WO2019124050A1 - Composition de pigment phtalocyanine de cuivre et composition d'encre la contenant - Google Patents

Composition de pigment phtalocyanine de cuivre et composition d'encre la contenant Download PDF

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Publication number
WO2019124050A1
WO2019124050A1 PCT/JP2018/044512 JP2018044512W WO2019124050A1 WO 2019124050 A1 WO2019124050 A1 WO 2019124050A1 JP 2018044512 W JP2018044512 W JP 2018044512W WO 2019124050 A1 WO2019124050 A1 WO 2019124050A1
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copper phthalocyanine
parts
formula
pigment
group
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PCT/JP2018/044512
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English (en)
Japanese (ja)
Inventor
晋吾 斎藤
太一 橋口
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Dic株式会社
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Priority to JP2019545380A priority Critical patent/JP6631764B2/ja
Publication of WO2019124050A1 publication Critical patent/WO2019124050A1/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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/009—Non common dispersing agents polymeric dispersing agent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0002—Grinding; Milling with solid grinding or milling assistants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0025—Crystal modifications; Special X-ray patterns
    • C09B67/0026—Crystal modifications; Special X-ray patterns of phthalocyanine pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C09B67/0035—Mixtures of phthalocyanines
    • 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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds

Definitions

  • the present invention relates to a copper phthalocyanine 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, in a medium, as in printing inks and paints such as gravure printing and flexo printing, for example, a strong force is applied for a long time to loosen the particles.
  • It is devised such as dispersing or adding a dispersing agent.
  • copper phthalocyanine pigments are pigments used in various situations, but when used as a coloring agent in various applications, problems concerning fluidity are remarkable.
  • the ink properties of the glycol ether ink include viscosity (initial viscosity, viscosity over time), and printability includes resolubility.
  • Patent Document 1 discloses a method of treating a copper phthalocyanine sulfonic acid ammonium salt (primary to quaternary) in printing ink and paint applications in order to improve the viscosity aptitude of the copper phthalocyanine pigment composition.
  • the present inventors have found that the viscosity of a glycol ether-based ink is obtained by using a plurality of specific copper phthalocyanine sulfonic acid derivatives in combination with a copper phthalocyanine pigment. It has been found that a pigment composition sufficiently low and compatible with the ink can be obtained, and the present invention has been completed.
  • 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 C 6 -C 20 alkyl group
  • the copper phthalocyanine pigment composition (Hereinafter, it may be described with the pigment composition of this invention.) Characterized by the above-mentioned.
  • 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 C 6 -C 20 alkyl group]
  • 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 A copper phthalocyanine pigment composition (hereinafter sometimes referred to as a pigment composition of the present invention), which is a C 6 to C 20 alkyl group].
  • Item 3 The copper phthalocyanine pigment composition according to Item 1, wherein any two of R 1 , R 2 , R 3 and R 4 in the formula (I) are a C 6 to C 20 alkyl group.
  • Item 4 In the above formula (I), any two of R 1 , R 2 , R 3 and R 4 are a C 6 to C 20 alkyl group, and the above formulas (II): R 5 , R 6 , R 7 and The copper phthalocyanine pigment composition according to Item 2, wherein any two of R 8 are a C 6 to C 20 alkyl group.
  • Item 5 With respect to 100 parts by mass of ⁇ -type copper phthalocyanine pigment, Item 4. The copper phthalocyanine pigment composition according to Item 1 or 3, wherein the pigment derivative represented by Formula (I) is contained in an amount of 0.1 parts by mass or more and 10.0 parts by mass or less. Item 6.
  • 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 5.
  • Item 8 An ink composition comprising at least the pigment composition according to any one of Items 1 to 7, a nitrocellulose resin, and a glycol ether solvent. ].
  • a copper phthalocyanine pigment composition having good viscosity suitability (initial viscosity, temporal viscosity) and excellent re-solubility in a glycol ether ink.
  • the present invention relates to a ⁇ -type copper phthalocyanine pigment, Formula (I):
  • 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 And a pigment derivative represented by the C 6 -C 20 alkyl group].
  • a copper phthalocyanine 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 is excellent in viscosity suitability and excellent in re-solubility in the glycol ether-based ink which has recently been required.
  • viscosity suitability refers to the initial viscosity and the viscosity over time when the ink is prepared.
  • resolubility refers to the solubility of the pigment composition in the ink once it has become a dry substance in the solvent constituting the ink. For example, low resolubility (poor) means that the pigment composition is once again difficult to dissolve in a solvent once it becomes a dry product.
  • the copper phthalocyanine pigment used in the present invention is a copper phthalocyanine crude ( ⁇ ) which is finely pulverized by dry grinding and then converted to a ⁇ type by solvent pigmentation, or copper phthalocyanine crude ( ⁇ ) is an inorganic salt together with a solvent
  • examples include ⁇ -type copper phthalocyanine obtained by heat-grinding treatment using crystals.
  • a commercially available product for example, FASTOGEN BLUE 5362K or FASTOGEN BLUE TGR manufactured by DIC, etc. may be used
  • an ⁇ -type copper phthalocyanine pigment or other structural pigment may be contained within a range not to adversely affect the performance as needed, such as hue adjustment.
  • well-known processes may be added appropriately after production to be used in the present invention.
  • 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
  • the “C 1 to C 20 alkyl group” which is a 6 to C 20 alkyl group means a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n- group Heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n- Heptadecyl group, n-
  • the “C 6 -C 20 alkyl group” that can be taken by at least one of R 1 , R 2 , R 3 and R 4 is n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, An n-icosyl group and the like can be mentioned, but from the viewpoint of resolubility, a C 8 to C 18 alkyl group is preferable, and a C 10 to C 15 alkyl group is more preferable.
  • R 1 , R 2 , R 3 and R 4 be “C 6 to C 20 alkyl groups”, Examples of the C 6 -C 20 alkyl group "include those described above.
  • R 1 , R 2 , R 3 and R 4 are “C 6 to C 20 alkyl group”, the remaining one to three are a hydrogen atom or C 1 to C 20 It is known that too many long-chain alkyl groups cause resistance in the ink and cause thickening of the ink.
  • a C 1 to C 3 alkyl group is preferable because the adsorption inhibition of the dispersion resin and the decrease in the compatibility with the ink solvent may be caused by the steric hindrance of the long chain alkyl group.
  • all of R 1 , R 2 , R 3 and R 4 may be “C 6 -C 20 alkyl group”.
  • the copper phthalocyanine skeleton acts as an adsorption site to the copper phthalocyanine pigment, and the sulfonic acid quaternary ammonium salt moiety acts as a compatible group with the glycol ether solvent.
  • the dispersibility of the pigment and the pigment derivative represented by the formula (I) in the ink solvent is improved, and good resolubility can be expressed by appropriately inhibiting the film formation of the resin.
  • the resin when the sulfo group acts as an adsorption site for NC resin or the like, the resin can be adsorbed on the surface of the pigment and the pigment derivative represented by the formula (I). Therefore, the resin resistance in the ink solvent is reduced, and the effect of lowering the ink viscosity is obtained.
  • the present invention is based on the finding that the effect of the present invention can be obtained by using a pigment derivative having a specific structure with respect to copper phthalocyanine among trial derivatives by countless possible derivatives. Since the present invention is found by trial and error, the mechanism of action is not clear, but the present inventors examined from the following viewpoints. If the pigment or the pigment derivative does not quickly conform to the ink solvent, only the ink resin preferentially bonds and forms a film preferentially in the drying process, and the resolubility in the ink solvent is significantly reduced.
  • the pigment or the pigment derivative is uniformly dispersed between the coating films to obtain an appropriate coating film strength in which resolubility is expressed. It is believed that things will be possible. This effect can not be exhibited by the addition of derivatives such as those conventionally studied, such as monosubstituted copper phthalocyanine sulfonic acid primary ammonium salts.
  • 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 is an alkyl group ⁇ C 20, groups represented by the formula (II) in the two (SO 3 NR 5 R 6 R 7 R 8) may or may not be the same or different, are identical It is desirable from an industrial point of view.
  • the “C 1 to C 20 alkyl group” means methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-group -Nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-octadecyl group And -nonadecyl group, n-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 take is n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n -Decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-nonadecyl group -Icosyl group and the like can be mentioned, but from the viewpoint of resolubility, a C 8 to C 18 alkyl group is preferable, and a C 10 to C 15 alkyl group is more preferable.
  • R 5 , R 6 , R 7 and R 8 be “C 6 to C 20 alkyl groups”, Examples of the C 6 -C 20 alkyl group "include those described above.
  • R 5 , R 6 , R 7 and R 8 are “C 6 to C 20 alkyl group”
  • the remaining one to three are a hydrogen atom or C 1 to C 20 It is known that too many long-chain alkyl groups cause resistance in the ink and cause thickening of the ink.
  • a C 1 to C 3 alkyl group is preferable because the adsorption inhibition of the dispersion resin and the decrease in the compatibility with the ink solvent may be caused by the steric hindrance of the long chain alkyl group.
  • all of R 5 , R 6 , R 7 and R 8 may be “C 6 -C 20 alkyl group”.
  • the pigment composition of the present invention can further obtain the effects of the present invention by further having a derivative of the formula (II).
  • a copper phthalocyanine skeleton functions as an adsorption site to a copper phthalocyanine pigment
  • a sulfonic acid quaternary ammonium salt portion functions as a compatible group with a glycol ether solvent. Therefore, the dispersibility of the pigment and the pigment derivative represented by the formula (I) in the ink solvent is improved, and good resolubility can be expressed by appropriately inhibiting the film formation of the resin. Moreover, since it is a disubstituted compound, the resolubility improvement effect is high compared with Formula (I).
  • the pigment composition of the present invention can further obtain the effects of the present invention by further having a derivative of the formula (III).
  • the derivative has a copper phthalocyanine skeleton acting as an adsorption site to a copper phthalocyanine pigment while a sulfo group acts as an adsorption site such as NC resin.
  • the resin can be adsorbed on the surface of the pigment and the pigment derivative represented by the formula (III). Therefore, the resin resistance in the ink solvent is reduced, and the effect of lowering the ink viscosity is obtained.
  • the pigment derivative represented by the formula (I) is 0.1 to 10.0 parts by mass with respect to 100 parts by mass of the ⁇ -type copper phthalocyanine pigment, and the pigment derivative represented by the formula (II) is 0.1
  • the total amount of the pigment derivative represented by the formula (I) and the pigment derivative represented by the formula (II) is 10.0 parts by mass or less.
  • each pigment derivative is shown. Either method may be adopted.
  • di-substituted copper phthalocyanine pigment sulfonic acid derivative as a raw material, di-substituted copper phthalocyanine pigment sulfonic acid derivatives produced by a commercially available method or a commonly used method can be used, and as a commonly used method, for example, copper phthalocyanine Disubstituted copper phthalocyanine pigment sulfonic acid derivatives can be prepared by sulfonation of the pigment with concentrated sulfuric acid or oleum, or by sulfochlorination of the above starting material 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 disubstituted copper phthalocyanine pigment sulfonic acid derivative.
  • Formula (I) can be obtained by using 0.5 mol of amine per mol of sulfo group of disubstituted copper phthalocyanine pigment sulfonic acid derivative, per mol of sulfo group of disubstituted copper phthalocyanine pigment sulfonic acid derivative By using 1 mole of amine, it is possible to produce a pigment derivative of the formula (III) by acid-precipitating the disubstituted copper phthalocyanine pigment sulfonic acid derivative and filtering off the disubstituted copper phthalocyanine pigment.
  • the copper phthalocyanine crude is dry ground with an attritor to obtain a copper phthalocyanine ground product.
  • Water, xylene, rosin and disubstituted copper phthalocyanine sulfonic acid are added to the copper phthalocyanine attrition to carry out pigmenting at 93 ° C. for 3 hours.
  • After completion of the pigmentation add disubstituted copper phthalocyanine sulfonic acid and additionally disperse at 93 ° C. for 1 hour.
  • the pigment composition of the present invention can be obtained by powder-blending a disubstituted copper phthalocyanine sulfonic acid quaternary ammonium salt with the obtained powder pigment composition.
  • a similar pigment composition can also be obtained by introducing the formulas (I), (II) and (III) into the kneader grinding pigmentation.
  • the same pigment composition can also be obtained by mixing the dried derivatives of Formula (I), Formula (II), and Formula (III) with the dried copper phthalocyanine pigment. It is also possible to combine two or more of the above manufacturing methods.
  • 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 (beta) -type copper phthalocyanine 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 and 3-heptanone, ethyl acetate, n-propyl acetate, isopropyl acetate, isobutyl acetate
  • Ester solvents such as methanol, ethanol, n-propanol, isopropanol, alcohol solvents such as n-butanol, isobutanol, t-butanol, propylene glycol monoethyl ether (herein, 1-ethoxy-2-propanol and the like) May be written), propylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, (Poly) alkylene glycol monoalkyl
  • glycol ether solvents refer to (poly) alkylene glycol monoalkyl ether solvents and (poly) alkylene glycol monoalkyl ether acetate solvents among the above solvents.
  • glycol solvents include ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, propylene glycol monomethyl ether, Propyl cellosolve and dipropylene glycol monomethyl ether are 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 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 Dry grinding was performed on copper phthalocyanine crude manufactured by DIC Corporation using an attritor to obtain a copper phthalocyanine ground material.
  • a copper phthalocyanine ground product 330 parts of a rosin solution and 450 parts of (1) copper phthalocyanine sulfonic acid solution were added.
  • 15 parts of xylene was added, and the mixture was stirred at 93 ° C. for 3 hours.
  • (2) 330 parts of a copper phthalocyanine sulfonic acid solution was added and additionally dispersed at 93 ° C. for 1 hour.
  • C dimethyldialkyl
  • Example 1 The following items used in Example 1 will be described below. Rosin solution 4.6 parts of a 20% aqueous sodium hydroxide solution and 4.4 parts of hydrogenated rosin were added to 321 parts of water, and the hydrogenated rosin was dissolved by heating and stirring. -About the above (1) copper phthalocyanine sulfonic acid solution, 7.4 parts of 20% aqueous sodium hydroxide solution and 8.2 parts of copper phthalocyanine sulfonic acid (number of substituents 2) are added to 434.4 parts of water, and the copper phthalocyanine is heated and stirred. A solution of sulfonic acid.
  • Example 2 Dry grinding was performed on copper phthalocyanine crude manufactured by DIC Corporation using an attritor to obtain a copper phthalocyanine ground material. To 200 parts of this copper phthalocyanine ground product, 330 parts of a rosin solution and 450 parts of (1) copper phthalocyanine sulfonic acid solution were added. To this was added 220 parts of water and heated to 93 ° C. Immediately after completion of the heating, 15 parts of xylene is added and the mixture is stirred at 93 ° C. for 3 hours. Thereafter, the temperature was raised to 100 ° C. to distill off xylene.
  • Example 2 The following items used in Example 2 will be described below.
  • a rosin solution 4.6 parts of a 20% aqueous sodium hydroxide solution and 4.4 parts of hydrogenated rosin were added to 321 parts of water, and the hydrogenated rosin was dissolved by heating and stirring.
  • copper phthalocyanine sulfonic acid solution add 7.4 parts of a 20% aqueous sodium hydroxide solution and 5.0 parts of copper phthalocyanine sulfonic acid (number of substituents 2) to 432 parts of water, and heat stir to give copper phthalocyanine sulfonic acid Dissolved.
  • the pH was adjusted to 6.8 to 7.5, and filtration was performed to obtain a presscake of copper phthalocyanine sulfonic acid quaternary ammonium salt. This is dried and pulverized to obtain a powdered copper phthalocyanine sulfonic acid quaternary ammonium salt.
  • Example 3 Copper phthalocyanine crude manufactured by DIC Co. was dry-ground with an attritor to obtain a copper phthalocyanine-ground product.
  • (Second step) To 200 parts of this copper phthalocyanine ground product, 330 parts of a rosin solution and (1) 450 parts of a copper phthalocyanine sulfonic acid solution were added. To this was added 220 parts of water and heated to 93 ° C. Immediately after completion of heating, 15 parts of xylene was added, and the mixture was stirred at 93 ° C. for 3 hours. After the completion of the stirring, (2) 330 parts of a copper phthalocyanine sulfonic acid solution was added and additionally dispersed at 93 ° C.
  • Example 3 The following items used in Example 3 will be described below. Rosin solution 15 parts of a 20% aqueous sodium hydroxide solution and 15.0 parts of hydrogenated rosin are added to 321 parts of water, and the hydrogenated rosin is dissolved by heating and stirring. -About the above (1) copper phthalocyanine sulfonic acid solution, 7.4 parts of 20% aqueous sodium hydroxide solution and 8.3 parts of copper phthalocyanine sulfonic acid (number of substituents 2) are added to 434.4 parts of water, and the copper phthalocyanine is heated and stirred. A solution of sulfonic acid.
  • Example 4 Dry grinding was performed on copper phthalocyanine crude manufactured by DIC Corporation using an attritor to obtain a copper phthalocyanine ground material.
  • a copper phthalocyanine ground product 330 parts of a rosin solution and 450 parts of (1) copper phthalocyanine sulfonic acid solution were added.
  • 15 parts of xylene was added, and the mixture was stirred at 93 ° C. for 3 hours.
  • (2) 330 parts of a copper phthalocyanine sulfonic acid solution was added and additionally dispersed at 93 ° C. for 1 hour.
  • C dimethyldialkyl
  • Example 4 The following items used in Example 4 will be described below.
  • a rosin solution 4.6 parts of a 20% aqueous sodium hydroxide solution and 4.4 parts of hydrogenated rosin were added to 321 parts of water, and the hydrogenated rosin was dissolved by heating and stirring.
  • copper phthalocyanine sulfonic acid solution 7.4 parts of 20% aqueous sodium hydroxide solution and 8.2 parts of copper phthalocyanine sulfonic acid (number of substituents 2) are added to 434.4 parts of water, and the copper phthalocyanine is heated and stirred.
  • a solution of sulfonic acid 7.4 parts of 20% aqueous sodium hydroxide solution and 8.2 parts of copper phthalocyanine sulfonic acid (number of substituents 2) are added to 434.4 parts of water, and the copper phthalocyanine is heated and stirred.
  • a solution of sulfonic acid 7.4 parts of 20% aqueous sodium hydroxide solution and 8.2 parts of copper
  • the solution of the above (2) copper phthalocyanine sulfonic acid is added to 323.1 parts of water, 4.3 parts of a 20% aqueous sodium hydroxide solution and 2.6 parts of copper phthalocyanine sulfonic acid (number of substituents) are added, and the copper phthalocyanine is heated and stirred.
  • Comparative example 2 Dry grinding was performed on copper phthalocyanine crude manufactured by DIC Corporation using an attritor to obtain a copper phthalocyanine ground material. 3960 parts of isobutanol and 8040 parts of water were added to 1350 parts of the copper phthalocyanine attrition. After heating to 89 ° C. and reflux pigmenting for 1 hour, isobutanol was distilled off. Water was then added until the total amount was 12000 parts. It was dried by a spray dryer to obtain a powder pigment. To 200.0 parts of this copper phthalocyanine powder pigment, 14.0 parts of copper phthalocyanine sulfonic acid (number of substituents: 2) was powder blended. Thus, a powdery pigment composition was obtained.
  • Evaluation Ink Preparation of Evaluation Ink 17.3 parts of pigment, 8.9 parts of NC resin, 48.7 parts of propylene glycol monoethyl ether (manufactured by Kanto Chemical Co., Ltd.), n-propyl alcohol (Kanto Chemical Co., Ltd.) 8.0 parts, ethanol (Kanto Chemical Co., Ltd.) 11.0 parts, ethyl acetate (Kanto Chemical Co., Ltd.) 6.1 parts, SAZ beads (Tokyo Glass Instruments Co., Ltd.
  • zirconia YTZ ball 1.25 ⁇
  • One hundred and fifty (150) parts were placed in a 200 mL glass bottle and dispersed for 2 hours with Shaker Skandex SK550 (manufactured by Fast & Fluid Management B. V. Company) to obtain an evaluation ink.
  • Shaker Skandex SK550 manufactured by Fast & Fluid Management B. V. Company
  • Viscosity evaluation method The viscosity was measured at 6 to 120 RPM using a Brookfield viscometer (model: DV3TRVTJO).
  • Re-dissolving test method The ink prepared in (2) was spread on a re-dissolving evaluation plate. After that, it was dried with a dryer for 1 minute. Thereafter, ethanol (manufactured by Kanto Chemical Co., Ltd.) was poured on the ink-coated surface dried from the top of the resolubility evaluation plate. If the dried ink coating surface fell, it was judged that the resolubility was good, and if it did not fall, it was defective. When it was not possible to make a judgment alone, it was displayed side-by-side with the target ink coating surface, and the superiority was judged by comparison.
  • Example 1 contains Formula (I) and Formula (II), and low viscosity-ization can be achieved because Formula (I) works as a resin adsorption site. Moreover, Formula (I) and Formula (II) are highly compatible with the glycol ether solvent, and good resolubility is expressed. The resolubility improving effect is higher in the formula (II) than in the formula (I).
  • Example 2 contains Formula (I), Formula (II), and Formula (III), and a low viscosity-ization can be achieved because Formula (I) and Formula (III) work as a resin adsorption site.
  • the formula (I) and the formula (II) are highly compatible with the glycol ether solvent, and good resolubility is expressed.
  • Formula (III) shows a better resin adsorption effect than Formula (I). The resolubility improving effect is higher in the formula (II) than in the formula (I).
  • Example 3 contains Formula (I) and Formula (III), and low viscosity-ization can be achieved by each acting as a resin adsorption site. Further, the formula (I) is highly compatible with the glycol ether solvent, and resolubility is developed. Formula (III) shows a better resin adsorption effect than Formula (I).
  • Example 4 contains only Formula (I), coexistence of low viscosity-ization and resolubility improvement effect can be achieved. However, since the formula (II) and the formula (III) are not contained, the effect is low.
  • Comparative Example 1 contains only the formula (II), the compatibility with the glycol ether solvent is high, and good resolubility is exhibited. However, the viscosity is extremely high because it does not contain the formula (I) or the formula (III), which is not a range that can be used industrially.
  • Comparative Example 2 contains only the formula (III), it works as a resin adsorption site and can achieve viscosity reduction. However, it does not contain formula (I) and formula (II), it is significantly inferior to resolubility and can not be used industrially.

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Abstract

Le problème abordé par la présente invention est de pourvoir à une composition de pigment phtalocyanine de cuivre qui fait preuve d'une excellente aptitude à la redissolution et une bonne viscosité (viscosité initiale, viscosité dans le temps) avec des encres à base d'éther de glycol. La solution selon l'invention porte sur une composition de pigment phtalocyanine de cuivre caractérisée en ce qu'elle comprend un pigment phtalocyanine de cuivre sous forme β et un dérivé de pigment représenté par la formule (I) [dans la formule, R1, R2, R3, et R4 représentent chacun indépendamment un atome d'hydrogène ou un groupe alkyle en C1 à C20, et au moins l'un des R1, R2, R3, et R4 est un groupe alkyle en C6 à C20].
PCT/JP2018/044512 2017-12-22 2018-12-04 Composition de pigment phtalocyanine de cuivre et composition d'encre la contenant WO2019124050A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7419822B2 (ja) 2020-01-08 2024-01-23 Dic株式会社 極細繊維着色用マスターバッチ、及び極細繊維

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5233922A (en) * 1975-09-09 1977-03-15 Ciba Geigy Ag Pigment compositions containing phthalocyanine pigments
JPH01144476A (ja) * 1987-12-01 1989-06-06 Toyo Ink Mfg Co Ltd カラーチップの製造法
JPH01144475A (ja) * 1987-12-01 1989-06-06 Toyo Ink Mfg Co Ltd カラーチップの製造法
JPH01203472A (ja) * 1988-02-10 1989-08-16 Dainippon Ink & Chem Inc 顔料組成物
JPH09506922A (ja) * 1993-12-23 1997-07-08 ゼネカ・リミテッド 方 法
JP2004175975A (ja) * 2002-11-28 2004-06-24 Dainippon Ink & Chem Inc 表面処理有機顔料の製造方法及び印刷インキ
JP2010533744A (ja) * 2007-07-17 2010-10-28 クラリアント・ファイナンス・（ビーブイアイ）・リミテッド Ｃ．ｉ．ピグメントブルー１５：６をベースとする顔料調合物
WO2015015832A1 (fr) * 2013-07-31 2015-02-05 Dic株式会社 Composition de pigment phtalocyanine, procédé pour la fabriquer et encre

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5233922A (en) * 1975-09-09 1977-03-15 Ciba Geigy Ag Pigment compositions containing phthalocyanine pigments
JPH01144476A (ja) * 1987-12-01 1989-06-06 Toyo Ink Mfg Co Ltd カラーチップの製造法
JPH01144475A (ja) * 1987-12-01 1989-06-06 Toyo Ink Mfg Co Ltd カラーチップの製造法
JPH01203472A (ja) * 1988-02-10 1989-08-16 Dainippon Ink & Chem Inc 顔料組成物
JPH09506922A (ja) * 1993-12-23 1997-07-08 ゼネカ・リミテッド 方 法
JP2004175975A (ja) * 2002-11-28 2004-06-24 Dainippon Ink & Chem Inc 表面処理有機顔料の製造方法及び印刷インキ
JP2010533744A (ja) * 2007-07-17 2010-10-28 クラリアント・ファイナンス・（ビーブイアイ）・リミテッド Ｃ．ｉ．ピグメントブルー１５：６をベースとする顔料調合物
WO2015015832A1 (fr) * 2013-07-31 2015-02-05 Dic株式会社 Composition de pigment phtalocyanine, procédé pour la fabriquer et encre

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7419822B2 (ja) 2020-01-08 2024-01-23 Dic株式会社 極細繊維着色用マスターバッチ、及び極細繊維

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