -O-), and groups obtained by combining 2 or more of such divalent groups.
As the unit Ya, for example, a unit derived from a monomer having at least 1 group selected from the group consisting of the group represented by the general formula (1) and the group represented by the general formula (2) (hereinafter, sometimes referred to as "monomer Ya") described later can be used.
The (meth) acrylic resin a may contain only 1 or 2 or more units Ya. The (meth) acrylic resin a may contain, for example, 1 or 2 or more units represented by the general formula (3) and/or 1 or 2 or more units represented by the general formula (4).
The unit having a β -dicarbonyl group (unit Yb) may be, for example, an acrylic acid unit or a methacrylic acid unit.
Examples of the unit Yb include the following: the carbonyl group is bonded to a carbon atom of the main chain, and the β -dicarbonyl group is bonded directly to a carbon atom of the carbonyl group or to a carbon atom of the carbonyl group via a linking group.
As the unit Yb, a unit derived from a (meth) acrylate having a β -dicarbonyl group, a unit derived from a (meth) acrylamide having a β -dicarbonyl group, and the like are preferable. Examples of the (meth) acrylate having a β -dicarbonyl group include, as a preferable example, a β -diketo group or a β -ketonate group having a carbon atom indirectly bonded to a carbonyl group (CO) of an acryloyl group or a methacryloyl group. Examples of the (meth) acrylamide having a β -dicarbonyl group include (meth) acrylamides having a β -diketo group or a β -keto ester group bonded indirectly to a carbon atom of a carbonyl group (CO) of an acryloyl group or a methacryloyl group, as preferred examples. As the unit Yb, for example, a unit derived from a monomer having a β -dicarbonyl group (hereinafter, sometimes referred to as "monomer Yb") described later can be used. The (meth) acrylic resin a may contain only 1 or 2 or more kinds of the unit Yb.
The unit having an alkyl group (unit Yc) may be, for example, an acrylic acid unit or a methacrylic acid unit having an alkyl group.
Examples of the unit Yc include: -COOReA unit wherein the group shown is bonded to a carbon atom of the main chain of the (meth) acrylic resin A, and ReIs an alkyl group (preferably an alkyl group having 8 to 22 carbon atoms, more preferably 12 to 22 carbon atoms). As the unit Yc, for example, a unit derived from a monomer having an alkyl group (hereinafter, sometimes referred to as "monomer Yc") described later can be used.
The (meth) acrylic resin a may contain only 1 or 2 or more units Yc.
The (meth) acrylic resin a may contain other units.
The unit (unit Ya) having at least 1 group selected from the group consisting of the group represented by the general formula (1) and the group represented by the general formula (2) is preferably 5 to 30% by mass, more preferably 10 to 25% by mass or more, based on the whole polymer.
The unit having a β -dicarbonyl group (unit Yb) is preferably 5 to 30% by mass, more preferably 10 to 20% by mass, based on the entire polymer.
The alkyl group-containing unit (unit Yc) is preferably 40 to 90% by mass, more preferably 50 to 90% by mass, and still more preferably 60 to 80% by mass or more of the whole polymer.
Here, the whole polymer is based on all units constituting the (meth) acrylic resin a.
The (meth) acrylic resin a may be, for example, a homopolymer obtained by polymerizing a monomer (monomer Ya) having at least 1 group selected from the group consisting of a group represented by the general formula (1) and a group represented by the general formula (2), a copolymer obtained by polymerizing a monomer mixture containing the monomer Ya, or a derivative of such a homopolymer or copolymer. The monomer mixture preferably comprises: the monomer Ya, the monomer having a β -dicarbonyl group (monomer Yb), and/or the monomer having an alkyl group (monomer Yc), more preferably include the monomer Ya, the monomer Yb, and the monomer Yc.
Examples of the monomer (monomer Ya) having at least 1 group selected from the group consisting of the group represented by the general formula (1) and the group represented by the general formula (2) include a monomer represented by the following general formula (5) and a monomer represented by the following general formula (6).
In the general formula (5), R1And R2Are respectively connected with R in the general formula (1)1And R2Likewise, the preferred ranges are also the same. R5Represents a hydrogen atom or a methyl group. L is1Represents a divalent linking group or a single bond.
In the general formula (6), R3And R4Are respectively connected with R in the general formula (2)3And R4Likewise, the preferred ranges are also the same. R6Represents a hydrogen atom or a methyl group. L is2Represents a divalent linking group or a single bond.
Examples of divalent linking groups include: divalent groups such as alkylene, alkynylene, alkenylene, arylene, heteroarylene, -O-, carbonyl (- (C ═ O) -), carbonyloxy (- (C ═ O) -O-), and groups obtained by combining 2 or more of such divalent groups.
Specific examples of the monomer represented by the general formula (5) or (6) include dimethylacrylamide, acryloylmorpholine, N-vinyl-2-pyrrolidone, and the like.
The monomer having a β -dicarbonyl group (monomer Yb) is preferably a monomer having an acryloyl group or a methacryloyl group and a β -dicarbonyl group, for example. Preferable examples of the monomer Yb include (meth) acrylate having a β -dicarbonyl group and (meth) acrylamide having a β -dicarbonyl group. Specific examples of the monomer Yb include acetoacetoxyalkyl (meth) acrylates such as acetoacetoxyethyl (meth) acrylate, acetoacetoxyalkyl (meth) acrylamides such as hexanedione (meth) acrylate and acetoacetoxyethyl (meth) acrylamide.
The monomer having an alkyl group (monomer Yc) is preferably, for example, a monomer having an acryloyl group or a methacryloyl group and an alkyl group. Examples of the monomer Yc include, for example, alkyl (meth) acrylates and the like, preferably alkyl (meth) acrylates having an alkyl group having 8 to 22 carbon atoms, and more preferably alkyl (meth) acrylates having an alkyl group having 12 to 22 carbon atoms. Specific examples of the monomer Yc include: behenyl (meth) acrylate, lauryl (meth) acrylate (dodecyl (meth) acrylate), and the like.
The monomer mixture may also comprise other monomers.
The amount of each monomer in the monomer mixture may be adjusted so as to be, for example, a preferable ratio of each unit.
These monomers can be polymerized by, for example, known radical polymerization. The reaction system is preferably carried out by solution polymerization or dispersion polymerization. In the polymerization reaction, for example, a polymerization initiator, a chain transfer agent, a polymerization inhibitor, a polymerization accelerator, a dispersant and the like may be added to the reaction system as appropriate. As the polymerization initiator, for example, t-butylperoxy-2-ethylhexanoate and the like can be used. The polymerization solvent (reaction solvent) used in the solution polymerization is not particularly limited, and is preferably a polymerization solvent capable of dispersing and/or dissolving the resin obtained by the polymerization.
In the dispersant, 1 kind of the (meth) acrylic resin a may be used alone, or 2 or more kinds may be used in combination.
The total amount of the acidic resin and the low-molecular amine compound is preferably 10% by mass or more, more preferably 20% by mass or more, and further preferably 30% by mass or more, based on the total amount of the acidic resin, the low-molecular amine compound, and the (meth) acrylic resin a. On the other hand, the total amount of the acidic resin and the low-molecular amine compound is preferably 90% by mass or less, more preferably 80% by mass or less, and still more preferably 70% by mass or less, relative to the total amount of the acidic resin, the low-molecular amine compound, and the (meth) acrylic resin a. The total amount of the acidic resin and the low-molecular amine compound is, for example, preferably 10 to 90 mass%, more preferably 20 to 80 mass%, and still more preferably 30 to 70 mass% of the total amount of the acidic resin, the low-molecular amine compound, and the (meth) acrylic resin a.
The amount of the (meth) acrylic resin a based on the total amount of the acidic resin, the low-molecular amine compound, and the (meth) acrylic resin a is preferably 10% by mass or more, more preferably 20% by mass or more, and still more preferably 30% by mass or more. On the other hand, the amount of the (meth) acrylic resin a relative to the total amount of the acidic resin, the low-molecular amine compound, and the (meth) acrylic resin a is preferably 90% by mass or less, more preferably 80% by mass or less, and still more preferably 70% by mass or less. The amount of the (meth) acrylic resin a relative to the total amount of the acidic resin, the low-molecular amine compound and the (meth) acrylic resin a is, for example, preferably 10 to 90 mass%, more preferably 20 to 80 mass%, and still more preferably 30 to 70 mass%.
The low-molecular amine compound preferably has a molar ratio of a basic group of the low-molecular amine compound to an acidic group of the acidic resin (basic group/acidic group) of 0.5 to 1.5, more preferably 0.8 to 1.2. Here, in the case of using an acidic water-dispersible resin in which the surface of the resin particle is subjected to a surface treatment such as adhesion of an acidic resin particle dispersant, the acidic group of the acidic resin also includes the acidic group of the acidic resin particle dispersant.
The mass ratio of the acid resin to the (meth) acrylic resin a (acid resin (meth) acrylic resin a) is preferably 10: 90-90: 10. more preferably 20: 80-80: 20. further preferably 30: 70-70: 30.
the acidic resin is preferably 0.1 to 20% by mass, more preferably 0.1 to 10% by mass, and still more preferably 0.5 to 10% by mass, based on the total amount of the ink.
The amount of the (meth) acrylic resin a is preferably 0.1 to 10% by mass, more preferably 0.5 to 10% by mass, even more preferably 1 to 5% by mass, and even more preferably 1.5 to 5% by mass, based on the total amount of the ink.
The content of the dispersant is preferably 0.1 mass% or more, more preferably 1 mass% or more, and further preferably 2 mass% or more of the total amount of the acidic resin, the low-molecular-weight amine compound, and the (meth) acrylic resin a, with respect to the total amount of the ink, from the viewpoint of ensuring the dispersibility of the pigment. On the other hand, the content of the dispersant is preferably 20% by mass or less, more preferably 10% by mass or less, and still more preferably 8% by mass or less of the total amount of the acidic resin, the low-molecular-weight amine compound, and the (meth) acrylic resin a, with respect to the total amount of the ink, from the viewpoints of the viscosity of the ink and the storage stability in a high-temperature environment. The content of the dispersant is, for example, preferably 0.1 to 20% by mass, more preferably 1 to 10% by mass, and further preferably 2 to 8% by mass of the total amount of the acidic resin, the low-molecular amine compound, and the (meth) acrylic resin a.
The amount of the dispersant is preferably 0.1 to 5, more preferably 0.1 to 1, in terms of a mass ratio, relative to the pigment 1, as the total amount of the acidic resin, the low-molecular amine compound and the (meth) acrylic resin a.
In the ink, as the nonaqueous solvent, any of a nonpolar organic solvent and a polar organic solvent can be used. These may be used alone, or 2 or more kinds may be used in combination as long as they form a single phase. In the present embodiment, it is preferable to use a water-insoluble organic solvent that does not mix uniformly with water of different volumes at 1 atm and 20 ℃.
The nonpolar organic solvent preferably includes a petroleum hydrocarbon solvent such as an aliphatic hydrocarbon solvent, an alicyclic hydrocarbon solvent, and an aromatic hydrocarbon solvent.
Examples of the aliphatic hydrocarbon solvent and the alicyclic hydrocarbon solvent include nonaqueous solvents such as paraffin type, isoparaffin type, and naphthene type solvents. Preferred examples of commercially available products include: solvent L No. 0, solvent M No. 0, solvent H No. 0, CACTTUS NORMAL PARAFFIN N-10, CACTTUS NORMAL PARAFFIN N-11, CACTTUS NORMAL PARAFFIN N-12, CACTTUS NORMAL PARAFFIN N-13, CACTTUS NORMAL PARAFFIN N-14, CACTTUS NORMAL PARAFFIN N-15H, CACTTUS NORMAL PARAFFIN YHNP, CACTTUS NORMAL PARAFFIN SHNP, Isozole 300, Isozole 400, TECCLEAN N-16, TECCLEAN N-20, TECCLEAN N-22, AF solvent No. 4, AF solvent No. 5, AF solvent No. 6, AF solvent No. 7, Naphthezol 160, Naphthezol 200, Naphzol 220 (all made by JXTG nip & Energy Corporation); isopar G, Isopar H, Isopar L, Isopar M, Exor D40, Exor D60, Exor D80, Exor D95, Exor D110, and Exor D130 (all manufactured by Exxon Mobile Company); MORESCO-WHITE P-40, MORESCO-WHITE P-60, MORESCO-WHITE P-70, MORESCO-WHITE P-80, MORESCO-WHITE P-100, MORESCO-WHITE P-120, MORESCO-WHITE P-150, MORESCO-WHITE P-200, MORESCO-WHITE P-260, MORESCO-WHITE P-350P (all manufactured by MORESCO, Inc.), and the like.
Preferred examples of the aromatic hydrocarbon solvent include Grade alkene L, Grade alkene 200P (both manufactured by JXTG Nippon Oil & Energy Corporation), Solvesso 100, Solvesso 150, Solvesso 200, and Solvesso 200ND (both manufactured by Exxon Mobile Company).
The initial distillation boiling point of the petroleum hydrocarbon solvent is preferably 100 ℃ or higher, more preferably 150 ℃ or higher, and further preferably 200 ℃ or higher. The initial distillation point can be measured according to JIS K0066 "method for testing chemical products by distillation".
The polar organic solvent preferably includes a fatty acid ester solvent, a higher alcohol solvent, a higher fatty acid solvent, and the like.
Examples thereof include: fatty acid ester solvents having 13 or more carbon atoms in 1 molecule, preferably 16 to 30 carbon atoms, such as isononyl isononanoate, isodecyl isononanoate, isotridecyl isononanoate, methyl laurate, isopropyl laurate, hexyl laurate, isopropyl myristate, isopropyl palmitate, hexyl palmitate, isooctyl palmitate, isostearyl palmitate, methyl oleate, ethyl oleate, isopropyl oleate, butyl oleate, hexyl oleate, methyl linoleate, ethyl linoleate, isobutyl linoleate, butyl stearate, hexyl stearate, isooctyl stearate, isopropyl isostearate, 2-octyldecyl tert-valerate, methyl soyate, isobutyl soyate, methyl tall oil, isobutyl tall oil, and the like; higher alcohol solvents having 6 or more carbon atoms, preferably 12 to 20 carbon atoms, in 1 molecule such as isomyristyl alcohol, isopalmitol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, isoeicosyl alcohol, decyltetradecyl alcohol, and the like; and higher fatty acid solvents having 12 or more, preferably 14 to 20, carbon atoms in 1 molecule, such as lauric acid, isomyristic acid, palmitic acid, isopalmitic acid, α -linolenic acid, linoleic acid, oleic acid, and isostearic acid.
The boiling point of the polar organic solvent such as a fatty acid ester solvent, a higher alcohol solvent, or a higher fatty acid solvent is preferably 150 ℃ or higher, more preferably 200 ℃ or higher, and still more preferably 250 ℃ or higher. The non-aqueous solvent having a boiling point of 250 ℃ or higher further includes a non-aqueous solvent not having a boiling point.
The amount of the nonaqueous solvent can be suitably adjusted. The nonaqueous solvent is preferably 60% by mass or more, more preferably 70% by mass or more, based on the total amount of the ink. On the other hand, the amount of the nonaqueous solvent is preferably 99% by mass or less, more preferably 95% by mass or less, with respect to the total amount of the ink. The amount of the nonaqueous solvent is, for example, preferably 60 to 99% by mass, more preferably 70 to 95% by mass, based on the total amount of the ink.
In addition to the above components, the oil-based ink may contain various additives. As the additive, a blowout preventer plugging agent, an antioxidant, a conductivity modifier, a viscosity modifier, a surface tension modifier, an oxygen absorbent, a dye, and the like can be suitably added. The kind of them is not particularly limited, and users in this field can be used.
The amount of water in the ink is preferably 1% by mass or less, more preferably less than 1% by mass, further preferably 0.5% by mass or less, further preferably 0.1% by mass or less, relative to the total amount of the ink.
The total amount of the dispersant and the pigment in the ink is preferably 1 to 40% by mass, more preferably 5 to 30% by mass, based on the total amount of the ink, of the total amount of the pigment, the acidic resin, the low-molecular amine compound, and the (meth) acrylic resin a.
The method for producing the oil-based ink-jet ink is not particularly limited. In the production of the oil-based ink-jet ink, for example, a drying in liquid method is preferably used, and a drying in oil method using a water-in-oil (W/O) emulsion is particularly preferably used.
Examples of a method for producing an oil-based inkjet ink by a water-in-oil emulsion drying method include a method including the steps of: the dispersant is produced by a method of drying in oil using a water-in-oil emulsion. Examples of such a method include a method including the steps of: a step of obtaining a water-in-oil emulsion (hereinafter, also referred to as "step 1") comprising: a continuous phase containing a nonaqueous solvent and a (meth) acrylic resin A, and a dispersed phase containing water, an acidic water-dispersible resin, and a low-molecular amine compound; a step of removing water from the water-in-oil emulsion to obtain a dispersant dispersion containing a dispersant composed of an acidic resin, a low-molecular amine compound and a (meth) acrylic resin a (hereinafter, also referred to as "step 2"); and a step of mixing the dispersant dispersion with the pigment to disperse the pigment (hereinafter, also referred to as "step 3"). In this method, in step 2, a dispersant dispersion can be obtained as a resin particle dispersion in which a dispersant is dispersed as resin particles. However, the method of manufacturing the ink is not limited to this method. The form of the dispersant is also not limited to the resin particles.
This method of drying in oil using a water-in-oil emulsion does not require the use of a volatile organic solvent and is excellent in safety.
The (meth) acrylic resin a has a group represented by the general formula (1) or (2), and therefore, is easily oriented at the interface between the aqueous phase and the oil phase, and is easily formed into an emulsion, and therefore, from this viewpoint, a production method using a water-in-oil (W/O) type emulsion by an in-oil drying method is also preferable.
As the nonaqueous solvent, the (meth) acrylic resin a, the acidic water-dispersible resin, the low-molecular amine compound, and the pigment, those described in the description of the components of the ink can be used. For example, among the water-dispersible resins of the acidic resins described in the description of the components of the ink, the acidic water-dispersible (meth) acrylic resin, the acidic water-dispersible polyurethane resin, and the like are preferable, and the acidic polyurethane urea water-dispersible resin is more preferable.
As the water, tap water, ion-exchanged water, deionized water, or the like can be used.
The water-in-oil emulsion prepared in step 1 may contain other components in the continuous phase and the dispersed phase.
The amount of the acidic water-dispersible resin (solid content) is preferably 1 to 60% by mass, more preferably 10 to 50% by mass, and still more preferably 20 to 40% by mass, based on the total amount of the dispersed phase. The amount of the acidic water-dispersible resin (solid content) is preferably 0.1 to 30% by mass, more preferably 1 to 20% by mass, and still more preferably 5 to 15% by mass, based on the total amount of the water-in-oil emulsion.
The amount of the acidic water-dispersible resin (solid content) is preferably 5% by mass or more, more preferably 10% by mass or more, and still more preferably 14% by mass or more, based on the total amount of the dispersant dispersion obtained in step 2. The amount of the acidic water-dispersible resin (solid content) is preferably 40% by mass or less, more preferably 30% by mass or less, based on the total amount of the dispersant dispersion obtained in step 2. The amount of the acidic water-dispersible resin (solid content) is preferably 5 to 40% by mass, more preferably 10 to 40% by mass, and still more preferably 14 to 30% by mass, based on the total amount of the dispersant dispersion obtained in step 2.
In the water-in-oil emulsion, the amount of the low-molecular amine compound is preferably such that the amount of the basic group thereof is within the above-described preferred molar range with respect to the acidic group of the acidic water-dispersible resin.
The amount of water in the water-in-oil emulsion is preferably 40 to 99% by mass, more preferably 50 to 90% by mass, and still more preferably 60 to 80% by mass, based on the total amount of the dispersed phase. The amount of water is preferably 1 to 50% by mass, more preferably 5 to 50% by mass, and still more preferably 10 to 40% by mass, based on the total amount of the water-in-oil emulsion.
In the water-in-oil emulsion, the amount of the acidic water-dispersible resin (solid content) in the dispersed phase is preferably 20 mass% or more, more preferably 30 mass% or more, further preferably 35 mass% or more, and further preferably 40 mass% or more, relative to the amount of water, from the viewpoint of maintaining the stability of the water-in-oil emulsion in step 1. On the other hand, the amount of water is preferably 80% by mass or less, more preferably 75% by mass or less, of the amount of the acidic water-dispersible resin (solid content) of the dispersed phase relative to the amount of water. In the water-in-oil emulsion, the amount of water, for example, the amount of the acidic water-dispersible resin (solid content) in the dispersed phase is preferably 20 to 80% by mass, more preferably 30 to 80% by mass, further preferably 35 to 80% by mass, and further preferably 40 to 75% by mass, based on the amount of water.
The (meth) acrylic resin a may be used such that the total amount used in the ink is contained in the water-in-oil emulsion obtained in step 1, or may be used such that only a part of the water-in-oil emulsion obtained in step 1 is contained and the remainder is mixed with the pigment and the dispersant dispersion, for example, when the pigment and the dispersant dispersion are mixed in step 3. The (meth) acrylic resin A to be added in step 3 and the like may be the same as or different from the (meth) acrylic resin A contained in the water-in-oil emulsion in step 1.
The amount of the (meth) acrylic resin a in the water-in-oil emulsion is preferably 1 to 60 mass%, more preferably 5 to 50 mass%, and still more preferably 10 to 40 mass% based on the total amount of the continuous phase.
The amount of the (meth) acrylic resin A in the water-in-oil emulsion is preferably 1 to 40% by mass, more preferably 5 to 30% by mass, and still more preferably 10 to 20% by mass, based on the total amount of the water-in-oil emulsion.
The nonaqueous solvent may be used such that the total amount used in the ink is contained in the water-in-oil emulsion obtained in step 1, or may be used such that only a part of the water-in-oil emulsion obtained in step 1 is contained and the rest is mixed with the pigment and the dispersant dispersion, for example, when the pigment and the dispersant dispersion are mixed in step 3. The nonaqueous solvent to be added in step 3 and the like may be the same as or different from the nonaqueous solvent contained in the water-in-oil emulsion in step 1.
In the water-in-oil emulsion, the amount of the nonaqueous solvent is preferably 40 to 99% by mass, more preferably 50 to 95% by mass, and still more preferably 60 to 90% by mass, based on the total amount of the continuous phase.
The amount of the nonaqueous solvent in the water-in-oil emulsion is preferably 30 to 90% by mass, more preferably 40 to 80% by mass, based on the total amount of the water-in-oil emulsion.
In step 1, the method for obtaining the water-in-oil emulsion is not particularly limited.
The water-in-oil emulsion can be produced, for example, as follows: the components of the dispersed phase and the components of the continuous phase are mixed and emulsified to produce the emulsion.
From the viewpoint of improvement in dispersion stability of the ink and improvement in rub resistance resulting therefrom, it is preferable to prepare separately in advance a mixture for a continuous phase containing a component of the continuous phase and a mixture for a dispersed phase containing a component of the dispersed phase. Next, it is preferable to add the mixture for the dispersed phase to the mixture for the continuous phase and perform emulsification treatment. The emulsification treatment can be performed by using an emulsifier such as an ultrasonic homogenizer. The emulsification treatment may be performed, for example, while adding the mixture for the dispersed phase to the mixture for the continuous phase, or may be performed, for example, after adding the mixture for the dispersed phase to the mixture for the continuous phase.
From the viewpoint of reducing the particle diameter of the emulsion, improving the dispersion stability of the resulting ink based thereon, and improving the rub resistance based thereon, for example, the step 1 preferably includes the steps of: a step of obtaining a mixture for a dispersed phase containing an acidic water-dispersible resin, a low-molecular-weight amine compound, and water (hereinafter, also referred to as "step a-1"); a step of obtaining a mixture for a continuous phase comprising a (meth) acrylic resin a and a nonaqueous solvent (hereinafter, also referred to as "step a-2"); and a step of adding the mixture for the dispersed phase to the mixture for the continuous phase to emulsify the mixture (hereinafter, also referred to as "step a-3"). In the step a-1, for example, the acidic water-dispersible resin, the low-molecular amine compound, water, and if necessary, other components may be mixed to obtain a mixture for a dispersed phase. In the step a-2, for example, the (meth) acrylic resin a may be mixed with a nonaqueous solvent and other components as necessary to obtain a mixture for a continuous phase. In the step a-3, the mixture for the dispersed phase obtained in the step a-1 is added to the mixture for the continuous phase obtained in the step a-2, and emulsification is performed. In the step a-3, the emulsification treatment may be performed, for example, while adding the mixture for the dispersed phase to the mixture for the continuous phase, or may be performed after adding the mixture for the dispersed phase to the mixture for the continuous phase. The emulsification treatment can be performed using an emulsifier such as an ultrasonic homogenizer.
In the water-in-oil emulsion, from the viewpoint of improving the production efficiency, it is preferable to mix the components of the continuous phase and the components of the dispersed phase at once and emulsify the obtained mixture by an emulsifier or the like without preparing a mixture for the continuous phase and a mixture for the dispersed phase separately in advance.
From the viewpoint of improving the production efficiency, the step 1 preferably includes, for example, the following steps: a step of mixing an acidic water-dispersible resin, a low-molecular amine compound, water, a (meth) acrylic resin a, and a nonaqueous solvent to obtain a mixture (hereinafter, also referred to as a step "b-1"); and a step of emulsifying the obtained mixture (hereinafter, also referred to as a step "b-2" in some cases). When the dispersed phase and/or continuous phase contains other components, the other components may be mixed together with the acidic water-dispersible resin, the low-molecular amine compound, water, the (meth) acrylic resin a, and the nonaqueous solvent in step b-1. In the step b-2, the emulsification treatment may be performed using an emulsifier such as an ultrasonic homogenizer, for example.
In the step 1, the water-in-oil emulsion preferably has a dispersed phase of 20 to 50 mass% and a continuous phase of 80 to 50 mass% based on the total amount of the water-in-oil emulsion in a mass ratio before removal of water.
In step 2, water is removed from the dispersed phase of the water-in-oil emulsion. Thus, resin particles are formed from the remaining dispersed phase component and the (meth) acrylic resin a of the continuous phase component, and a dispersant dispersion containing a dispersant formed from an acidic resin, a low-molecular amine compound, and the (meth) acrylic resin a in the form of the resin particles can be obtained. In this manner, in step 2, a dispersant dispersion containing a dispersant and a nonaqueous solvent can be obtained. In addition, the (meth) acrylic resin a may be added to the dispersant obtained in step 2, and further, to the dispersant obtained in step 3.
As a method for removing water, for example, reduced pressure, heating, bubbling, addition of a moisture absorbent, or a combination thereof can be used. As the conditions for the pressure reduction and/or heating, there can be adopted: water is removed and the non-aqueous solvent of the continuous phase remains. For the reduced pressure, for example, an evaporator can be used. The heating temperature is preferably 30 ℃ or higher, more preferably 40 to 100 ℃, and further preferably 60 to 90 ℃. For example, it is also preferable to heat the mixture under normal pressure. As the bubbling, it is preferable to promote evaporation by blowing a gas into the liquid and bubbling. Examples of the moisture absorbent include zeolite.
In step 2, the water in the dispersed phase is removed by preferably 80 mass% or more, more preferably 90 mass% or more, further preferably 95 mass% or more, and further preferably 99 mass% or more, based on the amount before removal.
In the dispersant dispersion obtained in step 2, the amount of the solid content of the dispersed phase component of the water-in-oil emulsion relative to the total amount of the dispersant dispersion is preferably 1 to 40% by mass, more preferably 5 to 30% by mass.
In the dispersant dispersion obtained in step 2, the amount of the dispersant is preferably 20 to 60% by mass, more preferably 30 to 50% by mass, based on the total amount of the solid content of the dispersed phase component and the solid content of the continuous phase component of the water-in-oil emulsion.
In step 3, the dispersant dispersion and the pigment are mixed to disperse the pigment.
In step 3, the dispersant dispersion and the pigment are mixed, but if necessary, the (meth) acrylic resin a and/or the nonaqueous solvent may be mixed together with the dispersant dispersion and the pigment as described above. The (meth) acrylic resin A to be added in step 3 and the like may be the same as or different from the (meth) acrylic resin A contained in the water-in-oil emulsion in step 1. The nonaqueous solvent to be added in step 3 and the like may be the same as or different from the nonaqueous solvent contained in the water-in-oil emulsion in step 1.
The amount of each material used in step 3 is not particularly limited, and may be determined as appropriate in consideration of the amount of each component in the ink.
In the step 3, the pigment may be dispersed, for example, while mixing the dispersant dispersion and the pigment, and if necessary, the (meth) acrylic resin a and/or the nonaqueous solvent, and the like, or may be dispersed after mixing the dispersant dispersion and the pigment, and if necessary, the (meth) acrylic resin a and/or the nonaqueous solvent, and the like. A bead mill or the like can be used for dispersion.
The method for producing an oil-based inkjet may further include other steps.
The oil-based inkjet ink can be obtained by mixing the dispersant dispersion and the pigment with, if necessary, the (meth) acrylic resin a and/or a nonaqueous solvent, dispersing the pigment, and if necessary, performing other steps. In the oil-based ink jet ink, the pigment and the dispersant may form colored resin particles, and examples of such colored resin particles include those obtained by coating the dispersant with the pigment.
The average particle diameter of the colored resin particles in the ink is preferably 50 to 300nm, more preferably 80 to 200 nm. The average particle diameter of the colored resin particles in the ink is a volume-based average particle diameter based on a dynamic scattering method, and can be measured, for example, using a dynamic light scattering particle diameter distribution measuring device "nanoparticle analyzer SZ-100" manufactured by horiba ltd.
The printing method using the oil-based inkjet ink is not particularly limited, and may be any of a piezoelectric method, an electrostatic method, a thermal method, and the like. When an inkjet recording apparatus is used, it is preferable that the ink of the present embodiment is ejected from an inkjet head based on a digital signal, and the ejected ink droplets are attached to a recording medium.
The viscosity of the oil-based ink-jet ink varies depending on the nozzle diameter of the ejection head of the ink-jet recording system, the ejection environment, and the like, and the range of suitability thereof is usually preferably 5 to 30mPa · s, more preferably 5 to 15mPa · s, and further preferably about 10mPa · s at 23 ℃.
In the present embodiment, the recording medium is not particularly limited, and the following may be used: and pressure-sensitive adhesive sheets in which a pressure-sensitive adhesive layer is provided on the back surface of a substrate, such as printing paper such as plain paper, coated paper, and specialty paper, cloth, inorganic sheet, film, and OHP sheet. Among them, printing paper such as plain paper and coated paper can be preferably used from the viewpoint of ink permeability.
Here, plain paper refers to paper on which an ink receiving layer, a film layer, and the like are not formed on ordinary paper. Examples of plain paper include high-quality paper, medium-quality paper, paper for PPC, wood pulp paper, recycled paper, and the like. In plain paper, paper fibers having a thickness of several μm to several tens μm form voids of several tens to several hundreds μm, and thus, the paper is easily penetrated by ink.
As the coated paper, coated paper for inkjet, such as matte paper, glossy paper, and semi-glossy paper, so-called coated printing paper, can be preferably used. Here, the coated printing paper is a printing paper conventionally used for letterpress printing, offset printing, gravure printing, and the like, and is a printing paper in which a coating layer is provided on the surface of high-quality paper or medium-quality paper with a coating material containing an inorganic pigment such as clay or calcium carbonate, and a binder such as starch. The paper for coating and printing is classified into micro-coated paper, high-quality light coated paper, medium-quality light coated paper, high-quality coated paper, medium coated paper, art paper, cast coated paper, and the like according to the coating amount of the coating material and the coating method.
A method for producing a dispersant according to 1 embodiment of the present invention is a method for producing a dispersant, including the steps of: a step of obtaining a water-in-oil emulsion (hereinafter, also referred to as "step A") comprising: a continuous phase containing a nonaqueous solvent and a (meth) acrylic resin A, and a dispersed phase containing water, an acidic water-dispersible resin, and a low-molecular amine compound; and a step of removing water from the water-in-oil emulsion (hereinafter, also referred to as "step B").
By the method for producing the dispersant, a dispersant usable in the oil-based inkjet ink can be obtained. However, the method for producing the dispersant for the oil-based inkjet ink is not limited to this method.
The step a is the same as the step 1 described in the above example of the method for producing an oil-based ink-jet ink. In step B, the method of removing water and the amount of water removed are the same as those in step 2 described in the above example of the method of producing an oil-based ink-jet ink.
In the step B, water in the dispersed phase of the water-in-oil emulsion is removed, whereby resin particles are formed from the remaining dispersed phase component and the (meth) acrylic resin a of the continuous phase component, and a dispersant dispersion containing a dispersant comprising an acidic resin, a low-molecular amine compound and the (meth) acrylic resin a in the form of the resin particles can be obtained.
The method for producing the dispersant may further include other steps such as a step of adding the (meth) acrylic resin a.
Examples
The present invention will be described in detail below with reference to examples. The present invention is not limited to the following examples.
The common components are the same in the following examples and comparative examples unless otherwise specified. Unless otherwise specified, "%" represents "% by mass".
The amounts of the respective materials listed in tables 1 to 3 are expressed in parts by mass. The blending amounts of the respective materials described in tables 4 and 5 are expressed in mass%. The amount of each material in tables 1 to 5 is the amount of volatile components contained in the volatile component-containing material.
< materials of ink >
The raw materials of the inks of examples and comparative examples are shown below.
Copper phthalocyanine blue: heliogen Blue D7115F (manufactured by BASF)
Azo lake red: permanent Rubine P-L5b01(Clariant Japan Co., Ltd.)
Carbon black: MOGUL L (manufactured by Cabot Specialty Chemicals)
Aqueous polyurethane urea resin dispersion 1: produced by the following method (aqueous dispersion containing acidic polyurethane urea resin and triethanolamine, active ingredient 30%)
Aqueous polyurethane urea resin dispersion 2: produced by the following method (aqueous dispersion containing acidic polyurethane urea resin and dimethylethanolamine, active ingredient 30%)
Aqueous polyurethane urea resin dispersion 3: produced by the following method (aqueous dispersion containing acidic polyurethane urea resin and triethylamine, active ingredient: 30%)
Aqueous (meth) acrylic resin dispersion 1: the aqueous dispersion (containing the acidic (meth) acrylic resin and dimethylethanolamine, and 30% as an active ingredient) was produced by the following method
Aqueous polyurethane resin dispersion 1: produced by the following method (aqueous dispersion containing acidic polyurethane resin and dimethylethanolamine, active ingredient 30%)
Polyurethane resin solution 1: produced by the following method (solution of acidic polyurethane resin, active ingredient 50%)
Aqueous alkaline polyurethane urea resin dispersion 1: superflex 620 (aqueous dispersion of basic polyurethane urea resin, manufactured by first Industrial pharmaceutical Co., Ltd., active ingredient 30%)
(meth) acrylic resin solution a: (meth) acrylic resin solution, active ingredient 40%, solvent as fatty acid ester solvent)
(meth) acrylic resin solution b: (meth) acrylic resin solution, active ingredient 40%, solvent as fatty acid ester solvent)
(meth) acrylic resin solution c: (meth) acrylic resin solution, active ingredient 40%, solvent as fatty acid ester solvent)
(meth) acrylic resin solution d: (meth) acrylic resin solution, active ingredient 40%, solvent as fatty acid ester solvent)
(meth) acrylic resin solution e: (meth) acrylic resin solution, active ingredient 40%, solvent Petroleum Hydrocarbon solvent)
Acid Polymer 1: solsperse 21000(Nippon Lubrizol Co., manufactured by Ltd.) (effective component 100%)
Fatty acid ester-based solvent 1: isopropyl myristate (Fuji film and Guangdong drug Co., Ltd.)
Petroleum hydrocarbon solvent 1: exor D130 (product of Exxon Mobil Company)
Higher alcohol solvent 1: oleyl alcohol (Fuji film and pure drug Co., Ltd.)
< production of aqueous polyurethane-urea resin dispersions 1 to 3 >
In a four-necked flask, 767.6 parts by mass of polytetramethylene glycol (manufactured by Mitsubishi Chemical Corporation), 55.5 parts by mass of 2, 2-dimethylolbutyric acid (manufactured by Hichem Co., Ltd.), 23.7 parts by mass of 1, 4-butanediol (manufactured by Mitsubishi Chemical Corporation), and 203.2 parts by mass of hexamethylene diisocyanate (manufactured by Tokyo Chemical Co., Ltd.) were reacted at 80 ℃ for 6 hours in 724.4 parts by mass of methyl ethyl ketone (manufactured by Tokyo Chemical Co., Ltd.). Thereafter, 21.8 parts by mass of hexamethylenediamine (manufactured by Tokyo chemical Co., Ltd.) was added thereto. To the solution, 2000 parts by mass of ion-exchanged water at 50 ℃ was added, and the pH was adjusted to 8 with triethanolamine (manufactured by Tokyo chemical Co., Ltd.). Thereafter, the methyl ethyl ketone was removed at 50 ℃ under reduced pressure. Ion-exchanged water was added thereto to adjust the solid content to 30% by mass, thereby obtaining an aqueous triethanolamine dispersion (active ingredient 30%) containing an acidic polyurethaneurea resin and a low-molecular-weight amine compound. This was used as a polyurethane urea resin aqueous dispersion 1.
An aqueous dispersion (active ingredient 30%) containing an acidic polyurethane urea resin and dimethylethanolamine as a low-molecular-weight amine compound was obtained in the same manner as in the production of the polyurethane urea resin aqueous dispersion 1 except that dimethylethanolamine (manufactured by tokyo chemical industry co., ltd.) was used instead of triethanolamine. This was used as a polyurethane urea resin aqueous dispersion 2.
An aqueous dispersion (active ingredient 30%) containing an acidic polyurethane urea resin and triethylamine as a low-molecular-weight amine compound was obtained in the same manner as in the production of the polyurethane urea resin aqueous dispersion 1, except that triethylamine (manufactured by tokyo chemical industry co., ltd.) was used instead of triethanolamine. This was used as a polyurethane urea resin aqueous dispersion 3.
Production of (meth) acrylic resin aqueous Dispersion 1
An emulsified monomer composition was prepared by dissolving 2 parts by mass of EMULGEN 1135S-70 (nonionic non-reactive surfactant, manufactured by kao corporation) and 1.5 parts by mass of Emulsogen EPA073 (anionic non-reactive surfactant, manufactured by Clariant Japan co., ltd.) in 40 parts by mass of ion exchange water, and adding and stirring a monomer mixture a composed of 95 parts by mass of methyl methacrylate (manufactured by tokyo chemical industry co., ltd.) and 5 parts by mass of butyl acrylate (manufactured by tokyo chemical industry co., ltd.). Subsequently, 173 parts by mass of ion-exchanged water and Emulsogen EPA 0731 parts by mass were put into a four-necked flask, and dissolved by stirring, and the temperature was raised to 73 ℃. 5% of the above emulsified monomer composition was charged and stirred, and 1.3 parts by mass of a 3% aqueous solution of potassium persulfate (manufactured by Fuji photo film and Wako pure chemical industries, Ltd.) (hereinafter, may be referred to as "3% potassium persulfate") was added to the mixture to carry out initial polymerization. Thereafter, while maintaining the temperature at 80 ℃ for 3 hours and 30 minutes, 5.3 parts by mass of 3% potassium persulfate and the remaining emulsified monomer composition were added dropwise while carrying out polymerization reaction. After completion of the dropwise addition, the reaction was carried out for 60 minutes to complete the polymerization in the 1 st stage. Subsequently, a monomer mixture B comprising 2.8 parts by mass of methyl methacrylate and 2.4 parts by mass of methacrylic acid (manufactured by Fuji photo film and Wako pure chemical industries, Ltd.) and 0.87 part by mass of 3% potassium persulfate were added simultaneously to start the polymerization in the 2 nd stage. After completion of the dropwise addition, the reaction was aged for 1 hour after adjusting the pH to 8 with dimethylethanolamine (manufactured by Tokyo chemical Co., Ltd.). After cooling to 50 ℃, stirring was continued for 1 hour, and ion-exchanged water was added to adjust the solid content to 30 mass%, thereby obtaining an aqueous dispersion (active ingredient 30%) containing an acidic (meth) acrylic resin and dimethylethanolamine as a low-molecular-weight amine compound. This was used as a (meth) acrylic resin aqueous dispersion 1.
< production of polyurethane resin solution 1 and polyurethane resin aqueous dispersion 1 >
105.1 parts by mass of diethanolamine (manufactured by Fuji film and Wako pure chemical industries, Ltd.) was charged into a four-necked flask, and the temperature was raised to 110 ℃ while stirring with introduction of nitrogen gas. To this, 72.1 parts by mass of acrylic acid (Fuji film and Wako pure chemical industries, Ltd.) was added dropwise over 30 minutes. The Michael addition reaction was terminated at 110 ℃ for 2 hours to obtain a liquid diol. Into another four-necked flask, 35.4 parts by mass of the diol solution obtained above and 15.2 parts by mass of propylene glycol (manufactured by fuji film and mitsubishi corporation) as another diol component were charged, and 0.15 part by mass of dibutyltin dilaurate (manufactured by Tokyo Fine Chemicals co., ltd.) as a tin catalyst was added, and the mixture was stirred with introduction of nitrogen gas, and the temperature was raised to 78 ℃. Then, a mixture of 67.3 parts by mass of hexamethylene diisocyanate (manufactured by Tokyo chemical industry Co., Ltd.) and 118.1 parts by mass of methyl ethyl ketone (manufactured by Tokyo chemical industry Co., Ltd.) was added dropwise over 30 minutes. After the dropwise addition, the reaction mixture was reacted at a reflux temperature of 78 to 80 ℃ for 24 hours, and then cooled to obtain a solution of an acidic polyurethane resin having a solid content of 50 mass%. This was used as a polyurethane resin solution 1.
To 100 parts by mass of the acidic polyurethane resin solution (polyurethane resin solution 1), 80 parts by mass of ion-exchanged water was added, and the pH was adjusted to 8 with dimethylethanolamine (manufactured by tokyo chemical corporation). Thereafter, the methyl ethyl ketone was removed at 50 ℃ and reduced pressure. Ion-exchanged water was added thereto to adjust the solid content to 30% by mass, thereby obtaining an aqueous dispersion (active ingredient 30%) containing an acidic polyurethane resin and dimethylethanolamine as a low-molecular-weight amine compound. This was used as a polyurethane resin aqueous dispersion 1.
Production of (meth) acrylic resin solutions a to f
The (meth) acrylic resin solutions a to f were produced as follows.
Production of (meth) acrylic resin solution a
In a four-necked flask, 200 parts by mass of exocarl M-OL (methyl oleate, manufactured by kao corporation) was charged, and the temperature was raised to 110 ℃ while stirring with introducing nitrogen gas. Subsequently, a mixture of 50 parts by mass of Exceprol M-OL and Perbutyl O (made by Nippon fat Co., Ltd., tert-butyl 2-ethylhexanoate) was added dropwise to 100 parts by mass of a monomer mixture comprising 50 parts by mass of behenyl methacrylate (made by Nippon oil Co., Ltd.), 20 parts by mass of dodecyl methacrylate (made by Kao corporation), 15 parts by mass of acetoacetoxyethyl methacrylate (made by Nippon synthetic chemical Co., Ltd.), and 15 parts by mass of dimethylacrylamide (made by KJ Chemicals Co., Ltd.) while maintaining the temperature at 110 ℃ for 3 hours. After that, the mixture was stirred for 1 hour while keeping the temperature at 110 ℃, then Perbutyl O was added thereto, and the mixture was stirred for 1 hour while keeping the temperature at 110 ℃. Exceprol M-OL was added so that the solid content became 40% by mass, to obtain a (meth) acrylic resin solution a.
Production of (meth) acrylic resin solution b
A (meth) acrylic resin solution b having a solid content of 40 mass% was obtained in the same manner as in the production of the methacrylic resin solution a except that 15 parts by mass of N-vinylpyrrolidone (manufactured by Japan catalyst Co., Ltd.) was used instead of 15 parts by mass of dimethylacrylamide.
Production of (meth) acrylic resin solution c
A (meth) acrylic resin solution c having a solid content of 40 mass% was obtained in the same manner as in the production of the methacrylic resin solution a except that 15 parts by mass of acryloylmorpholine (KJ Chemicals co., ltd.) was used instead of 15 parts by mass of dimethylacrylamide.
Production of (meth) acrylic resin solution d
A (meth) acrylic resin solution d having a solid content of 40 mass% was obtained in the same manner as in the production of the methacrylic resin solution a except that 15 parts by mass of M-90G (methoxypolyethylene glycol #400 methacrylate, produced by Ninghamu chemical industries, Ltd.) was used in place of 15 parts by mass of dimethylacrylamide.
Production of (meth) acrylic resin solution e
A (meth) acrylic resin solution e having a solid content of 40 mass% was obtained in the same manner as in the production of the methacrylic resin solution a except that Exor D130 (product of Exxon Mobile Company, a petroleum hydrocarbon solvent) was used in place of Exceparl M-OL.
Production of (meth) acrylic resin solution f
A (meth) acrylic resin solution f having a solid content of 40 mass% was obtained in the same manner as in the production of the methacrylic resin solution a except that 15 parts by mass of dimethylacrylamide was not used and the amount of acetoacetoxyethyl methacrylate was changed from 15 parts by mass to 30 parts by mass.
< manufacture of ink >
Inks of examples 1 to 11 and comparative examples 1 to 4 were produced as follows.
1. Production of dispersant-containing liquids 1 to 8, 11 to 13
A mixture for a continuous phase (oil phase) was prepared by mixing a non-aqueous solvent with a (meth) acrylic resin solution or an acidic polymer at the compounding amounts shown in EM 1-EM 9 and EM 11-EM 13 in tables 1-3. To the continuous phase mixture thus prepared, aqueous dispersions (polyurethane urea resin aqueous dispersions 1 to 3, (meth) acrylic resin aqueous dispersion 1, or polyurethane resin aqueous dispersion 1) containing the acidic resins described in EM1 to EM9 and EM11 to EM13 in Table 1 to 3 and the low-molecular amine compound as a mixture for a dispersed phase (aqueous phase) were added dropwise while irradiating an Ultrasonic homogenizer "Ultrasonic processor VC-750" (manufactured by SONICS) under ice-cooling for 10 minutes to obtain water-in-oil (W/O) emulsions (EM1 to 9, 11 to 13).
In EM9, since the water phase and the oil phase were separated and no water-in-oil emulsion could be obtained, the following operation was not performed.
The obtained water-in-oil emulsions (EM1 to 8, 11 to 13) were each decompressed in a water bath at 80 ℃ under a vacuum degree of 100hPa using a rotary evaporator "RE 601" (manufactured by yamat CHEMICAL INDUSTRY co., ltd.), and each 100g of the emulsion was treated for 1 hour to remove water from the emulsion, thereby obtaining a dispersant dispersion in the form of a resin particle dispersion having a solid content of 40%. The removal rate of water was substantially 100 mass%. The dispersant dispersions obtained by removing water in this manner using EM1 to 8 and 11 to 13 were used as dispersant-containing liquids 1 to 8 and 11 to 13 (solid content: 40%), respectively (hereinafter, sometimes referred to as dispersants 1 to 8 and 11 to 13, respectively).
2. Production of dispersant-containing liquid 10
The non-aqueous solvent and the (meth) acrylic resin solution a were mixed in the amount indicated by ML10 in table 3. To this solution, a solution of an acidic resin (polyurethane resin solution 1) was added in an amount shown in ML10 in table 3 to obtain a mixed solution. This mixture was referred to as ML 10. This ML10 was subjected to pressure reduction using a rotary evaporator "RE 601" (YAMATO CHEMICAL INDUSTRY co., ltd., product) in a water bath at 60 ℃ under a vacuum of 100hPa to remove methyl ethyl ketone, thereby obtaining a dispersant-containing liquid 10 (solid content 40%) (hereinafter, also referred to as a dispersant 10). In tables 2 and 3, "amount of water in water-in-oil emulsion" indicates amount of water in mixed liquid ML10 for ML 10.
[ Table 1]
[ Table 2]
[ Table 3]
3. Manufacture of ink
The pigment was mixed with a dispersant-containing liquid and a nonaqueous solvent in the compounding amounts shown in tables 4 and 5, and the mixture was subjected to a bead mill "
Dispersion was carried out in Multi LAB (manufactured by Shinmau Enterprises Corporation) to obtain inks of examples 1 to 11 and comparative examples 1, 3 and 4. In comparative example 2, since the pigment was aggregated and the ink could not be obtained, the following evaluation was not performed with respect to comparative example 2.
< evaluation >
The inks of examples 1 to 11 and comparative examples 1, 3 and 4 obtained as described above were evaluated according to the following evaluation methods. The results are shown in tables 4 and 5.
1. Aggregate of carbon black
Ink was introduced into an ink jet printer "ORPHIS GD 9630" (manufactured by Ideal Seikagaku Kogyo Co., Ltd.), and the ink was left for 2 weeks in a state of circulating in an ink passage. 1ml of ink was taken out from the ink passage, observed by an optical microscope, and evaluated for aggregates according to the evaluation criteria described below.
(evaluation criteria)
A: no aggregates were observed
B: aggregates were observed
2. Storage stability
First, the viscosity of the ink immediately after the ink was produced was measured.
Next, the ink was placed in a closed container and left at 70 ℃ for 4 weeks. After that, the ink was sampled and the ink viscosity was measured. The ink viscosity was measured at 23 ℃ using a Rheometer AR-G2(TA Instruments Japan Co., Ltd.) at a cone angle of 2 ℃ and a diameter of 40 mm.
From the viscosity of the ink immediately after the preparation and the viscosity of the ink before and after leaving for 4 weeks, the viscosity change rate was determined according to the following formula, and the storage stability was evaluated by the following criteria. Viscosity change rate (%) - (ink viscosity after leaving for 4 weeks × 100)/(viscosity immediately after preparation) ] -100 (%)
(evaluation criteria)
A: the absolute value of the viscosity change rate is less than 5%
B: the absolute value of the viscosity change rate is more than 5%
3. Abrasion resistance
Each ink was loaded in an ink jet printer "ORPHIS GD 9630" (manufactured by Ideal science and industry Co., Ltd.), and a solid image was printed on plain paper "Ideal paper Multi" (manufactured by Ideal science and industry Co., Ltd.). After 24 hours from printing, a region of the printed matter including a solid image portion having a solid image surface was wiped 5 times within 5 seconds with a white cotton cloth by a Clock meter (CM-1 manufactured by ATLAS ELECTRIC DEVICES COMPANY), and the contamination around the image was evaluated by the following criteria.
(evaluation criteria)
AA: substantially without contamination of the periphery of the image
A: contamination of the periphery of the slightly visible image
B: contamination of the periphery of the visible image
[ Table 4]
[ Table 5]
As shown in the tables, with respect to the inks of the respective examples, no aggregate was observed in the evaluation of aggregates. In contrast, with comparative example 1 using the dispersant 10 not using a low-molecular amine compound, comparative example 3 using the dispersant 11 using an acidic polymer 1 instead of a (meth) acrylic resin containing at least 1 group selected from the group consisting of the group represented by the general formula (1) and the group represented by the general formula (2), and comparative example 4 using the dispersant 13 using a (meth) acrylic resin not containing both the group represented by the general formula (1) and the group represented by the general formula (2), no aggregate was observed in the evaluation of aggregates.
In examples 1 to 3 and 6 to 11 using any one of dispersants 1 to 3 and 6 to 8 using an acidic polyurethane urea resin as an acidic resin, the abrasion resistance was improved.
The inks of examples 1 to 11 all exhibited good storage stability.
Claims (6)
1. An oil-based inkjet ink comprising:
a pigment;
a dispersant formed of an acidic resin, a low-molecular amine compound, and a (meth) acrylic resin containing at least 1 group selected from the group consisting of a group represented by the following general formula (1) and a group represented by the following general formula (2); and the combination of (a) and (b),
a non-aqueous solvent, a solvent selected from the group consisting of,
in the general formula (1), R1And R2Each independently represents a hydrogen atom or a substituent, R1And R2Optionally bonded to each other to form a ring, in the formula (2), R3Represents a substituent group, R4Represents a hydrogen atom or a substituent, R3And R4Optionally bonded to each other to form a ring.
2. The oil-based ink jet ink according to claim 1, wherein the low-molecular amine compound comprises an alkanolamine.
3. The oil-based inkjet ink according to claim 1 or 2, wherein the acidic resin contains at least 1 selected from the group consisting of an acidic (meth) acrylic resin and an acidic polyurethane-based resin.
4. The oil-based inkjet ink according to claim 3, wherein the acidic resin comprises an acidic polyurethaneurea-based resin.
5. A method for producing an oil-based inkjet ink, comprising the steps of:
a step of obtaining a water-in-oil emulsion comprising: a continuous phase containing a nonaqueous solvent and a (meth) acrylic resin containing at least 1 group selected from the group consisting of a group represented by the following general formula (1) and a group represented by the following general formula (2), and a dispersed phase containing water, an acidic water-dispersible resin, and a low-molecular amine compound;
a step of removing water from the water-in-oil emulsion to obtain a dispersant dispersion; and
a step of mixing the dispersant dispersion with a pigment to disperse the pigment,
in the general formula (1), R1And R2Each independently represents a hydrogen atom or a substituent, R1And R2Optionally bonded to each other to form a ring, in the formula (2), R3Represents a substituent group, R4Represents a hydrogen atom or a substituent, R3And R4Optionally bonded to each other to form a ring.
6. A method for producing a dispersant, comprising the steps of:
a step of obtaining a water-in-oil emulsion comprising: a continuous phase containing a nonaqueous solvent and a (meth) acrylic resin containing at least 1 group selected from the group consisting of a group represented by the following general formula (1) and a group represented by the following general formula (2), and a dispersed phase containing water, an acidic water-dispersible resin, and a low-molecular amine compound; and
a step of removing water from the water-in-oil emulsion,
in the general formula (1), R1And R2Each independently represents a hydrogen atom or a substituent, R1And R2Optionally bonded to each other to form a ring, in the formula (2), R3Represents a substituent group, R4Represents a hydrogen atom or a substituent, R3And R4Optionally bonded to each other to form a ring.
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| CN1461781A (en) * | 2002-05-29 | 2003-12-17 | 松下电器产业株式会社 | Ink composite for ink-jet recording, cartridge and recording device |
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| JP2017019998A (en) * | 2015-07-14 | 2017-01-26 | 理想科学工業株式会社 | Water-in-oil type emulsion ink for inkjet |
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| JP7173832B2 (en) * | 2018-03-28 | 2022-11-16 | 理想科学工業株式会社 | Oil-based inkjet ink and method for producing oil-based inkjet ink |
| JP7178919B2 (en) * | 2019-01-30 | 2022-11-28 | 理想科学工業株式会社 | Method for producing oil-based inkjet ink and dispersant |
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| WO2011040174A1 (en) * | 2009-09-30 | 2011-04-07 | 理想科学工業株式会社 | Water-in-oil emulsion type ink for inkjet printing |
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Application publication date: 20210504 |