WO2019123855A1 - Composition de pigment de dioxazine et composition d'encre contenant celle-ci - Google Patents

Composition de pigment de dioxazine et composition d'encre contenant celle-ci Download PDF

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Publication number
WO2019123855A1
WO2019123855A1 PCT/JP2018/040672 JP2018040672W WO2019123855A1 WO 2019123855 A1 WO2019123855 A1 WO 2019123855A1 JP 2018040672 W JP2018040672 W JP 2018040672W WO 2019123855 A1 WO2019123855 A1 WO 2019123855A1
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Prior art keywords
pigment
formula
parts
dioxazine
ether
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PCT/JP2018/040672
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English (en)
Japanese (ja)
Inventor
頌悟 山田
洋匡 菊池
英弘 大竹
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Dic株式会社
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Priority to JP2019517452A priority Critical patent/JP6583586B1/ja
Publication of WO2019123855A1 publication Critical patent/WO2019123855A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B19/00—Oxazine dyes
    • C09B19/02—Bisoxazines prepared from aminoquinones
    • 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
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • 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
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds

Definitions

  • the present invention relates to a dioxazine pigment composition that can be used in a wide range of applications such as printing inks, paints, colored molded articles, and prints.
  • pigments intended for coloring consist of fine particles.
  • a pigment which is an aggregate of fine primary particles
  • a medium as in printing inks and paints such as gravure printing and flexo printing
  • a strong force is applied for a long time to loosen the particles.
  • It is devised such as dispersing or adding a dispersing agent.
  • C.I. I Although the dioxazine pigment represented by CI Pigment Violet 23 is a pigment used in various situations, it tends to cause structural stacking and tends to be strongly aggregated, so it has fluidity when used as a coloring agent in various applications. The problem is remarkable.
  • the present inventors have intensively studied to solve the above-mentioned problems, and as a result, a pigment composition whose fluidity is improved over the prior art by using a plurality of specific dioxazine pigment derivatives in combination with the dioxazine pigment. It has been found that the present invention is obtained.
  • R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a C 1 to C 20 alkyl group, and at least one of R 1 , R 2 , R 3 and R 4 is C 6 to C 4 a pigment derivative represented by a 20 alkyl group, And a dioxazine pigment composition characterized by containing
  • R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom or a C 1 to C 20 alkyl group, and at least one of R 5 , R 6 , R 7 and R 8 is C 6 to C 8 a pigment derivative represented by a 20 alkyl group, Item 2.
  • any two of R 1 , R 2 , R 3 and R 4 are a C 6 to C 20 alkyl group, and any two of them are a methyl group.
  • any two of R 1 , R 2 , R 3 and R 4 are a C 6 to C 20 alkyl group, and any two of them are a methyl group
  • Item 7 Per 100 parts by mass of dioxazine pigment, Item 2.
  • the pigment derivative represented by the formula (I) is 0.1 parts by mass or more and 10.0 parts by mass or less, The pigment derivative represented by the formula (II) is contained in an amount of 0.1 parts by mass or more and 10.0 parts by mass or less, provided that the pigment derivative represented by the formula (I) and the pigment derivative represented by the formula (II) The total amount of with is 10.0 parts by mass or less, Item 3.
  • Item 9 An ink composition comprising at least the dioxazine pigment composition according to any one of items 1 to 8, a nitrocellulose resin, and a glycol ether solvent.
  • Item 10 The ink composition according to claim 9, wherein the glycol ether solvent is a monoether or diether of ethylene glycol or propylene glycol.
  • a dioxazine pigment composition excellent in fluidity (initial viscosity, viscosity over time) can be provided.
  • R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a C 1 to C 20 alkyl group, and at least one of R 1 , R 2 , R 3 and R 4 is A pigment derivative represented by a C 6 -C 20 alkyl group]
  • a dioxazine pigment composition comprising:
  • Such a pigment composition of the present invention exhibits excellent fluidity even when used as a printing ink or paint. Furthermore, the pigment composition of the present invention exhibits excellent fluidity even in glycol ether-based inks, which have recently been required by the market.
  • the fluidity refers to the initial viscosity and the viscosity over time when the ink is prepared.
  • the dioxazine pigment used in the present invention is C. I. Pigment violet 23, C.I. I. Pigment violet 37, C.I. I. Pigment blue 80 and the like.
  • C.I. I. Pigment Violet 23 represented by the following chemical structural formula
  • Such C.I. I. Pigment Violet 23 may be a commercially available product (for example, FASTOGEN SUPER VIOLET series (specific surface area by BET method from DIC Corporation: 50 to 120 m 2 / g), etc. may be used, or a publicly known and commonly used method. You may manufacture and use.
  • R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a C 1 to C 20 alkyl group, and at least one of R 1 , R 2 , R 3 and R 4 is C 6 to C 20 alkyl group.
  • C 1 to C 20 alkyl group refers to methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl Groups, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group and the like.
  • the “C 6 to C 20 alkyl group” that at least one of R 1 , R 2 , R 3 and R 4 can have is a hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group And tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group and the like, but from the viewpoint of improving fluidity, alkyl groups of C 8 to C 18 are preferable, C 10 and more preferably an alkyl group ⁇ C 15.
  • R 1 , R 2 , R 3 and R 4 be “C 6 to C 20 alkyl groups”, and “C Examples of the 6 to C 20 alkyl group "include those described above.
  • the remaining one to three Rs are a hydrogen atom or C 1 to
  • the C 20 alkyl group is preferably a C 1 to C 3 alkyl group from the viewpoint of further enhancing the fluidity.
  • Particularly excellent effects are obtained when any two of R 1 , R 2 , R 3 and R 4 are C 6 -C 20 alkyl groups and any two of them are methyl groups.
  • the effects of the present invention can be obtained even if all of R 1 , R 2 , R 3 and R 4 are “C 6 to C 20 alkyl groups”.
  • R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom or a C 1 to C 20 alkyl group, and at least one of R 5 , R 6 , R 7 and R 8 is C 6 to C 20 alkyl group.
  • the groups represented by two (SO 3 NR 5 R 6 R 7 R 8 ) in the formula (II) may be the same or different, but are preferably the same from the industrial viewpoint.
  • C 1 to C 20 alkyl group refers to methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl Groups, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group and the like.
  • the “C 6 to C 20 alkyl group” that at least one of R 5 , R 6 , R 7 and R 8 can have is a hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group And tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group and the like, but from the viewpoint of improving fluidity, alkyl groups of C 8 to C 18 are preferable, C 10 and more preferably an alkyl group ⁇ C 15.
  • R 5 , R 6 , R 7 and R 8 be “C 6 to C 20 alkyl groups”, and “C Examples of the 6 to C 20 alkyl group "include those described above.
  • the remaining one to three Rs are a hydrogen atom or C 1 to
  • the C 20 alkyl group is preferably a C 1 to C 3 alkyl group from the viewpoint of further enhancing the fluidity.
  • the effects of the present invention can be obtained even if all of R 5 , R 6 , R 7 and R 8 are “C 6 to C 20 alkyl groups”.
  • the present invention is represented by a group represented by (SO 3 H) and (SO 3 NR 1 R 2 R 3 R 4 ) with respect to a dioxazine pigment residue by trial and error among derivatives considered innumerably.
  • a pigment derivative represented by the above-mentioned formula (I) The groups (R 5 , R 6 , R 7 and R 8 ) represented by (SO 3 NR 5 R 6 R 7 R 8 ) for the dioxazine pigment residue are as described above, and at least one of them is as described above.
  • both of the pigment derivatives represented by the formula (II) in which two R's are C 6 to C 20 alkyl groups are present together with the dioxazine pigment extremely superior fluidity is achieved as compared to the prior art
  • the pigment composition can be obtained.
  • the action mechanism is not clear because the present invention is found by trial and error, but the group represented by (SO 3 H) in the pigment derivative represented by the formula (I) has wettability.
  • the pigment derivative represented by the formula (II) contributes to the increase in steric hindrance among the pigments.
  • the stability after ink preparation in a nitrocellulose ink (hereinafter sometimes referred to as NC ink) is improved, and a low viscosity is maintained even after a storage stability test.
  • NC ink nitrocellulose ink
  • the pigment derivative represented by the formula (I) and the formula are more preferable because glycol ether solvents such as ethoxypropanol constituting the NC ink are more hydrophobic than ethanol and the like constituting the ink widely used conventionally.
  • the alkyl chain moiety of the pigment derivative represented by (II) is more extended in the glycol ether solvent, and it is considered that the repulsive effect by steric hindrance is large. Therefore, it is considered that the glycol ether-based ink, the market demand of which has been increasing in recent years, exhibits a higher effect.
  • the present invention is an invention which is different from the prior art such as Patent Document 1 in that a pigment derivative partially having a sulfo group is also used in combination.
  • the pigment composition of the present invention can further obtain the effect of the present invention by having a derivative of the formula (III) in addition to the above two pigment derivatives. According to the combined effect of the three pigment derivatives described so far, it is expected that a further reduction effect of the ink viscosity can be expected particularly in an ink composition using a nitrocellulose resin (sometimes referred to as NC resin herein). Conceivable.
  • the pigment derivative represented by Formula (I) can be contained in 0.1 parts by mass or more and 10.0 parts by mass or less with respect to 100 parts by mass of the dioxazine pigment.
  • the pigment derivative represented by the formula (I) is 100 parts by mass of the dioxazine pigment.
  • the pigment derivative represented by the formula (II) can be contained in an amount of 0.1 parts by mass or more and 10.0 parts by mass or less and 0.1 parts by mass or more and 10.0 parts by mass or less (however, in formula (I) The total amount of the pigment derivative represented and the pigment derivative represented by formula (II) is 10.0 parts by mass or less). It is considered that the ink viscosity reduction effect is further enhanced by using such a blending amount.
  • each pigment derivative is shown. Either method may be adopted.
  • a dioxazine pigment sulfonic acid derivative (C.I. Direct Blue 108) manufactured by a commercially available method or a commonly used method can be used.
  • a dioxazine known as a commonly used method Dioxazine pigment sulfonic acid derivatives can be prepared by sulfonation of the pigments with concentrated sulfuric acid or oleum, or by sulfochlorination of the above starting materials with chlorosulfonic acid followed by hydrolysis with water.
  • the desired derivative is obtained by mixing the amine in the homogeneous or heterogeneous phase of the water or organic solvent of the dioxazine pigment sulfonic acid derivative.
  • a dioxazine pigment sulfonic acid derivative having only 2 sulfo group substituents is used as a raw material
  • an amine having 1 mol or less per 2 moles of sulfo group of the dioxazine pigment sulfonic acid derivative is used to form a compound of formula (I)
  • the pigment derivatives represented can be prepared.
  • pigment derivatives represented by Formula (I) and Formula (II) can be simultaneously produced by using 1 to 2 moles of an amine.
  • the pigment derivative of Formula (II) can be manufactured by using an amine of 2 mol or more with respect to 2 mol of sulfo groups of a dioxazine pigment sulfonic acid derivative.
  • a dioxazine pigment sulfonic acid derivative having a distribution of 1 to 5 substituents of sulfo group can also be used for producing each pigment derivative.
  • the second sulfo group of the derivative having 2 substituents and the second sulfo group of the derivative having 3 substituents become the ammonium salt (ie, the pigment derivative represented by the formula (II) is synthesized)
  • the third sulfo group of the derivative having 3 substituents is an ammonium salt.
  • a dry powder or wet cake of the dioxazine pigment is added to water or an organic solvent and stirred to make a dioxazine pigment slurry.
  • the pigment composition of the present invention can also be produced by mixing a dry powder of a pigment derivative and a dry powder of a dioxazine pigment. That is, the pigment derivative prepared by the method for producing the pigment derivative is mixed with the dry powder of the dioxazine pigment at an appropriate ratio such that the desired ratio of the pigment derivative represented by the formulas (I) to (II) can be obtained.
  • the pigment composition of the present invention can be easily produced.
  • the pigment composition of the present invention can be further adjusted to be suitable for each application by further containing an additive, a dispersant and the like as long as the effect of the present invention is not adversely affected.
  • the pigment composition of this invention can also be used together and used organic pigments other than a dioxazine pigment as a coloring component.
  • Organic pigments that can be used in combination can be selected appropriately from among known organic pigments in accordance with various uses.
  • the pigment composition of the present invention thus obtained can be suitably used in any application requiring a coloring function.
  • it can be used in various conventional applications such as paints, printing inks, colored molded articles, toners for electrostatic charge image development, color filters for liquid crystal display devices, aqueous inks for inkjet recording, and the like.
  • the pigment composition of the present invention can provide a printing ink excellent in initial viscosity and storage stability.
  • the printing ink can be prepared by mixing various known binder resins, various solvents, various additives and the like with the pigment composition of the present invention according to the conventional preparation method.
  • a liquid ink can be prepared by adjusting a base ink for liquid ink having a high pigment concentration and using various binders, various solvents, various additives, and the like.
  • the pigment composition of the present invention can produce PU ink and NC ink excellent in initial viscosity and storage stability, and is suitable as an organic pigment composition for gravure printing ink and flexographic printing ink.
  • the PU ink comprises a PU resin, a pigment, a solvent and various additives
  • the NC ink comprises an NC resin, a pigment, a solvent and various additives.
  • the PU resin is not particularly limited as long as it has a urethane structure in the skeleton, and includes polyurethane, polyurethane polyurea and the like.
  • Aromatic organic solvents such as toluene and xylene; Ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, Ester solvents such as ethyl acetate, n-propyl acetate, isopropyl acetate, isobutyl acetate, etc.
  • Alcohol solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol and t-butanol
  • Ethylene glycol monomethyl ether ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-i-propyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-i-butyl ether, ethylene glycol mono-t -Butyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-i-propyl ether, propylene glycol mono-n-butyl ether, propylene glycol mono-i-butyl ether, propylene glycol Mono-t-butyl ether, ethylene glycol dimethyl ether, ethylene glyco
  • the pigment composition of the present invention exhibits excellent fluidity to inks composed of any of the solvents, but in order to extensively describe the applicability to glycol ether-based inks, the market demand for which has increased in recent years. Do.
  • glycol ether ink a low drying speed ink containing a glycol ether solvent as a main component
  • the glycol ether-based ink has lower volatility than the conventional alcohol-based ink, and is expected to improve the leveling property (high definition) of the surface of the printed material as the drying speed is reduced.
  • leveling property high definition
  • viscosity initial viscosity, temporal viscosity
  • ink properties of glycol ether-based inks but the flowability improvement of dioxazine pigments similar to conventional alcohol-based inks Even with the use of technology, it has become clear that sufficient liquidity can not be ensured.
  • an ink composition of the present invention contains at least a pigment composition of the present invention and a glycol ether solvent.
  • glycol ether solvents ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether are preferable, and propylene glycol monoethyl ether is preferable.
  • Ether is more preferred.
  • the solvents may be used alone or in combination of two or more.
  • surfactants such as anionic, nonionic, cationic and amphoteric surfactants, gum rosin, polymerized rosin, disproportionated rosin, hydrogenated rosin, hydrogenated rosin, hardened rosin, hardened rosin, alkyd phthalate resin, etc.
  • Rosins, pigment derivatives, dispersants, wetting agents, adhesion aids, leveling agents, antifoaming agents, antistatic agents, trapping agents, antiblocking agents, wax components and the like can be used.
  • the pigment composition of the present invention exhibits excellent fluidity to inks composed of any resin, but is useful in nitrocellulose.
  • Nitrocellulose is also called nitrification cotton, and is a resin in which the hydroxyl group of cellulose is nitrated with a mixed acid of sulfuric acid and nitric acid.
  • the solubility of nitrocellulose in a solvent changes depending on the degree of nitration, and those with high degree of nitrification are used as hydrocarbon solvents and ester solvents, and those with low degree of nitrification are used as alcohol solvents.
  • Nitrocellulose has a high glass transition point, and there is almost no blocking when winding up a printed matter. Furthermore, nitrocellulose is widely used as a binder resin for printing inks, since nitrocellulose-based gravure inks have good printability.
  • the printing ink using the pigment composition of the present invention prepared as described above may be diluted in ethyl acetate, polyurethane varnish, or polyamide varnish. it can.
  • a well-known and usual method can be employ
  • the pigment composition of the present invention is used as a paint as a coloring agent
  • various resins such as acrylic resin, melamine resin, epoxy resin, polyester resin, polyurethane resin, polyamide resin and phenol resin are used as the paint.
  • solvents used for paints aromatic solvents, acetic acid ester solvents, propionate solvents, alcohol solvents, ether solvents, ketone solvents, aliphatic hydrocarbon solvents, nitrogen compound solvents, lactone solvents Carbamates such as a 48: 52 mixture of methyl carbamate and ethyl carbamate, water, and the like.
  • polar solvents such as propionate type, alcohol type, ether type, ketone type, nitrogen compound type, lactone type, water and the like and soluble in water are suitable.
  • a pigment additive and / or a pigment composition is dispersed or mixed in a liquid resin to form a resin composition for a paint
  • conventional additives such as dispersants, fillers, and paints are prepared.
  • Auxiliary agents, desiccants, plasticizers and / or auxiliary pigments can be used. This is accomplished by dispersing or mixing each component, alone or several together, collecting all the components, or adding all of them at once.
  • a disperser for dispersing the composition containing the pigment composition prepared according to the application as described above a disperser, homomixer, paint conditioner, scandex, bead mill, attritor, ball mill, two rolls, three rolls
  • a known dispersing machine such as a roll and a pressure kneader can be mentioned, it is not limited thereto.
  • a resin and a solvent are added and dispersed such that the viscosity of the pigment composition can be dispersed by the disperser.
  • the high concentration paint base after dispersion has a solid content of 5 to 20%, to which a resin and a solvent are further mixed to be used as a paint.
  • Example 1 C. I. 171.9 parts (60 parts of pigment part) of CI Pigment Violet 23 (manufactured by DIC Corporation) and 828.1 parts of ion-exchanged water are put in a 2 L stainless steel cup, and the homodisper 2.5 type (rotational speed 500 rpm) C.) for 30 minutes. I. A slurry of pigment violet 23 was prepared. 2) Apart from this, C.I. C.I. having an average number of sulfo groups of 2.4 (the main component is 2). I.
  • Ion-exchanged water is added to a wet cake of pigment violet 23 sulfonic acid derivative (made by DIC Corporation) (3.0 parts of dyestuff) to make a total of 50 parts, and it is brought to 60 ° C. using a magnetic stirrer in a 100 mL glass beaker. C., while heating and stirring for 1 hour.
  • a sulfonic acid derivative slurry of pigment violet 23 was prepared.
  • Ion-exchanged water is added to a wet cake of pigment violet 23 sulfonic acid derivative (made by DIC Corporation) (3.0 parts of dyestuff) to make a total of 50 parts, and it is brought to 60 ° C. using a magnetic stirrer in a 100 mL glass beaker. C., while heating and stirring for 1 hour.
  • a sulfonic acid derivative slurry of pigment violet 23 was prepared.
  • Preparation Example 1 (Preparation of NC glycol ether varnish) 164.5 parts of nitrocellulose resin (nitrogen content: 10.7 to 12.2, nonvolatile content 70%, volatile content isopropanol), 335.5 parts of propylene glycol monoethyl ether (manufactured by Wako Pure Chemical Industries, Ltd.) in 1 L poly The mixture was placed in a bottle and dispersed for 2 hours with a paint shaker (manufactured by Toyo Seiki Seisakusho Co., Ltd.) to obtain an NC glycol ether varnish.
  • nitrocellulose resin nitrogen content: 10.7 to 12.2, nonvolatile content 70%, volatile content isopropanol
  • propylene glycol monoethyl ether manufactured by Wako Pure Chemical Industries, Ltd.
  • Preparation Example 2 (Preparation of NC ethanol varnish) Nitrocellulose resin (nitrogen content: 10.7 to 12.2, nonvolatile content 70%, volatile content ethanol) 164.5 parts, ethanol (Wako Pure Chemical Industries, Ltd. 436.5 parts, ethyl acetate (Wako Pure Chemical Industries, Ltd.) 13.5 parts of Industrial Co., Ltd. was put into a 1 L poly bottle and dispersed for 2 hours with a paint shaker (manufactured by Toyo Seiki Seisakusho Co., Ltd.) to obtain NC ethanol varnish.
  • a paint shaker manufactured by Toyo Seiki Seisakusho Co., Ltd.
  • Example 2 18.2 parts of dioxazine pigment composition (1), 32.5 parts of NC glycol ether varnish, 40.3 parts of propylene glycol monoethyl ether (manufactured by Wako Pure Chemical Industries, Ltd.), n-propanol (Wako Pure Chemical Industries, Ltd. 9.0 parts, 150 parts of SAZ beads (Zirconia YTZ ball 1.25 ⁇ , made by Tokyo Glass Instruments Co., Ltd.) in a 200 mL glass bottle, and 2 by Shaker Skandex SK550 (made by Fast & Fluid Management B. V. Company) Time dispersion was carried out to obtain an ink composition (1).
  • SAZ beads Zirconia YTZ ball 1.25 ⁇ , made by Tokyo Glass Instruments Co., Ltd.
  • Shaker Skandex SK550 made by Fast & Fluid Management B. V. Company
  • Example 2 18.2 parts of dioxazine pigment composition (2), 32.5 parts of NC glycol ether varnish, 40.3 parts of propylene glycol monoethyl ether (manufactured by Wako Pure Chemical Industries, Ltd.), n-propanol (Wako Pure Chemical Industries, Ltd. 9.0 parts, 150 parts of SAZ beads (Zirconia YTZ ball 1.25 ⁇ , made by Tokyo Glass Instruments Co., Ltd.) in a 200 mL glass bottle, and 2 by Shaker Skandex SK550 (made by Fast & Fluid Management B. V. Company) Time dispersion was carried out to obtain an ink composition (2).
  • SAZ beads Zirconia YTZ ball 1.25 ⁇ , made by Tokyo Glass Instruments Co., Ltd.
  • Shaker Skandex SK550 made by Fast & Fluid Management B. V. Company
  • Example 4 Dioxazine pigment composition (1) 22.0 parts, NC ethanol varnish 36.9 parts, ethanol (manufactured by Wako Pure Chemical Industries, Ltd.) 36.9 parts, ethyl acetate (manufactured by Wako Pure Chemical Industries, Ltd.) 1.1 parts 150 parts of SAZ beads (Zirconia YTZ ball 1.25 ⁇ , manufactured by Tokyo Glass Instruments Co., Ltd.) in a 200 mL glass bottle, and dispersed for 2 hours with Shaker Skandex SK550 (manufactured by Fast & Fluid Management B. V. Company), and ink composition I got the thing (3). Comparative Example 2 Untreated C.I. I.
  • Pigment Violet 23 (manufactured by DIC Corporation), 18.2 parts, NC ethoxypropanol varnish 32.5 parts, propylene glycol monoethyl ether (manufactured by Wako Pure Chemical Industries, Ltd.) 40.3 parts, n-propanol (Wako Pure Chemical Industries, Ltd. 9.0 parts of made by Co., Ltd., 150 parts of SAZ beads (zirconia YTZ ball, 1.25 ⁇ , made by Tokyo Glass Instruments Co., Ltd.) in a 200 mL glass bottle and put in Shaker Skandex SK550 (made by Fast & Fluid Management B. V. Company) The mixture was dispersed for 2 hours to obtain a comparative ink composition (1 ').
  • SAZ beads zirconia YTZ ball, 1.25 ⁇ , made by Tokyo Glass Instruments Co., Ltd.
  • Shaker Skandex SK550 made by Fast & Fluid Management B. V. Company
  • Comparative Example 3 Comparative Dioxazine pigment composition (3 ′) 22.0 parts, NC ethanol varnish 36.9 parts, ethanol (Wako Pure Chemical Industries, Ltd. 36.9 parts), ethyl acetate (Wako Pure Chemical Industries, Ltd.) 1.
  • One part, 150 parts of SAZ beads (Zirconia YTZ ball 1.25 ⁇ , manufactured by Tokyo Glass Instruments Co., Ltd.) are put in a 200 mL glass bottle, and dispersed for 2 hours with Shaker Skandex SK550 (manufactured by Fast & Fluid Management B. V. Company), The comparative ink composition (2 ') was obtained.
  • Comparative Example 4 Untreated C.I. I.
  • Pigment Violet 23 (manufactured by DIC Corporation), 36.9 parts of NC ethanol varnish, 36.9 parts of ethanol (manufactured by Wako Pure Chemical Industries, Ltd.), ethyl acetate (manufactured by Wako Pure Chemical Industries, Ltd.) 1.
  • 150 parts of SAZ beads Zirconia YTZ ball 1.25 ⁇ , manufactured by Tokyo Glass Instruments Co., Ltd.
  • Shaker Skandex SK550 manufactured by Fast & Fluid Management B. V. Company

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  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

Le problème à résoudre par la présente invention est de fournir une composition de pigment de dioxazine ayant une fluidité remarquablement améliorée. Le problème est résolu avec une composition de pigment de dioxazine caractérisée en ce qu'elle comprend un pigment de dioxazine et un dérivé de pigment représenté par la formule (I) [dans laquelle R1, R2, R3 et R4 représentent chacun indépendamment un atome d'hydrogène ou un groupe alkyle en C1-20, au moins l'un de R1, R2, R3 et R4 étant un groupe alkyle en C6-20].
PCT/JP2018/040672 2017-12-21 2018-11-01 Composition de pigment de dioxazine et composition d'encre contenant celle-ci WO2019123855A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60124657A (ja) * 1983-12-09 1985-07-03 Toyo Ink Mfg Co Ltd アゾ顔料組成物
JPH07292305A (ja) * 1994-04-22 1995-11-07 Toyo Ink Mfg Co Ltd オフセットインキ組成物
JP2005173459A (ja) * 2003-12-15 2005-06-30 Sanyo Shikiso Kk カラーフィルタ用着色組成物
JP2009029858A (ja) * 2007-07-25 2009-02-12 Toyo Ink Mfg Co Ltd バイオレット顔料の製造方法
WO2013087376A1 (fr) * 2011-12-14 2013-06-20 Agfa Graphics Nv Pigments modifiés en surface et encres non aqueuses les renfermant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60124657A (ja) * 1983-12-09 1985-07-03 Toyo Ink Mfg Co Ltd アゾ顔料組成物
JPH07292305A (ja) * 1994-04-22 1995-11-07 Toyo Ink Mfg Co Ltd オフセットインキ組成物
JP2005173459A (ja) * 2003-12-15 2005-06-30 Sanyo Shikiso Kk カラーフィルタ用着色組成物
JP2009029858A (ja) * 2007-07-25 2009-02-12 Toyo Ink Mfg Co Ltd バイオレット顔料の製造方法
WO2013087376A1 (fr) * 2011-12-14 2013-06-20 Agfa Graphics Nv Pigments modifiés en surface et encres non aqueuses les renfermant

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