WO2022176337A1 - アゾ顔料、インキ、塗料、プラスチック用着色剤、着色成形品、文具・筆記具用着色剤、捺染剤、トナー、カラーフィルタ用分散液・レジスト、及び化粧料 - Google Patents
アゾ顔料、インキ、塗料、プラスチック用着色剤、着色成形品、文具・筆記具用着色剤、捺染剤、トナー、カラーフィルタ用分散液・レジスト、及び化粧料 Download PDFInfo
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- WO2022176337A1 WO2022176337A1 PCT/JP2021/045264 JP2021045264W WO2022176337A1 WO 2022176337 A1 WO2022176337 A1 WO 2022176337A1 JP 2021045264 W JP2021045264 W JP 2021045264W WO 2022176337 A1 WO2022176337 A1 WO 2022176337A1
- Authority
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- WIPO (PCT)
- Prior art keywords
- pigment
- parts
- azo pigment
- water
- azo
- Prior art date
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- 239000000049 pigment Substances 0.000 title claims abstract description 489
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- 238000007639 printing Methods 0.000 title claims description 41
- 239000003086 colorant Substances 0.000 title claims description 27
- 239000006185 dispersion Substances 0.000 title claims description 19
- 239000003973 paint Substances 0.000 title claims description 17
- 239000003795 chemical substances by application Substances 0.000 title claims description 12
- 239000002537 cosmetic Substances 0.000 title claims description 12
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- 239000004033 plastic Substances 0.000 title claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 133
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- 229910052751 metal Inorganic materials 0.000 claims abstract description 42
- 239000002184 metal Substances 0.000 claims abstract description 39
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 claims abstract description 28
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 26
- 239000004753 textile Substances 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 abstract description 11
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 156
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- 238000003756 stirring Methods 0.000 description 57
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- 230000000052 comparative effect Effects 0.000 description 48
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- 238000005259 measurement Methods 0.000 description 33
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- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000005385 peroxodisulfate group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229940104573 pigment red 5 Drugs 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012066 reaction slurry Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000007613 slurry method Methods 0.000 description 1
- STZCRXQWRGQSJD-UHFFFAOYSA-N sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonic acid Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0014—Monoazo dyes prepared by diazotising and coupling from diazotized aminonaphthalene
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/103—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the naphthalene series
- C09B29/106—Hydroxy carboxylic acids of the naphthalene series
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
- C09B35/03—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
- C09B35/035—Disazo dyes characterised by two coupling components of the same type in which the coupling component containing an activated methylene group
-
- 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
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0007—Coated particulate pigments or dyes with inorganic coatings
-
- 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
Definitions
- the present invention relates to azo pigments and inks, paints, coloring agents for plastics, colored molded articles, coloring agents for stationery and writing instruments, textile printing agents, toners, dispersions and resists for color filters, and cosmetics containing the azo pigments.
- Azo pigments have long been used mainly for coloring inks, paints, toners, rubber and plastics, undiluted coloring for synthetic fibers, pigment printing, and coloring miscellaneous goods. Among them, printing applications such as ink are important. Printing is performed by making a printing plate, applying printing ink to the surface of the plate, and transferring it to paper, film, cloth, or the like. Printing plates include planographic, intaglio, letterpress, and stencil, and there are printing methods such as offset printing, gravure printing, and flexographic printing depending on the shape of the plate. In gravure printing using an intaglio, in the case of multicolor printing, printing is normally performed in the order of black, cyan, magenta, and yellow.
- ink-jet printing in which ink is directly sprayed onto paper.
- another color is printed on top of the previously printed color, so the ink is required to be transparent in order to obtain a printed matter with a clear image.
- the transparency of ink depends on the performance of pigments, which are colorants.
- a method of refining a condensed disazo pigment by solvent salt milling is known.
- zeta potential is used in various fields as a parameter for evaluating the degree of dispersion stability and aggregation of colloidal particles such as pigments.
- a method of obtaining transparency of an inkjet ink image is known by setting the zeta potential to a specific value.
- the disazo pigment is kneaded with a water-soluble inorganic salt and a water-soluble solvent to make it finer, thereby suppressing light scattering and increasing the transparency of the coating film.
- a water-soluble inorganic salt and a water-soluble solvent to make it finer, thereby suppressing light scattering and increasing the transparency of the coating film.
- the zeta potential is measured by diluting the pigment after making it into an inkjet ink.
- the zeta potential is given by the type and amount of surfactant used when dispersing the pigment, and the addition of an additive having an electric charge. It is difficult to adjust to the desired zeta potential.
- a dispersion network is formed by pigment-resin-solvent-additive, so the resin and additive are present around the pigment. Therefore, even if it is measured by this method, the zeta potential of the pigment wrapped in the resin or additive is only measured, and it cannot be said that the zeta potential of the pigment particles is purely measured. In other words, it cannot be said that the zeta potential in Patent Document 2 represents the aggregation or dispersion state of the pigment, and as a result, it cannot be said that an ink with excellent transparency and low viscosity is obtained.
- an object of the present invention is to provide an azo pigment, an ink, etc., which are excellent in transparency, good in dispersibility, and low in viscosity.
- IPA isopropanol
- the azo group has a strong color-developing effect, and the auxochromic group can adjust the hue over a wide range from yellow, orange, red, purple, blue, and brown. Due to these advantages, more than half of the organic pigments registered in the Color Index are azo pigments. Therefore, it is very important to improve the transparency and dispersibility of azo pigments.
- the present inventors focused on the zeta potential of an azo pigment in an IPA solvent, and as a result of further studies, by controlling the zeta potential to a specific range, excellent transparency and dispersion The present inventors have found that an azo pigment having good properties and low viscosity can be obtained, and have completed the present invention.
- Patent Document 2 the magenta pigment ink is diluted 1000 times and the zeta potential is measured. Although there is no clear description of the medium for dilution, since the magenta pigment dispersion was diluted with pure water when the magenta pigment ink was produced, it is believed that pure water is used even at the zeta potential. Therefore, in Patent Document 2, water is used as a solvent for zeta potential measurement, and the zeta potential in IPA cannot be easily conceived from Patent Document 2.
- Pigment particles are nano-level particles (primary particles), and the primary particles aggregate due to van der Waals forces between particles to form secondary particles.
- the secondary particles of the pigment are crushed into primary particles in the dispersion process, but if no measures are taken, the primary particles will reaggregate due to the attractive force between the particles. Since aggregates are coarse, they have a strong effect of scattering light, which causes deterioration of transparency. Furthermore, the formation of agglomerates impairs the mobility of the pigment particles and increases the viscosity due to the immobilization of solvent molecules in the interstices of the particles.
- a pigment with a specific zeta potential in IPA is used.
- the repulsion of the electric double layer of the pigment particles suppresses the particles from approaching each other and prevents aggregation, thereby obtaining good dispersibility and transparency.
- the simplest method is to treat an ionic substance such as a metal salt, but if the metal salt and the pigment are simply mixed, the salt easily flows out from the pigment particles. Therefore, in the coexistence of the pigment and the metal salt, the metal is oxidized with an oxidizing agent to treat the surface of the pigment particles with the metal.
- metals and oxidizing agents there are many choices of metals and oxidizing agents, and it is economically advantageous to select inexpensive compounds. Since the reaction between a metal and an oxidizing agent is complicated, it is difficult to specify what kind of compound the metal is, but if the metal is iron, for example, it becomes iron oxide or iron oxyhydroxide. We estimate that The presence of the metal on the pigment surface thus gives a certain zeta potential in IPA. In the present invention, it is important that the metal be present on the surface of the pigment particles. It is not sufficient that the metal element is contained in the structure of the pigment. Dispersibility is not obtained.
- the present invention "Section 1. An azo pigment having a zeta potential of -80 mV to -30 mV in isopropanol (IPA). Section 2. Item 1. The azo pigment according to Item 1, which contains 0.05 to 2.00 parts by mass of the metal element per 100 parts by mass of the azo pigment. Item 3. Item 3. The azo pigment according to item 2, wherein the metal element is an iron element. Section 4. Item 3, wherein the ratio (Fe/C) of the azo pigment particle surface iron element concentration Fe (atomic%) and the azo pigment particle surface carbon element concentration C (atomic%) measured by X-ray photoelectron spectroscopy is 0.20 or less. azo pigments. Item 5.
- Item 6. A paint containing the azo pigment according to any one of Items 1 to 4, a coloring agent for plastics, a colored molded product, a coloring agent for stationery and writing instruments, a textile printing agent, a toner, a dispersion/resist for a color filter, and a cosmetic. fee. ] Regarding.
- the azo pigment of the present invention has excellent transparency, good dispersibility, and low viscosity. Therefore, the azo pigment of the present invention is suitable for ink (particularly printing ink and inkjet ink). In addition to ink applications, the azo pigment of the present invention can also be used for various applications such as paints, coloring agents for plastics, coloring agents for stationery and writing instruments, textile printing agents, toners, dispersions and resists for color filters, and cosmetics. can be done.
- the azo pigment of the present invention has a zeta potential of -80 mV to -30 mV in isopropanol (IPA).
- the zeta potential is preferably -70 mV to -35 mV, more preferably -60 mV to -40 mV.
- IPA isopropanol
- the azo pigment of the present invention has a zeta potential in water of, for example, -50 mV to 50 mV, preferably -25 mV to 25 mV, more preferably -10 mV to 10 mV.
- the zeta potential can be measured with a zeta potential/particle size/molecular weight measurement system by electrophoretic light scattering measurement.
- the azo pigment of the present invention preferably contains a metallic element (metal).
- the metal element (metal) is not limited to a metal simple substance, and may be in the form of a metal compound such as an oxide or a hydroxide.
- the metal element (metal) is presumed to exist on the surface of the azo pigment particles. This metallic element (metal) cannot be removed from the pigment simply by washing with water or the like. Therefore, the metal element (metal) interacts with the primary particles of the pigment, affecting the physical properties of the azo pigment, and further affecting the physical properties when the azo pigment is used as an ink.
- the content of the metal element is, for example, 0.05 to 2.00 parts by mass, preferably 0.10 to 1.80 parts by mass, more preferably 0.30 to 1.50 parts by mass per 100 parts by mass of the azo pigment. be.
- the content of a metal element is converted as a single metal element even if it is in the form of a metal compound such as an oxide or hydroxide.
- the zeta potential is easily set within the above range.
- the content of the metal element can be measured, for example, by subjecting the pigment to fluorescent X-ray spectroscopy or ICP emission spectroscopy/mass spectrometry.
- the metal elements include iron, copper, silver, nickel, zinc, chromium, titanium, cobalt, vanadium, manganese, gallium, zirconium, niobium, molybdenum, technetium, ruthenium, rhodium, palladium, cadmium, indium, A tin element is mentioned.
- an iron element (iron) is preferable as the metal element (metal).
- the iron element may contain Fe as an element, and may be in the form of an iron compound such as iron oxide or iron hydroxide. Therefore, the azo pigment of the present invention preferably contains the iron element within the above range.
- the ratio of the azo pigment particle surface iron element concentration Fe (atomic%) by X-ray photoelectron spectroscopy to the azo pigment particle surface carbon element concentration C (atomic%) ( Fe/C) is preferably 0.20 or less (eg, 0.0001 to 0.20). In addition, the Fe/C is more preferably 0.15 or less, still more preferably 0.10 or less. When the Fe/C is within the above range, the zeta potential is easily set within the above range. The Fe/C can be measured, for example, with an X-ray photoelectron spectrometer.
- azo pigments include C.I. I. Pigment Red 10, C.I. I. Pigment Red 11, C.I. I. Pigment Red 112, C.I. I. Pigment Red 114, C.I. I. Pigment Red 119, C.I. I. Pigment Red 12, C.I. I. Pigment Red 136, C.I. I. Pigment Red 14, C.I. I. Pigment Red 144, C.I. I. Pigment Red 146, C.I. I. Pigment Red 147, C.I. I.
- Pigment Red 15 C.I. I. Pigment Red 150, C.I. I. Pigment Red 16, C.I. I. Pigment Red 164, C.I. I. Pigment Red 166, C.I. I. Pigment Red 17, C.I. I. Pigment Red 170, C.I. I. Pigment Red 171, C.I. I. Pigment Red 175, C.I. I. Pigment Red 176, C.I. I. Pigment Red 18, C.I. I. Pigment Red 183, C.I. I. Pigment Red 184, C.I. I. Pigment Red 185, C.I. I. Pigment Red 187, C.I. I. Pigment Red 188, C.I. I. Pigment Red 193, C.I. I.
- Pigment Red 2 C.I. I. Pigment Red 200, C.I. I. Pigment Red 208, C.I. I. Pigment Red 21, C.I. I. Pigment Red 210, C.I. I. Pigment Red 211, C.I. I. Pigment Red 213, C.I. I. Pigment Red 214, C.I. I. Pigment Red 22, C.I. I. Pigment Red 220, C.I. I. Pigment Red 221, C.I. I. Pigment Red 23, C.I. I. Pigment Red 237, C.I. I. Pigment Red 238, C.I. I. Pigment Red 239, C.I. I. Pigment Red 242, C.I. I. Pigment Red 243, C.I. I. I.
- Pigment Yellow 154 C.I. I. Pigment Yellow 155, C.I. I. Pigment Yellow 16, C.I. I. Pigment Yellow 165, C.I. I. Pigment Yellow 166, C.I. I. Pigment Yellow 167, C.I. I. Pigment Yellow 168, C.I. I. Pigment Yellow 169, C.I. I. Pigment Yellow 17, C.I. I. Pigment Yellow 170, C.I. I. Pigment Yellow 172, C.I. I. Pigment Yellow 174, C.I. I. Pigment Yellow 175, C.I. I. Pigment Yellow 176, C.I. I. Pigment Yellow 180, C.I. I. Pigment Yellow 181, C.I. I.
- Pigment Yellow 183 C.I. I. Pigment Yellow 191, C.I. I. Pigment Yellow 191:1, C.I. I. Pigment Yellow 194, C.I. I. Pigment Yellow 2, C.I. I. Pigment Yellow 205, C.I. I. Pigment Yellow 206, C.I. I. Pigment Yellow 209, C.I. I. Pigment Yellow 212, C.I. I. Pigment Yellow 214, C.I. I. Pigment Yellow 219, C.I. I. Pigment Yellow 3, C.I. I. Pigment Yellow 4, C.I. I. Pigment Yellow 49, C.I. I. Pigment Yellow 5, C.I. I. Pigment Yellow 55, C.I. I. Pigment Yellow 6, C.I. I.
- Pigment Orange 46 C.I. I. Pigment Orange 5, C.I. I. Pigment Orange 60, C.I. I. Pigment Orange 62, C.I. I. Pigment Orange 64, C.I. I. Pigment Orange 72, C.I. I. Pigment Orange 74, C.I. I. Pigment Brown 25, C.I. I. Pigment Brown 32, C.I. I. Pigment Brown 5, C.I. I. Pigment Blue 25, C.I. I. Pigment Blue 26, C.I. I. Pigment Violet 13, C.I. I. Pigment Violet 17, C.I. I. Pigment Violet 32, C.I. I. Pigment Violet 50 may be mentioned, and may be used alone or in combination.
- C.I. I. Pigment Red 57:1 PR57:1
- C.I. I. Pigment Red 146 PR146
- C.I. I. Pigment Yellow 13 PY13
- C.I. I. Pigment Yellow 55 PY55
- C.I. I. Pigment Yellow 83 PY83
- C.I. I. Pigment Yellow 180 PY180
- C.I. I. Pigment Range 13 PO13
- the primary particle size of the azo pigment is, for example, 0.01 to 1.0 ⁇ m, preferably 0.1 to 0.6 ⁇ m.
- the specific surface area of the azo pigment is, for example, 10 to 150 m 2 /g, preferably 20 to 100 m 2 /g. When the primary particle size and specific surface area are within the above ranges, the pigment can have excellent coloring power and dispersibility.
- the azo pigment of the present invention may contain pigment derivatives such as sulfonic acid pigment derivatives, amino group-containing pigment derivatives, and phthalimidomethyl group-containing pigment derivatives, polymers such as dispersants, surfactants, rosin, and the like.
- the azo pigment of the present invention may contain an inorganic pigment. Examples of inorganic pigments include calcium carbonate, magnesium carbonate, precipitated barium sulfate, kaolin, clay, alumina white, and white carbon.
- the azo pigment of the present invention can be obtained, for example, through 1) synthesis of an azo pigment, and 2) pigment surface treatment after synthesis.
- First, 1) an azo pigment can be synthesized by coupling a diazo component comprising an aromatic amine diazonium salt with a coupler component comprising an aromatic compound other than the aromatic amine constituting the diazonium salt.
- An aromatic amine diazonium salt which is a diazo component, can be obtained by acidifying an aromatic amine with hydrochloric acid and adding an aqueous sodium nitrite solution. Coupling of the diazo component and the coupler component is carried out under alkaline conditions using sodium hydroxide or the like.
- the azo compound obtained after coupling is a soluble azo (dye)
- it may be made insoluble by adding an aqueous solution of a metal salt such as calcium or barium to obtain a metal-laked azo pigment.
- a metal salt such as calcium or barium
- a commercially available azo pigment may be used as it is instead of being synthesized by a coupling reaction as described above.
- the pigment slurry may be prepared by: 1) separating the azo pigment obtained in the synthesis of the azo pigment by filtration and stirring this in a solvent; alternatively, the reaction slurry after the coupling reaction may be used as the pigment slurry as it is. good too.
- Water and/or an organic solvent can be used as the solvent, and the organic solvent can be methanol, ethanol, n-propanol, i-propanol, or the like.
- the water is particularly preferred from the point of view of economy.
- the water may be pure water or industrial water, and furthermore, acetate buffer, phosphate buffer, citrate buffer, citrate phosphate buffer, borate buffer, tartrate buffer. You may use buffers, such as.
- the amount of the azo pigment added is preferably 1 to 30 parts by mass with respect to 100 parts by mass of the solvent. When the amount added is small, the productivity is low. Therefore, 2 to 20 parts by mass is more preferable.
- the temperature in the process of preparing the pigment slurry is preferably 0°C to 100°C.
- the temperature in the pigment surface treatment step is preferably 0°C to 100°C, more preferably 20°C to 80°C.
- the reaction time for pigment surface treatment is preferably 10 minutes to 2 hours.
- iron element When the metal element is an iron element, iron such as iron sulfate, iron chloride, iron fluoride, iron bromide, iron iodide, iron nitrate, iron phosphate, iron borate, iron carbonate, iron acetate, etc. compounds can be used. Iron sulfate, iron chloride, and iron nitrate are preferred from the point of view of economy. As iron, divalent iron or trivalent iron can be used. Also, the iron compound may be either an anhydride or a hydrate.
- oxidizing agent hydrogen peroxide, permanganate, hypochlorous acid, chlorous acid, chloric acid, perchloric acid, peroxodisulfate, chromic acid, dichromic acid, ozone, etc. can be used. can.
- hydrogen peroxide diluted with water to a concentration of 5 to 60% by mass is preferred.
- the amount of the metal compound used is, for example, 3 to 20 parts by weight, preferably 5 to 15 parts by weight, per 100 parts by weight of the azo pigment.
- the amount of the oxidizing agent to be used may be an amount suitable for the oxidation reaction, and varies depending on the concentration, but is, for example, 10 to 100 parts by mass, preferably 20 to 80 parts by mass, with respect to 100 parts by mass of the azo pigment. .
- the metal compound and the oxidizing agent may be added to the pigment slurry at the same time or separately. When they are added at the same time, the metal compound and the oxidizing agent may be mixed in advance and then added. When they are added separately, the metal compound may be added first, or the oxidizing agent may be added first. Also, the oxidizing agent may be added dropwise, or may be added all at once.
- the azo pigment obtained through the above 1) and 2) is further subjected to general pigmentation treatment such as particle size adjustment, pH adjustment, filtration, alcohol washing, water washing, drying, and pulverization as necessary. good too.
- the particle size may be adjusted by heating, stirring, and aging the azo pigment in water and/or an organic solvent under normal pressure or pressure, or by an acid paste method, an acid slurry method, or a dry milling method. , a solvent method, a solvent milling method, or the like.
- the pigment particle surface may be treated with a pigment derivative such as a sulfonic acid pigment derivative, an amino group-containing pigment derivative, or a phthalimidomethyl group-containing pigment derivative, a polymer such as a dispersant, a surfactant, rosin, or the like. These treatments may be performed after or before 2) post-synthesis pigment surface treatment.
- a pigment derivative such as a sulfonic acid pigment derivative, an amino group-containing pigment derivative, or a phthalimidomethyl group-containing pigment derivative
- a polymer such as a dispersant, a surfactant, rosin, or the like.
- An inorganic pigment may be added as necessary to the azo pigment obtained through the above 1) and 2) to obtain the azo pigment of the present invention.
- examples of inorganic pigments include calcium carbonate, magnesium carbonate, precipitated barium sulfate, kaolin, clay, alumina white, and white carbon.
- the ink of the present invention is not particularly limited as long as it contains the azo pigment of the present invention.
- the ink of the present invention can be used for various applications such as offset printing, gravure printing, flexographic printing, screen printing, and inkjet printing. Since the ink of the present invention contains the azo pigment of the present invention, it has a low viscosity and is excellent in pigment dispersibility and transparency. Therefore, the ink of the present invention can be suitably used as a planographic offset ink for planographic offset printing, a liquid ink applicable to gravure printing and flexographic printing, and an inkjet ink.
- offset ink is used for lithographic printing (planographic printing that uses dampening water and waterless lithographic printing that does not use dampening water), letterpress printing, intaglio printing, stencil printing, and ink applied to these plates as a blanket. It refers to ink in various printing methods that combine a transfer (offset) method in which printing is performed on a material to be printed after being transferred to an intermediate transfer body such as.
- the lithographic offset ink contains, in addition to the azo pigment of the present invention, components such as resin varnish, organic solvents, fats and oils such as animal and vegetable oils, and auxiliary agents (drying inhibitors, dryers, rub resistance improvers, etc.).
- the lithographic offset ink is produced by appropriately mixing these components and kneading and dispersing the mixture using a roll mill or the like.
- Ink that can be applied to the lithographic offset printing method is ink having a relatively high viscosity of 5 to 100 Pa ⁇ s.
- resins used in the above resin varnishes include rosin-modified phenolic resins, petroleum resins, petroleum-resin-modified rosin-modified phenolic resins, alkyd resins, rosin esters, vegetable oil-modified rosin-modified phenolic resins, vegetable oil-modified rosin esters, polyesters, and acrylic resins.
- resins include hydrocarbon, alcohol, ester, and ketone solvents commonly used in inks.
- liquid inks used as gravure inks and flexo inks are roughly divided into organic solvent-based liquid inks whose main solvent is organic solvents, and water-based liquid inks whose main solvent is water.
- the azo pigment of the present invention can be applied to both organic solvent-based liquid inks and water-based liquid inks.
- the liquid ink contains, in addition to the azo pigment of the present invention, for example, a binder resin, a solvent, and a dispersant.
- the main component of the solvent is an organic solvent
- the ink is an organic solvent type liquid ink
- the main component of the solvent is a water-miscible organic solvent or an aqueous solvent such as water
- the ink is an aqueous liquid ink.
- Liquid ink is produced by dispersing a mixture of pigment and binder resin with a disperser to obtain a pigment dispersion. Obtained by stirring and mixing.
- the ink viscosity of the liquid ink is preferably in the range of 10 mPa ⁇ s or more from the viewpoint of preventing sedimentation of the pigment and appropriately dispersing the pigment, and 1000 mPa ⁇ s or less from the viewpoint of work efficiency during ink production and printing.
- the binder resin is not particularly limited, and is used in general liquid inks, such as polyurethane resins, acrylic resins, vinyl chloride-vinyl acetate copolymer resins, vinyl chloride-acrylic copolymer resins, and chlorinated polyolefins.
- Resin modified polyolefin resin, cellulose, cellulose derivative, polyamide resin, ethylene-vinyl acetate copolymer resin, vinyl acetate resin, styrene resin, dammar resin, styrene-maleic acid copolymer resin, polyester resin, alkyd resin, polyvinyl chloride Resins, rosin-based resins, rosin-modified maleic acid resins, terpene resins, phenol-modified terpene resins, ketone resins, cyclized rubbers, chlorinated rubbers, butyrals, polyacetal resins, petroleum resins, and modified resins thereof can be used.
- organic solvent examples include aromatic hydrocarbon organic solvents such as toluene, xylene, Solvesso #100, and Solvesso #150; aliphatic hydrocarbon organic solvents such as hexane, methylcyclohexane, heptane, octane, and decane; and methyl acetate.
- aromatic hydrocarbon organic solvents such as toluene, xylene, Solvesso #100, and Solvesso #150
- aliphatic hydrocarbon organic solvents such as hexane, methylcyclohexane, heptane, octane, and decane
- methyl acetate examples include aromatic hydrocarbon organic solvents such as toluene, xylene, Solvesso #100, and Solvesso #150
- aliphatic hydrocarbon organic solvents such as hexane, methylcyclohexane, heptane, octane, and de
- water-miscible organic solvent examples include alcohols such as methanol, ethanol, propanol, butanol and isopropyl alcohol; ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethylene glycol (mono, di)methyl ether, ethylene glycol ( mono, di)ethyl ether, ethylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, monobutyl ether, diethylene glycol (mono, di)methyl ether, diethylene glycol (mono, di)ethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, tri Glycol ethers such as ethylene glycol (mono, di)methyl ether, propylene glycol (mono, di)methyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, and dipropylene glycol (mono
- the ink of the present invention uses the azo pigment of the present invention.
- organic pigments commonly used in inks such as printing inks are used as colorants within a range that does not affect the effects of the present invention.
- a pigment or an inorganic pigment may be used in combination.
- organic pigments examples include phthalocyanine, halogenated phthalocyanine, anthraquinone, anthanthrone, dianthraquinonyl, anthrapyrimidine, perylene, perinone, quinacridone, thioindigo, dioxazine, and isoindolinone pigments.
- the inorganic pigment examples include white pigments such as titanium oxide, zinc oxide, zinc sulfide, barium sulfate, calcium carbonate, chromium oxide, silica, litbon, antimony white, and gypsum.
- inorganic pigments other than the above white pigments include aluminum particles, mica (mica), bronze powder, chrome vermilion, yellow lead, cadmium yellow, cadmium red, ultramarine blue, Prussian blue, red iron oxide, yellow iron oxide, iron black, and zircon. is mentioned.
- various additives such as waxes, chelate cross-linking agents, extender pigments, leveling agents, antifoaming agents, plasticizers, infrared absorbers, ultraviolet absorbers, fragrances, flame retardants, etc. can also contain
- the ink of the present invention is an inkjet ink
- the inkjet ink may be water-based ink or oil-based ink.
- the inkjet ink may be water-based ink or oil-based ink.
- the azo pigment of the present invention has excellent physical properties such as excellent transparency, good dispersibility, and low viscosity, it can be suitably used for various applications other than ink.
- Various uses include paints, coloring agents for plastics, coloring agents for stationery and writing instruments, colored molded articles, textile printing agents, toners, dispersions and resists for color filters, and cosmetics.
- the paint, colorant for plastics, colorant for stationery and writing instruments, textile printing agent, toner, dispersion/resist for color filters, and cosmetics of the present invention contain the azo pigment of the present invention.
- the paint may contain the azo pigment of the present invention as a coloring agent, regardless of the type, synthetic resin paints such as epoxy resins, urethane resins, fluororesins, polyester resins, melamine resins, silicone resins, and acrylic resins, and oil-based paints. , water-based paints, powder paints, nitrate cellulose resin paints (lacquers), and the like. Moreover, it can be used for wood, metal, rubber, plastic, etc., regardless of the application and purpose.
- the above plastic coloring agent may contain the azo pigment of the present invention as a coloring agent, and regardless of the type, it can be used for masterbatches, colored pellets/compounds, dry colors, paste colors, liquid masterbatches, and the like. Further, the colored molded article is obtained by molding a resin containing the coloring agent for plastics.
- the above-mentioned coloring agent for stationery and writing instruments may contain the azo pigment of the present invention as a coloring agent, and can be used for ballpoint pens, markers, colored pencils, paints, crayons, etc. regardless of type.
- the above textile printing agent may contain the azo pigment of the present invention as a coloring agent, regardless of the type or printing method, hand printing (hand printing / turntable), machine printing (flat screen, rotary screen), printing such as dip printing. It can be used for the printing agent of the system. In addition to the above, it may also be used for directly coloring raw materials (undiluted solution, solution, polymer, etc.) of chemical fibers (so-called undiluted solution coloring).
- the above toner may contain the azo pigment of the present invention as a colorant, and is used in laser printers and copiers (especially magenta or yellow for color printing).
- Color filter dispersions and resists are dispersions in which pigments used in color filters such as liquid crystals are dispersed in solvents, or inks containing them and photosensitive agents.
- the resist contains the azo pigment of the present invention as the pigment.
- the above cosmetic may contain the azo pigment of the present invention as a coloring agent, and its type, application and purpose are not limited.
- cosmetics include foundation (face color, concealer, etc.), makeup base (makeup base, pre-makeup, etc.), face powder (face powder), lipstick (lipstick, lip rouge, lip color, lip pencil, lipstick, etc.).
- lip gloss, lip liner, etc. eye makeup (eye shadow, eye color, eyeliner, eyebrow pencil, eyebrow pencil, eyebrow blush, mascara, eyelash cosmetics, etc.), cheek cosmetics (blush, cheek color, cheek rouge, etc.) , nail cosmetics (nail enamel, nail polish, nail color, nail polish, pedicure, nail lacquer, top coat, base coat, etc.), hair coloring (hair dye, hair color spray, hair color stick, color rinse, hair manicure, etc.) is mentioned.
- % means “% by mass” unless otherwise specified.
- IPA isopropanol
- the zeta potential in IPA was measured using a zeta potential/particle size/molecular weight measurement system ELSZ-2000Z (manufactured by Otsuka Electronics Co., Ltd.).
- ELSZ-2000Z manufactured by Otsuka Electronics Co., Ltd.
- 5 mg of a measurement sample and 5 mL of isopropanol were weighed into a 30-mL sample bottle and dispersed for 3 minutes with a desktop ultrasonic cleaner Bransonic M2800-J (manufactured by Branson).
- the ELSZ-2000Z was used to measure the zeta potential in water in the same way as IPA.
- 5 mg of a measurement sample and 5 mL of pure water were weighed into a 30 mL sample bottle and dispersed for 15 minutes with a Bransonic M2800-J.
- 100 ⁇ L of the dispersion liquid of the measurement sample and 10 mL of pure water were weighed into a 30 mL sample bottle and dispersed for 1 minute with a Bransonic M2800-J.
- the prepared measurement solution was injected into the flow cell unit, the cell was installed in ELSZ-2000Z, and the scattering intensity was confirmed.
- the measurement conditions by ELSZ-2000Z were as follows, and the measurement was repeated three times, and the average value was taken as the zeta potential in water of the measurement sample.
- the amount of iron element contained in the azo pigment was measured using an energy dispersive X-ray fluorescent spectrometer, PANalytical Epsilon 5 (manufactured by Spectris Co., Ltd.).
- the element concentration on the surface of the azo pigment particles was measured by the XPS method (X-ray photoelectron spectroscopy). The measurement was performed with an X-ray photoelectron spectrometer Quantera SXM (manufactured by ULVAC-Phi, Inc.). In addition, the value of element concentration was rounded off to two significant digits.
- the coupling reaction was terminated by stirring at 10° C. for 60 minutes to obtain a dye suspension. Subsequently, 77 parts of a 10% Na salt solution of gum rosin (7.7 parts as gum rosin) were added to the resulting dye suspension. After stirring for 30 minutes, a liquid prepared by dissolving 37.4 parts of 72% calcium chloride in 40 parts of water was added, and the mixture was stirred for 60 minutes to complete lake formation. After completion of the lake-forming reaction, the mixture was stirred while being heated at 25° C. for 90 minutes to obtain an aqueous suspension of a calcium lake diazo pigment (C.I. Pigment Red 57:1).
- a calcium lake diazo pigment C.I. Pigment Red 57:1
- Comparative PR57: 1-1′ had a zeta potential of 1.2 mV in isopropanol, a zeta potential of ⁇ 5.1 mV in water, an iron element content of 18 ppm in the azo pigment, and iron on the surface of the azo pigment particles by X-ray photoelectron spectroscopy.
- the element concentration Fe was 0.0 atomic %
- the azo pigment particle surface carbon element concentration C was 67.7 atomic %
- the ratio Fe/C was 0.00.
- Example 1 [Synthesis of PR57:1-1] After dispersing 38.5 parts of 2-amino-5-methylbenzenesulfonic acid in 500 parts of water, 25.0 parts of 35% hydrochloric acid was added, and 36.8 parts of 40% aqueous sodium nitrite solution was added dropwise while maintaining the temperature at 0°C. , to obtain a diazo solution. Next, 42.5 parts of 2-hydroxy-3-naphthoic acid was dispersed in 200 parts of hot water at 50° C., and 74 parts of a 25% aqueous solution of caustic soda was added to obtain a coupler solution. After cooling the coupler solution to 10° C., the above diazo solution was added dropwise while stirring.
- the coupling reaction was terminated by stirring at 10° C. for 60 minutes to obtain a dye suspension. Subsequently, 77 parts of a 10% Na salt solution of gum rosin (7.7 parts as gum rosin) were added to the resulting dye suspension. After stirring for 30 minutes, a liquid prepared by dissolving 37.4 parts of 72% calcium chloride in 40 parts of water was added, and the mixture was stirred for 60 minutes to complete lake formation. After completion of the lake-forming reaction, the mixture was stirred while being heated at 25° C. for 90 minutes to obtain an aqueous suspension of a calcium lake diazo pigment (C.I. Pigment Red 57:1).
- a calcium lake diazo pigment C.I. Pigment Red 57:1
- the pH of the reaction solution was adjusted to 8.0 with a 25% aqueous solution of caustic soda, 120 parts of 35% aqueous calcium chloride solution was added, and the mixture was stirred for 30 minutes, filtered, washed with water, dried at 110°C for a whole day and night, and pulverized.
- PR57:1-1 consisting of Pigment Red 57:1, was obtained.
- the zeta potential in isopropanol of PR57:1-1 is -65.6 mV
- the zeta potential in water is -1.0 mV
- the amount of iron element contained in the azo pigment is 13780 ppm
- the iron element on the surface of the azo pigment particle by X-ray photoelectron spectroscopy The concentration Fe was 0.8 atomic %
- the azo pigment particle surface carbon element concentration C was 65.2 atomic %
- the ratio Fe/C was 0.012.
- Example 2 [Synthesis of PR57:1-2] After dispersing 38.5 parts of 2-amino-5-methylbenzenesulfonic acid in 500 parts of water, 25.0 parts of 35% hydrochloric acid was added, and 36.8 parts of 40% aqueous sodium nitrite solution was added dropwise while maintaining the temperature at 0°C. , to obtain a diazo solution. Next, 42.5 parts of 2-hydroxy-3-naphthoic acid was dispersed in 200 parts of hot water at 50° C., and 74 parts of a 25% aqueous solution of caustic soda was added to obtain a coupler solution. After cooling the coupler solution to 10° C., the above diazo solution was added dropwise while stirring.
- the coupling reaction was terminated by stirring at 10° C. for 60 minutes to obtain a dye suspension. Subsequently, 77 parts of a 10% Na salt solution of gum rosin (7.7 parts as gum rosin) were added to the resulting dye suspension. After stirring for 30 minutes, a solution obtained by dissolving 37.4 parts of 72% calcium chloride in 40 parts of water and 6.0 parts of iron (II) sulfate heptahydrate were added, and the mixture was stirred for 60 minutes to complete lake formation. . After completion of the lake-forming reaction, the mixture was stirred while being heated at 25° C. for 90 minutes to obtain an aqueous suspension of a calcium lake diazo pigment (C.I. Pigment Red 57:1).
- a calcium lake diazo pigment C.I. Pigment Red 57:1
- the zeta potential in isopropanol of PR57:1-2 is -33.0 mV
- the amount of iron element contained in the azo pigment is 630 ppm
- the iron element concentration Fe on the surface of the azo pigment particle by X-ray photoelectron spectroscopy is 0.0 atomic%
- the azo pigment The particle surface carbon element concentration C was 66.8 atomic %
- the ratio Fe/C was 0.00.
- Comparative PR146-1′ had a zeta potential of ⁇ 26.0 mV in isopropanol, a zeta potential of ⁇ 33.1 mV in water, an iron element content of 61 ppm in the azo pigment, and an iron element on the surface of the azo pigment particles by X-ray photoelectron spectroscopy.
- the concentration Fe was 0.0 atomic %
- the azo pigment particle surface carbon element concentration C was 77.7 atomic %
- the ratio Fe/C was 0.00.
- the zeta potential of PR146-1 in isopropanol is -46.3 mV
- the zeta potential in water is -30.5 mV
- the amount of iron element contained in the azo pigment is 1250 ppm
- the iron element concentration Fe on the surface of the azo pigment particle by X-ray photoelectron spectroscopy. was 0.1 atomic %
- the azo pigment particle surface carbon element concentration C was 77.3 atomic %
- the ratio Fe/C was 0.0013.
- the zeta potential of PR146-2 in isopropanol is -68.5 mV
- the zeta potential in water is -36.4 mV
- the amount of iron element contained in the azo pigment is 5900 ppm
- the iron element concentration Fe on the surface of the azo pigment particle by X-ray photoelectron spectroscopy. was 0.3 atomic %
- the azo pigment particle surface carbon element concentration C was 76.7 atomic %
- the ratio Fe/C was 0.0039.
- Comparative PY13-1′ had a zeta potential in isopropanol of 5.7 mV, an iron element content of the azo pigment of 250 ppm, an iron element concentration Fe on the surface of the azo pigment particles determined by X-ray photoelectron spectroscopy, of 0.0 atomic%, and azo pigment particles.
- the surface carbon element concentration C was 76.5 atomic %, and the ratio Fe/C was 0.00.
- Comparative PY83-1′ had a zeta potential in isopropanol of 17.3 mV, an iron element content of the azo pigment of 185 ppm, an iron element concentration Fe on the surface of the azo pigment particles determined by X-ray photoelectron spectroscopy of 0.0 atomic%, and azo pigment particles.
- the surface carbon element concentration C was 67.5 atomic %, and the ratio Fe/C was 0.00.
- a comparative PY83-2' consisting of Pigment Yellow 83 was obtained.
- the zeta potential in isopropanol of comparative PY83-2′ is 10.8 mV
- the amount of iron element contained in the azo pigment is 58 ppm
- the iron element concentration Fe on the surface of the azo pigment particle measured by X-ray photoelectron spectroscopy is 0.0 atomic%
- the azo pigment particle was 67.6 atomic %
- the ratio Fe/C was 0.00.
- the zeta potential of PY83-1 in isopropanol is ⁇ 42.2 mV
- the amount of iron element contained in the azo pigment is 3480 ppm
- the iron element concentration Fe on the surface of the azo pigment particle by X-ray photoelectron spectroscopy is 0.1 atomic%
- the surface of the azo pigment particle The carbon element concentration C was 67.1 atomic %
- the ratio Fe/C was 0.0015.
- a comparative PO13-1' consisting of Pigment Orange 13 was obtained.
- the zeta potential in isopropanol of comparative PO13-1′ is ⁇ 25.5 mV
- the amount of iron element contained in the azo pigment is 87 ppm
- the iron element concentration Fe on the surface of the azo pigment particle measured by X-ray photoelectron spectroscopy is 0.0 atomic%
- the azo pigment The particle surface carbon element concentration C was 73.5 atomic %, and the ratio Fe/C was 0.00.
- a comparative PY55-1' consisting of Pigment Yellow 55 was obtained.
- the zeta potential in isopropanol of comparative PY55-1′ is ⁇ 29.5 mV
- the amount of iron element contained in the azo pigment is 124 ppm
- the iron element concentration Fe on the surface of the azo pigment particle measured by X-ray photoelectron spectroscopy is 0.0 atomic%
- the azo pigment The particle surface carbon element concentration C was 73.5 atomic %, and the ratio Fe/C was 0.00.
- a dry pigment mass consisting of Pigment Yellow 180 was obtained. 60 parts of this dry pigment mass, 340 parts of sodium chloride and 70 parts of diethylene glycol were charged into a 1 L double-arm kneader (manufactured by Yoshida Seisakusho Co., Ltd.) and ground at 80° C. for 5 hours.
- the resulting ground kneaded product was added to 2,000 parts of water, heated to 60° C., stirred for 1 hour, filtered, washed with water, and subjected to C.I. I.
- a wet cake of Pigment Yellow 180 was obtained. After drying the wet cake at 110° C. for a whole day and night, it was pulverized to give C.I. I.
- a comparative PY180-1' consisting of Pigment Yellow 180 was obtained.
- Comparative PY180-1′ had a zeta potential of ⁇ 12.4 mV in isopropanol, a zeta potential of ⁇ 34.9 mV in water, an iron element content of 455 ppm in the azo pigment, and an iron element on the surface of the azo pigment particles by X-ray photoelectron spectroscopy.
- the concentration Fe was 0.0 atomic %
- the azo pigment particle surface carbon element concentration C was 69.2 atomic %
- the ratio Fe/C was 0.00.
- a dry pigment mass consisting of Pigment Yellow 180 was obtained. 60 parts of this dry pigment mass, 340 parts of sodium chloride and 70 parts of diethylene glycol were charged into a 1 L double-arm kneader (manufactured by Yoshida Seisakusho Co., Ltd.) and ground at 80° C. for 5 hours.
- the resulting ground kneaded product was added to 2,000 parts of water, heated to 60° C., stirred for 1 hour, filtered, washed with water, and subjected to C.I.
- a wet cake of Pigment Yellow 180 was obtained. The wet cake is added to 1000 parts of water and stirred for 1 hour. Next, 70 parts of 35% hydrogen peroxide was added, and the mixture was further stirred for 2 hours, filtered, washed with water, dried at 110°C for one day and night, and pulverized.
- a comparative PY180-2' consisting of Pigment Yellow 180 was obtained.
- the zeta potential in isopropanol of comparative PY180-2′ is ⁇ 18.5 mV
- the amount of iron element contained in the azo pigment is 434 ppm
- the iron element concentration Fe on the surface of the azo pigment particle measured by X-ray photoelectron spectroscopy is 0.0 atomic%
- the azo pigment The particle surface carbon element concentration C was 68.5 atomic %, and the ratio Fe/C was 0.00.
- a dry pigment mass consisting of Pigment Yellow 180 was obtained. 60 parts of this dry pigment mass, 340 parts of sodium chloride and 70 parts of diethylene glycol were charged into a 1 L double-arm kneader (manufactured by Yoshida Seisakusho Co., Ltd.) and ground at 80° C. for 5 hours.
- the zeta potential of PY180-1 in isopropanol is -38.8 mV
- the zeta potential in water is -36.4 mV
- the amount of iron element contained in the azo pigment is 4460 ppm
- the iron element concentration Fe on the surface of the azo pigment particle by X-ray photoelectron spectroscopy. was 0.1 atomic %
- the azo pigment particle surface carbon element concentration C was 67.4 atomic %
- the ratio Fe/C was 0.0015.
- Comparative PR213-1′ had a zeta potential in isopropanol of 27.1 mV, an iron element content of the azo pigment of 16 ppm, an iron element concentration Fe on the surface of the azo pigment particles determined by X-ray photoelectron spectroscopy, of 0.0 atomic%, and azo pigment particles.
- the surface carbon element concentration C was 75.1 atomic %, and the ratio Fe/C was 0.00.
- the zeta potential in isopropanol of PR213-1 is -38.8 mV
- the amount of iron element contained in the azo pigment is 505 ppm
- the iron element concentration Fe on the surface of the azo pigment particle by X-ray photoelectron spectroscopy is 0.1 atomic%
- the surface of the azo pigment particle The carbon element concentration C was 74.3 atomic %
- the ratio Fe/C was 0.0013.
- the zeta potential in isopropanol of Comparative PO64-1′ is 2.7 mV
- the amount of iron element contained in the azo pigment is 20 ppm
- the iron element concentration Fe on the surface of the azo pigment particle measured by X-ray photoelectron spectroscopy is 0.0 atomic%
- the azo pigment particle The surface carbon element concentration C was 59.4 atomic %, and the ratio Fe/C was 0.00.
- the zeta potential of PO64-1 in isopropanol is -41.0 mV
- the amount of iron element contained in the azo pigment is 6390 ppm
- the iron element concentration Fe on the surface of the azo pigment particle by X-ray photoelectron spectroscopy is 0.1 atomic%
- the surface of the azo pigment particle The carbon element concentration C was 58.1 atomic %
- the ratio Fe/C was 0.0017.
- the obtained polyurethane ink was applied to PET film Lumirror 50T-60 (manufactured by Panac Industries Co., Ltd.). It was developed with a No. 6 bar coater. The developed surface of the developed film was placed face down on black paper, and the transparency was determined visually. Transparency is judged on a scale of 1 to 9, with a higher number indicating higher transparency and a lower number indicating opacity. The higher the transparency, the better.
- Table 1 shows the obtained viscosity of each polyurethane ink and the transparency evaluation of the spread film.
- the azo pigments of Examples 1 to 11 of the present invention are superior in transparency, low in viscosity, and excellent in dispersibility compared to conventionally known azo pigments having the same structure. Therefore, the azo pigment of the present invention is suitable as ink (especially printing ink).
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Abstract
Description
顔料粒子はナノレベルの粒子(一次粒子)であるが、粒子間のファンデルワールス力のため一次粒子が凝集し、二次粒子を形成している。顔料を着色成分とするインキを作製する際、分散工程により顔料の二次粒子を一次粒子まで解砕するが、何の工夫もないと粒子間の引力により一次粒子が再凝集してしまう。凝集体は粗大であるため光を散乱させる作用が強く、透明性を落とす原因となる。さらに、凝集体の形成により顔料粒子の運動性が失われ、粒子の間隙に溶媒分子が固定化されるため、粘度が増大する。ここで、IPA中で特定のゼータ電位を持つ顔料を用いる。すると、顔料粒子の電気二重層の反発から粒子同士の接近が抑えられて凝集が防がれるので、良好な分散性・透明性が得られる。顔料粒子に絶対値の大きなゼータ電位を与えるには、粒子表面に何らかの方法で電荷を持つ物質を存在させる必要がある。もっとも単純な方法は、金属塩などイオン性の物質を処理する方法であるが、単に金属塩と顔料を混合するのみでは、顔料粒子から簡単に塩が流出してしまう。そこで、顔料と金属塩の共存下、酸化剤により金属を酸化させ、顔料粒子表面に金属を処理することにした。金属と酸化剤は選択肢が豊富であり、安価な化合物を選択すれば、経済的に有利である。金属と酸化剤との反応は複雑であるため、金属がどのような化合物となっているのか特定することは難しいが、例えば金属が鉄である場合、酸化鉄やオキシ水酸化鉄となっていると推定する。こうして顔料表面上に金属が存在することで、IPA中で特定のゼータ電位を与える。本発明では、顔料粒子の表面に金属が存在することが重要であり、顔料の構造中に金属元素が含まれるのみでは不十分で、顔料表面に金属が露出していなければ、高い透明性と分散性は得られない。
『項1. イソプロパノール(IPA)中のゼータ電位が-80mV~-30mVであるアゾ顔料。
項2. 前記アゾ顔料100質量部あたり金属元素を0.05~2.00質量部含む項1に記載のアゾ顔料。
項3. 前記金属元素が鉄元素である項2に記載のアゾ顔料。
項4. X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Fe(atomic%)と、アゾ顔料粒子表面炭素元素濃度C(atomic%)の比(Fe/C)が0.20以下である項3に記載のアゾ顔料。
項5. 項1~4のいずれか1項に記載のアゾ顔料を含有するインキ。
項6. 項1~4のいずれか1項に記載のアゾ顔料を含有する塗料、プラスチック用着色剤、着色成形品、文具・筆記具用着色剤、捺染剤、トナー、カラーフィルタ用分散液・レジスト、及び化粧料。』に関する。
本発明のアゾ顔料は、イソプロパノール(IPA)中のゼータ電位が-80mV~-30mVである。当該ゼータ電位は、好ましくは-70mV~-35mV、より好ましくは-60mV~-40mVである。IPA中のゼータ電位がこの範囲にあることで、透明性に優れ、分散性が良く、低粘度となる。また、本発明のアゾ顔料は、水中のゼータ電位が例えば-50mV~50mV、好ましくは-25mV~25mV、より好ましくは-10mV~10mVである。ゼータ電位は、電気泳動光散乱測定法によりゼータ電位・粒径・分子量測定システムにて測定することができる。
本発明のアゾ顔料は、例えば、1)アゾ顔料の合成、及び2)合成後の顔料表面処理を経て得られる。まず、1)アゾ顔料の合成は、芳香族アミンジアゾニウム塩からなるジアゾ成分と、ジアゾニウム塩を構成する芳香族アミン以外の芳香族化合物からなるカップラー成分とをカップリングすることにより合成できる。ジアゾ成分である芳香族アミンジアゾニウム塩は、芳香族アミンを塩酸で酸性とし、亜硝酸ナトリウム水溶液を添加することで得られる。また、ジアゾ成分とカップラー成分とのカップリングは、水酸化ナトリウムなどを用いたアルカリ条件で行われる。カップリング後に得られたアゾ化合物が溶性アゾ(染料)である場合、カルシウム、バリウムなどの金属塩類の水溶液を加えて不溶化することにより金属でレーキ化されたアゾ顔料としてもよい。1)アゾ顔料の合成では、上記のようにカップリング反応により合成するのではなく、市販のアゾ顔料をそのまま用いてもよい。
本発明のインキは、上記本発明のアゾ顔料を含む限り特に制限されない。本発明のインキは、オフセット印刷、グラビア印刷、フレキソ印刷、スクリーン印刷、インクジェット方式での印刷等の各種用途に用いることができる。本発明のインキは、上記本発明のアゾ顔料を含むため、低粘度であり、顔料の分散性や透明性に優れる。よって、本発明のインキは、平版オフセット印刷用の平版オフセットインキ、グラビア印刷用やフレキソ印刷用に適用できるリキッドインキ、インクジェットインキとして好適に使用することができる。
本発明のアゾ顔料は、透明性に優れ、分散性が良く、低粘度であるという優れた物性を有するため、インキ以外の各種用途にも好適に用いることができる。各種用途としては、塗料、プラスチック用着色剤、文具・筆記具用着色剤、着色成形品、捺染剤、トナー、カラーフィルタ用分散液・レジスト、及び化粧料が挙げられる。本発明の塗料、プラスチック用着色剤、文具・筆記具用着色剤、捺染剤、トナー、カラーフィルタ用分散液・レジスト、及び化粧料は、本発明のアゾ顔料を含む。
測定温度:25℃
測定待ち時間:300秒
ピンホール:50
積算回数:10回
セル測定位置:0.70/0.35/0.00/-0.35/-0.70
印可電圧:Fixed
印可電圧(固定):100
印可電圧波形タイプ:Auto
定電流:51mA
ローレンツフィット:1peak
ゼータ電位換算式:Huckel
測定温度:25℃
測定待ち時間:300秒
ピンホール:50
積算回数:10回
セル測定位置:0.70/0.35/0.00/-0.35/-0.70
印可電圧:Fixed
印可電圧(固定):60
印可電圧波形タイプ:Auto
定電流:51mA
ローレンツフィット:1peak
ゼータ電位換算式:Smoluchows
X線源:AlKα(モノクロメータ)
測定:ポイント測定(100μm),表面
測定回数:3回
帯電補正:C1s=284.8eV
2-アミノ-5-メチルベンゼンスルホン酸38.5部を水500部に分散後、35%塩酸25.0部を加え、0℃に保ちながら40%亜硝酸ソーダ水溶液36.8部を滴下し、ジアゾ溶液を得た。次に、2-ヒドロキシ-3-ナフトエ酸42.5部を50℃の温水200部に分散後、25%苛性ソーダ水溶液74部を加えてカップラー溶液を得た。カップラー溶液を10℃まで冷却後、撹拌しながら上記ジアゾ溶液を滴下した。10℃で60分間撹拌してカップリング反応を終了させ、染料懸濁液を得た。続いて、得られた染料懸濁液に、10%のガムロジンのNa塩溶液77部(ガムロジンとして7.7部)を添加した。30分撹拌後、72%塩化カルシウム37.4部を水40部に溶解した液を加え、60分撹拌してレーキ化を終了させた。レーキ化反応終了後、25℃で90分間加熱しつつ撹拌し、カルシウムレーキアゾ顔料(C.I.ピグメントレッド57:1)の水中懸濁液を得た。この懸濁液を85℃まで加熱後、90分間撹拌した後、濾過、水洗し、C.I.ピグメントレッド57:1のウェットケーキを得た。このウェットケーキを110℃で一昼夜乾燥させた後、粉砕して、C.I.ピグメントレッド57:1からなる比較PR57:1-1’を得た。比較PR57:1-1’のイソプロパノール中のゼータ電位は1.2mV、水中のゼータ電位は-5.1mV、アゾ顔料に含まれる鉄元素量は18ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.0atomic%、アゾ顔料粒子表面炭素元素濃度Cは67.7atomic%、その比Fe/Cは0.00だった。
2-アミノ-5-メチルベンゼンスルホン酸38.5部を水500部に分散後、35%塩酸25.0部を加え、0℃に保ちながら40%亜硝酸ソーダ水溶液36.8部を滴下し、ジアゾ溶液を得た。次に、2-ヒドロキシ-3-ナフトエ酸42.5部を50℃の温水200部に分散後、25%苛性ソーダ水溶液74部を加えてカップラー溶液を得た。カップラー溶液を10℃まで冷却後、撹拌しながら上記ジアゾ溶液を滴下した。10℃で60分間撹拌してカップリング反応を終了させ、染料懸濁液を得た。続いて、得られた染料懸濁液に、10%のガムロジンのNa塩溶液77部(ガムロジンとして7.7部)を添加した。30分撹拌後、72%塩化カルシウム37.4部を水40部に溶解した液を加え、60分撹拌してレーキ化を終了させた。レーキ化反応終了後、25℃で90分間加熱しつつ撹拌し、カルシウムレーキアゾ顔料(C.I.ピグメントレッド57:1)の水中懸濁液を得た。この懸濁液を85℃まで加熱後、90分間撹拌した後、濾過、水洗し、C.I.ピグメントレッド57:1のウェットケーキを得た。このウェットケーキを水2500部に加え、1時間撹拌する。次いで、硫酸鉄(II)七水和物12.0部を加え、30分間撹拌し、35%過酸化水素37.5部を加え、さらに2時間撹拌する。反応液のpHを25%苛性ソーダ水溶液で8.0に調整し、35%塩化カルシウム水を120部加え、30分間撹拌した後、濾過、水洗、110℃で一昼夜乾燥、粉砕して、C.I.ピグメントレッド57:1からなるPR57:1-1を得た。PR57:1-1のイソプロパノール中のゼータ電位は-65.6mV、水中のゼータ電位は-1.0mV、アゾ顔料に含まれる鉄元素量は13780ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.8atomic%、アゾ顔料粒子表面炭素元素濃度Cは65.2atomic%、その比Fe/Cは0.012だった。
2-アミノ-5-メチルベンゼンスルホン酸38.5部を水500部に分散後、35%塩酸25.0部を加え、0℃に保ちながら40%亜硝酸ソーダ水溶液36.8部を滴下し、ジアゾ溶液を得た。次に、2-ヒドロキシ-3-ナフトエ酸42.5部を50℃の温水200部に分散後、25%苛性ソーダ水溶液74部を加えてカップラー溶液を得た。カップラー溶液を10℃まで冷却後、撹拌しながら上記ジアゾ溶液を滴下した。10℃で60分間撹拌してカップリング反応を終了させ、染料懸濁液を得た。続いて、得られた染料懸濁液に、10%のガムロジンのNa塩溶液77部(ガムロジンとして7.7部)を添加した。30分撹拌後、72%塩化カルシウム37.4部を水40部に溶解した液と、硫酸鉄(II)七水和物6.0部を加え、60分撹拌してレーキ化を終了させた。レーキ化反応終了後、25℃で90分間加熱しつつ撹拌し、カルシウムレーキアゾ顔料(C.I.ピグメントレッド57:1)の水中懸濁液を得た。この懸濁液を85℃まで加熱後、35%過酸化水素37.5部を加え、90分間撹拌した後、濾過、水洗し、C.I.ピグメントレッド57:1のウェットケーキを得た。このウェットケーキを110℃で一昼夜乾燥させた後、粉砕して、C.I.ピグメントレッド57:1からなるPR57:1-2を得た。PR57:1-2のイソプロパノール中のゼータ電位は-33.0mV、アゾ顔料に含まれる鉄元素量は630ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.0atomic%、アゾ顔料粒子表面炭素元素濃度Cは66.8atomic%、その比Fe/Cは0.00だった。
N-(4-クロロ-2,5ジメトキシフェニル)-3-ヒドロキシ-2-ナフトアミド12.5部を50℃の温水200部に投入した後、ロート油0.6部、25%苛性ソーダ水液16部を加えてカップラー溶液を得た。次に、3-アミノ-4-メトキシベンズアニリド8.0部を水100部に分散後、35%塩酸10部を加え、0℃に保ちながら40%亜硝酸ソーダ水溶液6部を滴下し、ジアゾ溶液を得た。このジアゾ溶液にカップラー溶液を添加した後、85℃まで加熱し、60分間撹拌した後、濾過、水洗し、C.I.ピグメントレッド146のウェットケーキを得た。このウェットケーキを110℃で一昼夜乾燥させた後、粉砕して、C.I.ピグメントレッド146からなる比較PR146-1’を得た。比較PR146-1’のイソプロパノール中のゼータ電位は-26.0mV、水中のゼータ電位は-33.1mV、アゾ顔料に含まれる鉄元素量は61ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.0atomic%、アゾ顔料粒子表面炭素元素濃度Cは77.7atomic%、その比Fe/Cは0.00だった。
N-(4-クロロ-2,5ジメトキシフェニル)-3-ヒドロキシ-2-ナフトアミド12.5部を50℃の温水200部に投入した後、ロート油0.6部、25%苛性ソーダ水液16部を加えてカップラー溶液を得た。次に、3-アミノ-4-メトキシベンズアニリド8.0部を水100部に分散後、35%塩酸10部を加え、0℃に保ちながら40%亜硝酸ソーダ水溶液6部を滴下し、ジアゾ溶液を得た。このジアゾ溶液にカップラー溶液を添加した後、85℃まで加熱し、60分間撹拌した後、濾過、水洗し、C.I.ピグメントレッド146のウェットケーキを得た。このウェットケーキを水500部に加え、1時間撹拌する。次いで、硫酸鉄(II)七水和物0.58部を加え、30分間撹拌し、35%過酸化水素18.0部を加え、さらに2時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥、粉砕して、C.I.ピグメントレッド146からなるPR146-1を得た。PR146-1のイソプロパノール中のゼータ電位は-46.3mV、水中のゼータ電位は-30.5mV、アゾ顔料に含まれる鉄元素量は1250ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.1atomic%、アゾ顔料粒子表面炭素元素濃度Cは77.3atomic%、その比Fe/Cは0.0013だった。
N-(4-クロロ-2,5ジメトキシフェニル)-3-ヒドロキシ-2-ナフトアミド12.5部を50℃の温水200部に投入した後、ロート油0.6部、25%苛性ソーダ水液16部を加えてカップラー溶液を得た。次に、3-アミノ-4-メトキシベンズアニリド8.0部を水100部に分散後、35%塩酸10部を加え、0℃に保ちながら40%亜硝酸ソーダ水溶液6部を滴下し、ジアゾ溶液を得た。このジアゾ溶液にカップラー溶液を添加した後、85℃まで加熱し、60分間撹拌した後、濾過、水洗し、C.I.ピグメントレッド146のウェットケーキを得た。このウェットケーキを水500部に加え、1時間撹拌する。次いで、硫酸鉄(II)七水和物0.58部を加え、30分間撹拌し、35%過酸化水素18.0部を加え、さらに2時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥、粉砕して、C.I.ピグメントレッド146からなるPR146-2を得た。PR146-2のイソプロパノール中のゼータ電位は-68.5mV、水中のゼータ電位は-36.4mV、アゾ顔料に含まれる鉄元素量は5900ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.3atomic%、アゾ顔料粒子表面炭素元素濃度Cは76.7atomic%、その比Fe/Cは0.0039だった。
3,3’-ジクロロベンジジンの塩酸塩(3,3’-ジクロロベンジジン250部に相当する量)と35%塩酸316部を水4000部に加え、0℃に冷却後、40%亜硝酸ソーダ水溶液358部を加え、1時間撹拌する。ここに10%スルファミン酸80部を加え、過剰の亜硝酸ソーダを消失させ、3,3’-ジクロロベンジジンのテトラゾ溶液を得た。これとは別に、水7500部にアセト酢酸-m-キシリダイド435部と25%苛性ソーダ水溶液350部を加えて撹拌、溶解させ、次いで10%酢酸1500部を少しずつ加えてカップラー懸濁液とする。次いで、カップラー懸濁液にテトラゾ溶液を15~17℃に保ちながら2時間かけて加える。さらに1時間撹拌後、90℃まで加熱し、2時間撹拌し、濾過、水洗して、C.I.ピグメントイエロー13のウェットケーキを得た。このウェットケーキを110℃で一昼夜乾燥させた後、粉砕して、C.I.ピグメントイエロー13からなる比較PY13-1’を得た。比較PY13-1’のイソプロパノール中のゼータ電位は5.7mV、アゾ顔料に含まれる鉄元素量は250ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.0atomic%、アゾ顔料粒子表面炭素元素濃度Cは76.5atomic%、その比Fe/Cは0.00だった。
3,3’-ジクロロベンジジンの塩酸塩(3,3’-ジクロロベンジジン250部に相当する量)と35%塩酸316部を水4000部に加え、0℃に冷却後、40%亜硝酸ソーダ水溶液358部を加え、1時間撹拌する。ここに10%スルファミン酸80部を加え、過剰の亜硝酸ソーダを消失させ、3,3’-ジクロロベンジジンのテトラゾ溶液を得た。これとは別に、水7500部にアセト酢酸-m-キシリダイド435部と25%苛性ソーダ水溶液350部を加えて撹拌、溶解させ、次いで10%酢酸1500部を少しずつ加えてカップラー懸濁液とする。次いで、カップラー懸濁液にテトラゾ溶液を15~17℃に保ちながら2時間かけて加える。さらに1時間撹拌後、90℃まで加熱し、2時間撹拌し、濾過、水洗して、C.I.ピグメントイエロー13のウェットケーキを得た。このウェットケーキを水10000部に加え、1時間撹拌する。次いで、硫酸鉄(II)七水和物43.0部を加え、30分間撹拌し、35%過酸化水素1000部を加え、さらに2時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥、粉砕して、C.I.ピグメントイエロー13からなるPY13-1を得た。PY13-1のイソプロパノール中のゼータ電位は-45.1mV、アゾ顔料に含まれる鉄元素量は4870ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.2atomic%、アゾ顔料粒子表面炭素元素濃度Cは75.9atomic%、その比Fe/Cは0.0026だった。
3,3’-ジクロロベンジジンの塩酸塩(3,3’-ジクロロベンジジン21.8部に相当する量)と35%塩酸34.3部を水350部に加え、0℃に冷却後、40%亜硝酸ソーダ水溶液31.4部を加え、1時間撹拌する。ここに10%スルファミン酸7.6部を加え、過剰の亜硝酸ソーダを消失させ、3,3’-ジクロロベンジジンのテトラゾ溶液を得た。これとは別に、水400部に4’-クロロ-2’,5’-ジメトキシアセトアセトアニリド49.9部と25%苛性ソーダ水溶液48.0部を加えて撹拌、溶解させ、液量を水で500部に調整し、カップラー溶液を得た。次いで、撹拌機を有する反応容器に水800部、酢酸5.3部を加え、20℃に保ちながら撹拌し、さらに前記カップラー溶液の一部を加え、pH5.5に調整した。ここに、テトラゾ溶液とカップラー溶液を同時に3時間で滴下した。このとき、反応液温度が20℃、pHが5.4~5.6を維持するよう適時氷または5%苛性ソーダ水溶液を添加した。全てのテトラゾ溶液とカップラー溶液を滴下後、5%苛性ソーダ水溶液によりpH11.0に調整し、90℃まで加熱、40分間撹拌した。その後、70℃まで冷却し、35%塩酸でpH6.5に調整して10分間撹拌後、濾過、水洗して、C.I.ピグメントイエロー83のウェットケーキを得た。このウェットケーキを110℃で一昼夜乾燥させた後、粉砕して、C.I.ピグメントイエロー83からなる比較PY83-1’を得た。比較PY83-1’のイソプロパノール中のゼータ電位は17.3mV、アゾ顔料に含まれる鉄元素量は185ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.0atomic%、アゾ顔料粒子表面炭素元素濃度Cは67.5atomic%、その比Fe/Cは0.00だった。
3,3’-ジクロロベンジジンの塩酸塩(3,3’-ジクロロベンジジン21.8部に相当する量)と35%塩酸34.3部を水350部に加え、0℃に冷却後、40%亜硝酸ソーダ水溶液31.4部を加え、1時間撹拌する。ここに10%スルファミン酸7.6部を加え、過剰の亜硝酸ソーダを消失させ、3,3’-ジクロロベンジジンのテトラゾ溶液を得た。これとは別に、水400部に4’-クロロ-2’,5’-ジメトキシアセトアセトアニリド49.9部と25%苛性ソーダ水溶液48.0部を加えて撹拌、溶解させ、液量を水で500部に調整し、カップラー溶液を得た。次いで、撹拌機を有する反応容器に水800部、酢酸5.3部を加え、20℃に保ちながら撹拌し、さらに前記カップラー溶液の一部を加え、pH5.5に調整した。ここに、テトラゾ溶液とカップラー溶液を同時に3時間で滴下した。このとき、反応液温度が20℃、pHが5.4~5.6を維持するよう適時氷または5%苛性ソーダ水溶液を添加した。全てのテトラゾ溶液とカップラー溶液を滴下後、5%苛性ソーダ水溶液によりpH11.0に調整し、90℃まで加熱、40分間撹拌した。その後、70℃まで冷却し、35%塩酸でpH6.5に調整して10分間撹拌後、濾過、水洗して、C.I.ピグメントイエロー83のウェットケーキを得た。このウェットケーキを水1500部に加え、1時間撹拌する。次いで、35%過酸化水素100部を加え、さらに2時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥、粉砕して、C.I.ピグメントイエロー83からなる比較PY83-2’を得た。比較PY83-2’のイソプロパノール中のゼータ電位は10.8mV、アゾ顔料に含まれる鉄元素量は58ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.0atomic%、アゾ顔料粒子表面炭素元素濃度Cは67.6atomic%、その比Fe/Cは0.00だった。
3,3’-ジクロロベンジジンの塩酸塩(3,3’-ジクロロベンジジン21.8部に相当する量)と35%塩酸34.3部を水350部に加え、0℃に冷却後、40%亜硝酸ソーダ水溶液31.4部を加え、1時間撹拌する。ここに10%スルファミン酸7.6部を加え、過剰の亜硝酸ソーダを消失させ、3,3’-ジクロロベンジジンのテトラゾ溶液を得た。これとは別に、水400部に4’-クロロ-2’,5’-ジメトキシアセトアセトアニリド49.9部と25%苛性ソーダ水溶液48.0部を加えて撹拌、溶解させ、液量を水で500部に調整し、カップラー溶液を得た。次いで、撹拌機を有する反応容器に水800部、酢酸5.3部を加え、20℃に保ちながら撹拌し、さらに前記カップラー溶液の一部を加え、pH5.5に調整した。ここに、テトラゾ溶液とカップラー溶液を同時に3時間で滴下した。このとき、反応液温度が20℃、pHが5.4~5.6を維持するよう適時氷または5%苛性ソーダ水溶液を添加した。全てのテトラゾ溶液とカップラー溶液を滴下後、5%苛性ソーダ水溶液によりpH11.0に調整し、90℃まで加熱、40分間撹拌した。その後、70℃まで冷却し、35%塩酸でpH6.5に調整して10分間撹拌後、濾過、水洗して、C.I.ピグメントイエロー83のウェットケーキを得た。このウェットケーキを水1500部に加え、1時間撹拌する。次いで、硫酸鉄(II)七水和物3.0部を加え、30分間撹拌し、35%過酸化水素100部を加え、さらに2時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥、粉砕して、C.I.ピグメントイエロー83からなるPY83-1を得た。PY83-1のイソプロパノール中のゼータ電位は-42.2mV、アゾ顔料に含まれる鉄元素量は3480ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.1atomic%、アゾ顔料粒子表面炭素元素濃度Cは67.1atomic%、その比Fe/Cは0.0015だった。
3,3’-ジクロロベンジジンの塩酸塩(3,3’-ジクロロベンジジン300部に相当する量)と35%塩酸420部を水4000部に加え、0℃に冷却後、40%亜硝酸ソーダ水溶液430部を加え、1時間撹拌する。ここに10%スルファミン酸100部を加え、過剰の亜硝酸ソーダを消失させ、3,3’-ジクロロベンジジンのテトラゾ溶液を得た。これとは別に、水7500部に3-メチル-1-フェニル-5-ピラゾロン427部と25%苛性ソーダ水溶液520部を加えて撹拌、溶解させ、次いで10%酢酸3000部を少しずつ加え、20%苛性ソーダ水溶液でpH6.5に調整してカップラー懸濁液とする。続いて、カップラー懸濁液にテトラゾ溶液を30~40℃に保ちながら加え、さらに30分間撹拌後、90℃まで加熱し、30分間撹拌、濾過、水洗して、C.I.ピグメントオレンジ13のウェットケーキを得た。このウェットケーキを110℃で一昼夜乾燥させた後、粉砕して、C.I.ピグメントオレンジ13からなる比較PO13-1’を得た。比較PO13-1’のイソプロパノール中のゼータ電位は-25.5mV、アゾ顔料に含まれる鉄元素量は87ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.0atomic%、アゾ顔料粒子表面炭素元素濃度Cは73.5atomic%、その比Fe/Cは0.00だった。
3,3’-ジクロロベンジジンの塩酸塩(3,3’-ジクロロベンジジン300部に相当する量)と35%塩酸420部を水4000部に加え、0℃に冷却後、40%亜硝酸ソーダ水溶液430部を加え、1時間撹拌する。ここに10%スルファミン酸100部を加え、過剰の亜硝酸ソーダを消失させ、3,3’-ジクロロベンジジンのテトラゾ溶液を得た。これとは別に、水7500部に3-メチル-1-フェニル-5-ピラゾロン427部と25%苛性ソーダ水溶液520部を加えて撹拌、溶解させ、次いで10%酢酸3000部を少しずつ加え、20%苛性ソーダ水溶液でpH6.5に調整してカップラー懸濁液とする。続いて、カップラー懸濁液にテトラゾ溶液を30~40℃に保ちながら加え、さらに30分間撹拌後、90℃まで加熱し、30分間撹拌、濾過、水洗して、C.I.ピグメントオレンジ13のウェットケーキを得た。このウェットケーキを水10000部に加え、1時間撹拌する。次いで、硫酸鉄(II)七水和物43.0部を加え、30分間撹拌し、35%過酸化水素1000部を加え、さらに2時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥、粉砕して、C.I.ピグメントオレンジ13からなるPO13-1を得た。PO13-1のイソプロパノール中のゼータ電位は-45.8mV、アゾ顔料に含まれる鉄元素量は4890ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.1atomic%、アゾ顔料粒子表面炭素元素濃度Cは71.7atomic%、その比Fe/Cは0.0014だった。
3,3’-ジクロロベンジジンの塩酸塩(3,3’-ジクロロベンジジン300部に相当する量)と35%塩酸380部を水4000部に加え、0℃に冷却後、40%亜硝酸ソーダ水溶液430部を加え、1時間撹拌する。ここに10%スルファミン酸100部を加え、過剰の亜硝酸ソーダを消失させ、3,3’-ジクロロベンジジンのテトラゾ溶液を得た。これとは別に、水7500部にアセト酢酸-p-トルダイド480部と25%苛性ソーダ水溶液270部を加えて撹拌、溶解させ、次いで10%酢酸1500部を少しずつ加え、カップラー懸濁液とする。続いて、カップラー懸濁液にテトラゾ溶液を2~10℃に保ちながら加え、さらに30分間撹拌後、80℃まで加熱し、30分間撹拌、濾過、水洗して、C.I.ピグメントイエロー55のウェットケーキを得た。このウェットケーキを110℃で一昼夜乾燥させた後、粉砕して、C.I.ピグメントイエロー55からなる比較PY55-1’を得た。比較PY55-1’のイソプロパノール中のゼータ電位は-29.5mV、アゾ顔料に含まれる鉄元素量は124ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.0atomic%、アゾ顔料粒子表面炭素元素濃度Cは73.5atomic%、その比Fe/Cは0.00だった。
3,3’-ジクロロベンジジンの塩酸塩(3,3’-ジクロロベンジジン300部に相当する量)と35%塩酸380部を水4000部に加え、0℃に冷却後、40%亜硝酸ソーダ水溶液430部を加え、1時間撹拌する。ここに10%スルファミン酸100部を加え、過剰の亜硝酸ソーダを消失させ、3,3’-ジクロロベンジジンのテトラゾ溶液を得た。これとは別に、水7500部にアセト酢酸-p-トルダイド480部と25%苛性ソーダ水溶液270部を加えて撹拌、溶解させ、次いで10%酢酸1500部を少しずつ加え、カップラー懸濁液とする。続いて、カップラー懸濁液にテトラゾ溶液を2~10℃に保ちながら加え、さらに30分間撹拌後、80℃まで加熱し、30分間撹拌、濾過、水洗して、C.I.ピグメントイエロー55のウェットケーキを得た。このウェットケーキを水10000部に加え、1時間撹拌する。次いで、硫酸鉄(II)七水和物43.0部を加え、30分間撹拌し、35%過酸化水素1000部を加え、さらに2時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥、粉砕して、C.I.ピグメントイエロー55からなるPY55-1を得た。PY55-1のイソプロパノール中のゼータ電位は-59.2mV、アゾ顔料に含まれる鉄元素量は2410ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.1atomic%、アゾ顔料粒子表面炭素元素濃度Cは72.2atomic%、その比Fe/Cは0.0014だった。
1,2-ビス(2-アミノフェノキシ)-エタン45部と35%塩酸107.7部を水650部に加え、30分間撹拌後、氷を加えて5℃以下に保ちながら、40%亜硝酸ソーダ水溶液67.4部を滴下し、液量を1300部に水で調整してテトラゾ溶液を得た。これとは別に、5-アセトアセチルアミノ-ベンズイミダゾロン93部を水675部に加え、撹拌しながら25%水酸化ナトリウム水溶液119部を加えて溶解させ、液量を900部に水で調整し、カップラー溶液を得た。次に、90%酢酸6部と水1300部を混合し、温度を20℃に保ちながら、20%苛性ソーダ水溶液でpH6.0に調整する。ここに、テトラゾ溶液とカップラー溶液を同時に3時間で滴下した。このとき、反応液温度が20℃、pHが6.0を維持するよう適時氷または5%苛性ソーダ水溶液を添加した。続いて、90℃に加熱し、1時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥し、C.I.ピグメントイエロー180からなる乾燥顔料塊を得た。この乾燥顔料塊60部と、塩化ナトリウム340部、ジエチレングリコール70部を1L双腕型ニーダー(株式会社吉田製作所製)に投入し、80℃で5時間磨砕した。得られた磨砕混練物を、水2000部に加え、60℃に加熱後、1時間撹拌、濾過、水洗して、C.I.ピグメントイエロー180のウェットケーキを得た。このウェットケーキを110℃で一昼夜乾燥させた後、粉砕して、C.I.ピグメントイエロー180からなる比較PY180-1’を得た。比較PY180-1’のイソプロパノール中のゼータ電位は-12.4mV、水中のゼータ電位は-34.9mV、アゾ顔料に含まれる鉄元素量は455ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.0atomic%、アゾ顔料粒子表面炭素元素濃度Cは69.2atomic%、その比Fe/Cは0.00だった。
1,2-ビス(2-アミノフェノキシ)-エタン45部と35%塩酸107.7部を水650部に加え、30分間撹拌後、氷を加えて5℃以下に保ちながら、40%亜硝酸ソーダ水溶液67.4部を滴下し、液量を1300部に水で調整してテトラゾ溶液を得た。これとは別に、5-アセトアセチルアミノ-ベンズイミダゾロン93部を水675部に加え、撹拌しながら25%水酸化ナトリウム水溶液119部を加えて溶解させ、液量を900部に水で調整し、カップラー溶液を得た。次に、90%酢酸6部と水1300部を混合し、温度を20℃に保ちながら、20%苛性ソーダ水溶液でpH6.0に調整する。ここに、テトラゾ溶液とカップラー溶液を同時に3時間で滴下した。このとき、反応液温度が20℃、pHが6.0を維持するよう適時氷または5%苛性ソーダ水溶液を添加した。続いて、90℃に加熱し、1時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥し、C.I.ピグメントイエロー180からなる乾燥顔料塊を得た。この乾燥顔料塊60部と、塩化ナトリウム340部、ジエチレングリコール70部を1L双腕型ニーダー(株式会社吉田製作所製)に投入し、80℃で5時間磨砕した。得られた磨砕混練物を、水2000部に加え、60℃に加熱後、1時間撹拌、濾過、水洗して、C.I.ピグメントイエロー180のウェットケーキを得た。このウェットケーキを水1000部に加え、1時間撹拌する。次いで、35%過酸化水素70部を加え、さらに2時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥、粉砕して、C.I.ピグメントイエロー180からなる比較PY180-2’を得た。比較PY180-2’のイソプロパノール中のゼータ電位は-18.5mV、アゾ顔料に含まれる鉄元素量は434ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.0atomic%、アゾ顔料粒子表面炭素元素濃度Cは68.5atomic%、その比Fe/Cは0.00だった。
1,2-ビス(2-アミノフェノキシ)-エタン45部と35%塩酸107.7部を水650部に加え、30分間撹拌後、氷を加えて5℃以下に保ちながら、40%亜硝酸ソーダ水溶液67.4部を滴下し、液量を1300部に水で調整してテトラゾ溶液を得た。これとは別に、5-アセトアセチルアミノ-ベンズイミダゾロン93部を水675部に加え、撹拌しながら25%水酸化ナトリウム水溶液119部を加えて溶解させ、液量を900部に水で調整し、カップラー溶液を得た。次に、90%酢酸6部と水1300部を混合し、温度を20℃に保ちながら、20%苛性ソーダ水溶液でpH6.0に調整する。ここに、テトラゾ溶液とカップラー溶液を同時に3時間で滴下した。このとき、反応液温度が20℃、pHが6.0を維持するよう適時氷または5%苛性ソーダ水溶液を添加した。続いて、90℃に加熱し、1時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥し、C.I.ピグメントイエロー180からなる乾燥顔料塊を得た。この乾燥顔料塊60部と、塩化ナトリウム340部、ジエチレングリコール70部を1L双腕型ニーダー(株式会社吉田製作所製)に投入し、80℃で5時間磨砕した。得られた磨砕混練物を、水2000部に加え、60℃に加熱後、1時間撹拌、濾過、水洗して、C.I.ピグメントイエロー180のウェットケーキを得た。このウェットケーキを水1000部に加え、1時間撹拌する。次いで、硫酸鉄(II)七水和物2.86部を加え、30分間撹拌し、35%過酸化水素70部を加え、さらに2時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥、粉砕して、C.I.ピグメントイエロー180からなるPY180-1を得た。PY180-1のイソプロパノール中のゼータ電位は-38.8mV、水中のゼータ電位は-36.4mV、アゾ顔料に含まれる鉄元素量は4460ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.1atomic%、アゾ顔料粒子表面炭素元素濃度Cは67.4atomic%、その比Fe/Cは0.0015だった。
C.I.ピグメントレッド213のウェットケーキ(固形分35.0%、東京色材工業株式会社製)71.5部を水429部に加え、60℃に昇温しながら1時間撹拌した。次いで、60℃でさらに2時間30分撹拌した後、濾過、水洗、110℃で一昼夜乾燥、粉砕して、C.I.ピグメントレッド213からなる比較PR213-1’を得た。比較PR213-1’のイソプロパノール中のゼータ電位は27.1mV、アゾ顔料に含まれる鉄元素量は16ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.0atomic%、アゾ顔料粒子表面炭素元素濃度Cは75.1atomic%、その比Fe/Cは0.00だった。
C.I.ピグメントレッド213のウェットケーキ(固形分35.0%、東京色材工業株式会社製)71.5部を水429部に加え、60℃に昇温しながら1時間撹拌した。次いで、硫酸鉄(II)七水和物1.13部を加え、30分間撹拌し、35%過酸化水素35.7部を加え、1時間撹拌した。さらに、硫酸鉄(II)七水和物0.28部を加え、1時間撹拌した後、濾過、水洗、110℃で一昼夜乾燥、粉砕して、C.I.ピグメントレッド213からなるPR213-1を得た。PR213-1のイソプロパノール中のゼータ電位は-38.8mV、アゾ顔料に含まれる鉄元素量は505ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.1atomic%、アゾ顔料粒子表面炭素元素濃度Cは74.3atomic%、その比Fe/Cは0.0013だった。
C.I.ピグメントオレンジ64のウェットケーキ(固形分49.3%、Vijay Chemical Industries製)50.7部を水449部に加え、60℃に昇温しながら1時間撹拌した。次いで、60℃でさらに2時間撹拌した後、濾過、水洗、98℃で一昼夜乾燥、粉砕して、C.I.ピグメントオレンジ64からなる比較PO64-1’を得た。比較PO64-1’のイソプロパノール中のゼータ電位は2.7mV、アゾ顔料に含まれる鉄元素量は20ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.0atomic%、アゾ顔料粒子表面炭素元素濃度Cは59.4atomic%、その比Fe/Cは0.00だった。
C.I.ピグメントオレンジ64のウェットケーキ(固形分49.3%、Vijay Chemical Industries製)50.7部を水449部に加え、次いで硫酸鉄(II)七水和物1.14部を加え、60℃に昇温しながら1時間撹拌した。顔料スラリーに35%過酸化水素35.7部を1時間かけて滴下した後、さらに硫酸鉄(II)七水和物0.29部を加え、1時間撹拌し、濾過、水洗、98℃で一昼夜乾燥、粉砕して、C.I.ピグメントオレンジ64からなるPO64-1を得た。PO64-1のイソプロパノール中のゼータ電位は-41.0mV、アゾ顔料に含まれる鉄元素量は6390ppm、X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Feは0.1atomic%、アゾ顔料粒子表面炭素元素濃度Cは58.1atomic%、その比Fe/Cは0.0017だった。
上記実施例1~11、比較例1~11で得られたアゾ顔料それぞれについて、顔料10g、ポリウレタン樹脂サンプレンIB-501(三洋化成工業株式会社製)20g、酢酸エチル13g、イソプロピルアルコール7g、1/8インチスチールビーズ(持木鋼球軸受株式会社製)180gを250mLポリエチレン製広口瓶に入れ、ペイントシェーカー(株式会社東洋精機製作所製)で30分間分散した。その後、ポリウレタン樹脂サンプレンIB-501 35g、酢酸エチル9.75g、イソプロピルアルコール5.25gを追加で広口瓶に加え、ペイントシェーカー(株式会社東洋精機製作所製)で5分間分散し、ポリウレタンインキをそれぞれ得た。
得られたポリウレタンインキを20℃恒温槽で1時間以上静置し、R85形粘度計RB85L(東機産業株式会社製)で回転速度6rpmでの粘度を測定した。粘度は小さいほど優れる。
得られたポリウレタンインキをPETフィルム ルミラー50T-60(パナック工業株式会社製)にNo.6のバーコーターで展色した。黒色の紙上に、展色フィルムの展色面を下向きに載せ、目視で透明性を判定した。透明性は1~9の9段階で判定し、数字が大きいほど透明性が高く、数字が小さいほど不透明であることを表す。透明性は高いほど優れる。
Claims (6)
- イソプロパノール(IPA)中のゼータ電位が-80mV~-30mVであるアゾ顔料。
- 前記アゾ顔料100質量部あたり金属元素を0.05~2.00質量部含む請求項1に記載のアゾ顔料。
- 前記金属元素が鉄元素である請求項2に記載のアゾ顔料。
- X線光電子分光法によるアゾ顔料粒子表面鉄元素濃度Fe(atomic%)と、アゾ顔料粒子表面炭素元素濃度C(atomic%)の比(Fe/C)が0.20以下である請求項3に記載のアゾ顔料。
- 請求項1~4のいずれか1項に記載のアゾ顔料を含有するインキ。
- 請求項1~4のいずれか1項に記載のアゾ顔料を含有する塗料、プラスチック用着色剤、着色成形品、文具・筆記具用着色剤、捺染剤、トナー、カラーフィルタ用分散液・レジスト、及び化粧料。
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US18/274,904 US20240084155A1 (en) | 2021-02-18 | 2021-12-09 | Azo pigment, ink, paint, colorant for plastics, colored molded article, colorant for stationery and writing materials, printing agent, toner, dispersion and resist for color filters, and cosmetic material |
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WO2019180955A1 (ja) * | 2018-03-23 | 2019-09-26 | 富士電機株式会社 | 電子写真用感光体、その製造方法および電子写真装置 |
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- 2021-12-09 US US18/274,904 patent/US20240084155A1/en active Pending
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JPH06136287A (ja) | 1992-10-22 | 1994-05-17 | Nippon Steel Chem Co Ltd | カラー用カーボンブラック及びその底色制御方法 |
JP2002020673A (ja) * | 2000-04-10 | 2002-01-23 | Seiko Epson Corp | 顔料分散液の製造方法、その方法により得られた顔料分散液、その顔料分散液を用いたインクジェット記録用インク、並びに、そのインクを用いた記録方法および記録物 |
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