WO2009081850A1 - 印刷インキ用顔料組成物、その製造方法、及び印刷インキの製造方法 - Google Patents
印刷インキ用顔料組成物、その製造方法、及び印刷インキの製造方法 Download PDFInfo
- Publication number
- WO2009081850A1 WO2009081850A1 PCT/JP2008/073157 JP2008073157W WO2009081850A1 WO 2009081850 A1 WO2009081850 A1 WO 2009081850A1 JP 2008073157 W JP2008073157 W JP 2008073157W WO 2009081850 A1 WO2009081850 A1 WO 2009081850A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- printing ink
- copper phthalocyanine
- pigment composition
- resin
- calcium carbonate
- Prior art date
Links
- 238000007639 printing Methods 0.000 title claims abstract description 202
- 239000000049 pigment Substances 0.000 title claims abstract description 76
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims abstract description 116
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims abstract description 111
- 229920005989 resin Polymers 0.000 claims abstract description 66
- 239000011347 resin Substances 0.000 claims abstract description 66
- 229910000019 calcium carbonate Inorganic materials 0.000 claims abstract description 56
- 239000002904 solvent Substances 0.000 claims abstract description 39
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- 239000000976 ink Substances 0.000 claims description 229
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- 239000000047 product Substances 0.000 description 23
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
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- KGMSWPSAVZAMKR-UHFFFAOYSA-N Me ester-3, 22-Dihydroxy-29-hopanoic acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(=C(C)C)C=C1CC2 KGMSWPSAVZAMKR-UHFFFAOYSA-N 0.000 description 4
- KGMSWPSAVZAMKR-ONCXSQPRSA-N Neoabietic acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CCC(=C(C)C)C=C2CC1 KGMSWPSAVZAMKR-ONCXSQPRSA-N 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000004945 emulsification Methods 0.000 description 4
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 4
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Images
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-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
Definitions
- the present invention relates to a method for producing a printing ink pigment composition containing a specific extender pigment, a printing ink pigment composition obtained by the production method, and a method for producing printing ink using the same.
- printing ink composition is composed of a synthetic copper phthalocyanine, which is a large needle-shaped stable ( ⁇ -type) crystal particle of several to several hundred microns, which is finely pigmented to an average particle size of about 20 to 300 nm. It is manufactured by uniformly dispersing the product in a varnish for printing ink and a solvent by a kneading and dispersing machine such as a kneader, a roll mill, or a bead mill.
- a solvent salt milling method is widely used in which crude copper phthalocyanine is added with a grinding aid (such as salt) and an organic solvent that promotes crystal transition to a stable type ( ⁇ type) and ground.
- this method requires separation and purification operations of pigmented copper phthalocyanine, a grinding aid, and an organic solvent, and a large amount of wastewater is generated, requiring a great deal of time and labor.
- a method for solving this problem a method has been proposed in which a dry pulverized product of crude copper phthalocyanine is used as a pigment precursor (hereinafter referred to as a pre-pigment) of a raw material for printing ink.
- Patent Document 1 is characterized in that when crude copper phthalocyanine is pulverized by a ball mill, 0.5 to 10% of the resin to be contained in the finished printing ink is added to the pigment amount.
- a method for producing copper phthalocyanine suitable for paste-like printing inks is described, and the use of alkyd resin, hydrocarbon resin, rosin resin modified with maleimide or rosin resin modified with phenol is described as the resin. Has been.
- Patent Document 2 describes that a printing ink resin is added to crude copper phthalocyanine in an amount of 20 to 80% by mass with respect to the copper phthalocyanine and dry pulverized at 80 to 170 ° C., and the resulting pulverized product is used for printing ink.
- a method for producing a printing ink containing stable ( ⁇ -type) crystalline copper phthalocyanine particles having an aspect ratio of 1 to 2 characterized by heating in a solvent or varnish is described.
- Patent Document 3 describes that the resin is contained in an amount of 1 to 200% by mass with respect to crude copper phthalocyanine for the purpose of suppressing acicularization of pigment primary particles and improving the reddish hue and fluidity of the ink.
- a method for producing a printing ink comprising adding a solvent in an amount of 0.5 to 20% by mass to the resin, dry-grinding at 70 to 90 ° C. in a solvent or varnish for printing ink, and processing. has been.
- Patent Document 4 describes a method of using a pre-pigment obtained by adding a resin, a solvent and a specific pigment derivative to crude copper phthalocyanine and dry-grinding at 60 to 180 ° C.
- Patent Document 5 uses a material obtained by dry pulverizing crude copper phthalocyanine and extender pigment and / or printing ink resin that have been surface-treated with a rosin compound in advance. A method for producing a printing ink is described. The treatment amount of the rosin compound is 1 to 50% by mass with respect to the crude copper phthalocyanine, and the use amount of the extender pigment and / or printing ink resin is 1 to 50% by mass with respect to the crude copper phthalocyanine. Has been.
- Patent Document 6 a composition prepared from at least crude copper phthalocyanine, 1 to 100% by mass of extender pigment and 1 to 100% by mass of printing ink resin based on the crude copper phthalocyanine, respectively. A method for producing a printing ink is described.
- a rosin compound which is a raw material for printing ink resins and printing ink resins, is an essential additive substance, and production efficiency due to fixation inside the dry pulverizer and heat storage is increased.
- the problem of quality deterioration of printing ink accompanying reduction, ignition of pulverized material, and deterioration of resin quality remains.
- JP-A-2-294365 Japanese Patent No. 3139396 Japanese Patent No. 3159049 JP 2006-206804 A Japanese Patent No. 3872356 JP 2003-41173 A
- the present invention has been made in view of such circumstances, and is intended to improve the efficiency of the manufacturing process, and at the same time, to provide a printing ink having a high coloring power and a method for manufacturing the same. It is another object of the present invention to provide a printing ink manufacturing method.
- an object of the present invention is to provide a printing ink pigment and a printing ink pigment composition, which do not require the prior surface treatment of crude copper phthalocyanine and do not require the use of a resin, a pigment derivative and a solvent during dry grinding.
- Manufacturing method of printing ink and manufacturing method of printing ink using the pigment composition, and manufacturing of pigment composition for printing ink by dry pulverization of crude copper phthalocyanine using specific calcium carbonate for solving this problem Provided are a printing ink pigment composition for providing a printing ink excellent in various optical properties (coloring power, transparency, gloss, etc.), and a printing ink manufacturing method using the printing ink pigment composition. It is to be.
- the present inventors have prepared a method for producing a pigment composition that can be suitably used for printing ink, a pigment composition obtained by the production method, and a method for producing printing ink using the same.
- a method for producing a pigment composition that can be suitably used for printing ink
- a pigment composition obtained by the production method and a method for producing printing ink using the same.
- a method for producing a pigment composition and further a method for producing a printing ink comprising a step of heating a mixture containing the pigment composition for printing ink, a resin for printing ink and a solvent for printing ink, and a step of dispersing wet kneaded meat
- a method for producing a pigment composition comprising a step of heating a mixture containing the pigment composition for printing ink, a resin for printing ink and a solvent for printing ink, and a step of dispersing wet kneaded meat
- the present invention provides a printing ink pigment composition characterized by dry pulverizing crude copper phthalocyanine and calcium carbonate having an average particle diameter of 20 to 1500 nm in the substantial absence of a printing ink resin.
- a method for manufacturing a product is provided.
- the present invention also provides an aggregate of copper phthalocyanine particles, wherein the copper phthalocyanine particles include two or more crystal forms, the calcium carbonate particles are included inside the aggregate, and substantially the aggregates.
- a printing ink pigment composition in which a printing ink resin is not present inside the assembly.
- the present invention is a method for producing a printing ink using the printing ink pigment composition, the printing ink pigment composition obtained by the method for producing a printing ink pigment composition described above, and a printing ink resin.
- the manufacturing method of printing ink including the process of heating the mixture containing the solvent for printing ink, and the process of carrying out wet kneading dispersion
- the manufacturing method of the pigment composition for printing inks which can provide printing power with high coloring power, glossiness, and transparency, and this pigment composition for printing inks
- the manufacturing method of the printing ink which used the thing can be provided. More specifically, the present invention relates to a printing ink resin and its resin by dry pulverizing crude copper phthalocyanine and calcium carbonate having an average particle diameter of 20 to 1500 nm substantially in the absence of the printing ink resin.
- Copper phthalocyanine is, for example, a method of heating phthalic anhydride or a derivative thereof and a copper compound in urea in the presence of a catalyst such as ammonium molybdate, a method of reacting phthalodinitrile with a copper compound, an o-cyanobenzamide derivative and copper It is a cyclic compound in which four isoindoles obtained by a method of heating a compound, a method of reacting a 1,3-diiminoisoindoline compound and a copper compound in a hydrophilic solvent, and the like bonded with a nitrogen atom.
- crude copper phthalocyanine refers to the above-mentioned crude copper phthalocyanine, preferably phthalic anhydride or a derivative thereof, urea or a derivative thereof, and a metal compound such as a copper compound, or phthalodinitrile.
- a stable ( ⁇ -type) crude copper phthalocyanine obtained by reacting copper compound with a metal compound such as copper compound, and the content of organic impurities other than copper phthalocyanine is reduced to 5% by mass or less, more preferably 3% by mass or less. It points to what was done.
- examples of the phthalic acid derivative include phthalic acid salt, phthalic anhydride, phthalimide, phthalamic acid and salts thereof or esters thereof.
- examples of the metal source include metal copper, cuprous or cupric halides, copper oxide, copper sulfate, copper sulfide, copper hydroxide and the like.
- organic solvents include aromatic hydrocarbons such as alkylbenzene and alkylnaphthalene, alicyclic hydrocarbons such as alkylcyclohexane and decalin, aliphatic hydrocarbons such as decane and dodecane, aromatic nitro compounds such as nitrobenzene and nitrotoluene, and trichlorobenzene. And aromatic halogenated hydrocarbons such as chloronaphthalene.
- the unpurified copper phthalocyanine obtained immediately after the synthesis obtained by the above reaction is a stable ( ⁇ -type) crystal particle having an average particle size of about 5 to 15 ⁇ m.
- this unpurified product is usually reacted as an impurity.
- About 5 to 20% by mass of a low molecular weight organic compound sometimes produced as a by-product, an unreacted copper compound, an inorganic compound derived from a catalyst such as a molybdenum compound used during the reaction, or the like is contained.
- the organic compound includes a phthalimide derivative.
- the obtained copper phthalocyanine unpurified product can be purified by washing with an inorganic acid solution or an inorganic base solution. Washing with an inorganic acid solution or an inorganic base solution can be carried out using an inorganic acid solution or an inorganic base solution alone, but after washing with one washing liquid, washing with the other washing liquid may be carried out sequentially. Good. In the case of sequentially cleaning with two types of cleaning liquids, the order of cleaning liquids to be used is not particularly limited, but it is preferable to perform cleaning with an inorganic base solution after cleaning with an inorganic acid solution. In the washing with the inorganic acid solution, in addition to the unreacted copper compound, impurities such as organic impurities and inorganic impurities derived from a catalyst such as a molybdenum compound used during the reaction can be removed.
- impurities such as organic impurities and inorganic impurities derived from a catalyst such as a molybdenum compound used during the reaction can be removed.
- an inorganic base solution impurities such as phthalimide derivatives are removed, and a crude copper phthalocyanine having a content of organic compounds other than copper phthalocyanine of 5% by mass or less, preferably 3% by mass or less can be obtained.
- the inorganic base used here include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and they are usually used as an aqueous solution of about 1 to 5% by mass.
- an unpurified copper phthalocyanine is added to these inorganic base solutions and stirred at 30 to 90 ° C. for about 0.5 to 5 hours, and then after separation operations such as filtration and centrifugation. The obtained solid is washed with water and dried.
- organic impurities such as phthalimide derivatives contained in copper phthalocyanine unpurified products are alkali-soluble compounds, so when washed by this method, most of the organic impurities are dissolved in the liquid phase.
- the crude copper phthalocyanine in which the content of organic compounds other than copper phthalocyanine is reduced to 5% by mass or less, preferably 3% by mass or less can be obtained.
- unpurified copper phthalocyanine may be washed while introducing water vapor into the inorganic base solution.
- the mixture was stirred at 70 to 100 ° C. for about 0.5 to 5 hours while introducing water vapor into the slurry solution, and then filtered, After the solid-liquid separation operation, the obtained solid is washed with water and dried to obtain crude copper phthalocyanine. Washing with an inorganic base solution while introducing water vapor in this way promotes hydrolysis of organic impurities, so that the organic impurities can be more efficiently dissolved in the liquid phase. Can be reduced.
- alcohol cleaning with alcohol such as methanol, acetone cleaning, or the like may be performed.
- alcohol cleaning or acetone cleaning is performed, organic impurities soluble in alcohol and acetone can be reduced.
- organic impurities and inorganic impurities can be reduced by appropriately combining washing with an inorganic acid solution, alcohol washing, acetone washing, and the like.
- Calcium carbonate used for dry pulverization with the crude copper phthalocyanine of the present invention is characterized by an average particle diameter of 20 to 1500 nm.
- average particle size In order to produce calcium carbonate having an average particle size of less than 20 nm, it is difficult to obtain it by a generally known synthesis or pulverization method.
- the average particle size is larger than 1500 nm, the optical properties (coloring) of the resulting printing ink are obtained. Strength, transparency, gloss, etc.), printing suitability (emulsification, printing durability, etc.) and dry grinding efficiency are reduced.
- the average particle diameter referred to in the present invention is an average primary particle diameter having a long side measured by a transmission electron microscope, and can be measured by a generally known method such as a transmission electron microscope.
- the amount of calcium carbonate added is not particularly limited, but is preferably 3 to 70 parts by mass with respect to 100 parts by mass of crude copper phthalocyanine. If the content of calcium carbonate is less than this range, the obtained printing ink will not be able to develop sufficient aggregation suppression and coloring power of pulverized copper phthalocyanine, and if it is more than this range, the optical properties and printability will deteriorate. Or the freedom of blending the printing ink is lost, which is not preferable.
- the crystal form of calcium carbonate is not particularly limited, but is preferably a calcite type or an aragonite type, and may be an aggregate of these.
- the calcium carbonate used in the present invention can be either synthetic calcium carbonate or heavy calcium carbonate. However, since the aggregation state is low and less energy is required for dry grinding, synthetic calcium carbonate is more preferably used. be able to.
- the form of calcium carbonate is preferably in a dry state with a moisture content of 1.5% or less from the viewpoint of workability, adhesion to the inside of a dry pulverizer, etc., but the powder of crude copper phthalocyanine in mixing with crude copper phthalocyanine As long as the above properties are not impaired, it can be used in the form of water-containing slurry or wet cake.
- Synthetic calcium carbonate is obtained by calcining limestone and chemically synthesized by a carbon dioxide compounding method, a soluble salt reaction method, or the like, and is sometimes called precipitated calcium carbonate or light calcium carbonate.
- colloidal or semi-colloidal calcium carbonate having a fine and uniform cubic shape, spindle shape, needle shape or the like of about 20 nm to 1500 nm can be produced.
- calcium carbonate particles are produced. It is also possible to perform a surface treatment for the purpose of improving the dispersibility of the resin and suppressing aggregation.
- heavy calcium carbonate is generally obtained by dry or wet pulverization and classification of limestone, and the particle shape is indefinite.
- the surface of calcium carbonate is treated with at least one surface treatment agent selected from the group consisting of resin acids, saturated fatty acids, unsaturated fatty acids, alicyclic carboxylic acids, silane coupling agents, and salts thereof. Although it may or may not be, finely and easily dispersed calcium carbonate particles are easily obtained, and the dry grinding efficiency with crude copper phthalocyanine is improved.
- the surface treatment agent examples include at least one surface treatment agent selected from the group consisting of resin acids, saturated fatty acids, unsaturated fatty acids, alicyclic carboxylic acids, silane coupling agents, and salts thereof.
- Examples of the resin acid include abietic acid, neoabietic acid, parastrinic acid, levopimaric acid, dehydroabietic acid, pimaric acid, isopimaric acid, sandaracopimaric acid, comnic acid, anticopal acid, lambertian acid, dihydroagatoic acid and the like. .
- abietic acid, neoabietic acid, dehydroabietic acid, or parastronic acid is preferable.
- abietic acid is preferable, but is not limited thereto.
- the resin acid salt examples include alkali metal salts such as sodium salt and potassium salt of the resin acid exemplified above, and alkaline earth metal salts such as magnesium salt and calcium salt.
- alkali metal salts such as sodium salt and potassium salt of the resin acid exemplified above
- alkaline earth metal salts such as magnesium salt and calcium salt.
- potassium abietate, potassium neoabietic acid, potassium dehydroabietic acid or potassium parastrinate is preferable, and potassium abietic acid is particularly preferable.
- resin acid derivative examples include disproportionated rosin, maleated rosin, polymerized rosin, and rosin ester.
- disproportionated rosin or rosin ester is preferable, but not limited thereto.
- fatty acids include caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, serotic acid, montanic acid, melicic acid, etc. However, it is not limited to these. Among these, palmitic acid, stearic acid, lauric acid or oleic acid is preferable.
- saturated fatty acid salt examples include alkali metal salts such as sodium salts and potassium salts of the saturated fatty acids exemplified above, and alkaline earth metal salts such as magnesium salts and calcium salts.
- alkali metal salts such as sodium salts and potassium salts of the saturated fatty acids exemplified above
- alkaline earth metal salts such as magnesium salts and calcium salts.
- the saturated fatty acid salt sodium palmitate, sodium stearate or sodium laurate is preferred.
- unsaturated fatty acids include unsaturated fatty acids having two double bonds such as oleic acid, palmitoleic acid, erucic acid, caproleic acid, Linderic acid, eicosenoic acid, and two double bonds such as linoleic acid.
- unsaturated fatty acids having 3 double bonds such as fatty acid, hiragonic acid and linolenic acid
- unsaturated fatty acids having 4 double bonds such as arachidonic acid
- unsaturated fatty acids having triple bonds such as talylic acid.
- oleic acid or erucic acid is preferred.
- Examples of the salt of unsaturated fatty acid include alkali metal salts such as sodium salt and potassium salt of unsaturated fatty acid exemplified above, and alkaline earth metal salts such as magnesium salt and calcium salt.
- alkali metal salts such as sodium salt and potassium salt of unsaturated fatty acid exemplified above
- alkaline earth metal salts such as magnesium salt and calcium salt.
- the salt of the unsaturated fatty acid sodium oleate or sodium erucate is preferable.
- Examples of the alicyclic carboxylic acid include naphthenic acid.
- the silane coupling agent is not particularly limited, but a silane coupling agent that has been conventionally blended in inks, paints, rubbers, plastics, and the like can be used.
- vinyltrimethoxysilane vinyl Triethoxysilane, ⁇ -chloropropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropyltrimethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropyl Methyldimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropylmethyldimethoxysilane, ⁇ -methacryloxyxypropyl trimethoxysilane, ⁇ -methacryloxyxypropylmethyldimethoxysilane, ⁇ -mercaptoprop
- These surface treatment agents can be used alone or in combination of two or more.
- resin acid compounds such as abietic acid, neoabietic acid, disproportionated rosin or rosin ester, fatty acid compounds such as palmitic acid, stearic acid, lauric acid or oleic acid, or any combination thereof.
- abietic acid, disproportionated rosin, stearic acid or oleic acid, or any combination thereof is preferred.
- the surface treatment method can be performed by a generally known method.
- the surface-treated calcium carbonate include, but are not limited to, white glaze (product name: manufactured by Shiraishi Kogyo Co., Ltd.), NEOLITE (product name: manufactured by Takehara Chemical Co., Ltd.), and the like.
- crude copper phthalocyanine and the calcium carbonate are pulverized in a dry pulverizer.
- Crude copper phthalocyanine and calcium carbonate may be separately added to the pulverizer and pulverized, or crude copper phthalocyanine and calcium carbonate may be mixed in advance and this mixture may be added to the dry pulverizer and pulverized.
- Dry pulverization can be performed using, for example, impact force, shearing force, collision between pulverized particles, or the like caused by collision between the pulverization media or between the pulverization media and the inner wall of the pulverization apparatus. It may be performed in the absence.
- media various kinds of commonly known materials can be used, and beads and rods of various sizes can be used.
- dry pulverizing apparatus known and commonly used apparatuses such as an attritor, a ball mill, a vibration mill, a hammer mill, a single-axis or multi-axis extruder, and a kneader can be used.
- grinding media such as a Henschel mixer and a jet mill, can also be used.
- the dry pulverization can be performed in the air, but an inert gas such as nitrogen gas or helium gas may be circulated in the dry pulverizer as necessary, and the interior of the apparatus may be performed in a deoxygenated atmosphere.
- an inert gas such as nitrogen gas or helium gas may be circulated in the dry pulverizer as necessary, and the interior of the apparatus may be performed in a deoxygenated atmosphere.
- the method is also effective in terms of safety.
- Crude copper phthalocyanine becomes a mixed crystal type having two or more crystal forms by pulverization. Therefore, in the pulverization of crude copper phthalocyanine, it is preferable to control the unstable ( ⁇ -type) crystal content of the pulverized product.
- the unstable ( ⁇ -type) crystal content is high, the transition efficiency of copper phthalocyanine to a stable ( ⁇ -type) crystal decreases in the subsequent heating step, and the copper phthalocyanine particles grow into needles. This is because problems such as a decrease in physical property values (viscosity, hue, coloring power, etc.) of the printing ink due to facilitation may occur.
- This unstable ( ⁇ -type) crystal content increases with an increase in the pulverization force of dry pulverization, and has a feature that it decreases as the processing temperature increases.
- the unstable ( ⁇ -type) crystal content is in the range of 35 to 70%.
- dry pulverization is usually preferably performed in the range of 65 to 150 ° C.
- the unstable type ( ⁇ -type) crystal content of the pulverized product was sampled at an appropriate amount every pulverization time after the pulverized product passed, and the specific black angle (2 ⁇ ) of the X-ray diffraction pattern of the sample was 6.8 ° ⁇ 0.00. It can be determined by focusing on the ratio (L ⁇ / L ⁇ ) of the peak height (L ⁇ ) of 2 ° and the peak height (L ⁇ ) of 9.2 ° ⁇ 0.2 °.
- Dry pulverization is preferably performed in the presence of crude copper phthalocyanine and calcium carbonate so that the average particle size of the pulverized product is 20 to 300 nm.
- the calcium carbonate particles improve the fine pulverization efficiency of the crude copper phthalocyanine and suppress the strong aggregation of the pulverized pulverized copper phthalocyanine particles.
- a ground product of phthalocyanine can be obtained.
- the calcium carbonate used here is pulverized simultaneously with the crude copper phthalocyanine, it has a high refractive index and a high hiding power, so it can be used even with inexpensive calcium carbonate that directly affects the transparency of the printing ink. There is also an advantage.
- the pulverization time during dry pulverization depends on the pulverization temperature, the equipment used, the particle size of the desired pulverized product, or the target ink characteristics of the final printing ink using the pigment composition comprising the pulverized product after dry pulverization or the pigment composition. It is adjusted accordingly.
- This grinding time is usually about 30 minutes to 12 hours at the above grinding temperature.
- the pulverization time varies depending on the type of pulverizer used. For example, when an attritor is used, a preferable pulverization time is about 45 minutes, and when a ball mill is used, a time of about 12 hours can be mentioned. In general, it is preferable to use an attritor because the pulverization efficiency is high and the pulverization is completed in a short time.
- copper pulverization is performed for the purpose of facilitating the control of the dry pulverization efficiency and the transition from the unstable ( ⁇ -type) crystal to the stable ( ⁇ -type) crystal ( ⁇ / ⁇ -type transition).
- a phthalocyanine pigment derivative and a solvent for printing ink can be used in combination.
- a copper phthalocyanine pigment derivative for example, it has a substituent on one or more of the benzene nuclei of copper phthalocyanine, and examples of the substituent include a halogen atom, a sulfonic acid group, a carboxylic acid group or a metal salt thereof, an ammonium salt, and the like. Examples thereof include salts with cationic surfactants, and various derivatives via a methylene group, a carbonyl group, a sulfonyl group, an imino group, and the like are also used.
- the amount of copper phthalocyanine pigment derivative used is not particularly limited, but is 0.1 to 20 parts per 100 parts by mass of crude copper phthalocyanine.
- This pulverization is carried out by adding a liquid substance that does not substantially impair the liquid substance or that does not impair the characteristics of the powder, usually 0.5 to 20% by mass relative to the crude copper phthalocyanine. It can be carried out.
- dry pulverization substantially in the absence of printing ink resin means that there is no printing ink resin in the system at the time of dry pulverization or an amount that affects the effect of the present invention. It means that the resin for printing ink may be contained up to the point not containing the resin for printing ink, that is, the amount of the resin for printing ink in a range not impairing the effect of the present invention.
- the type of resin for printing ink for example, it is less than 1% by mass, more preferably less than 0.5% by mass, further preferably less than 0.1% by mass, based on copper phthalocyanine. Most preferably, it refers to 0% by mass.
- the pigment composition for printing ink of the present invention obtained by the dry pulverization is an aggregate of copper phthalocyanine particles, (1)
- the copper phthalocyanine particles include two or more crystal forms, (2) containing the calcium carbonate particles inside the aggregate, and (3)
- the printing ink resin is substantially absent inside the aggregate.
- the appearance exists as an aggregate of about several mm in which fine copper phthalocyanine particles (primary particles) are aggregated.
- the aggregate of the copper phthalocyanine particles of the present invention contains the calcium carbonate inside the aggregate, and more specifically, the calcium carbonate particles exist in the gap between the particles of the copper phthalocyanine constituting the aggregate. (FIG. 1). Further, since the dry pulverization is carried out substantially in the absence of the printing ink resin, the printing ink resin is not substantially present inside the aggregate.
- the fact that there is substantially no printing ink resin inside the aggregate means that there is no printing ink resin inside the aggregate, or an amount of the printing ink resin that affects the effect of the present invention. It means that the resin for printing inks may be contained up to the point where it does not contain, that is, the amount of the resin that does not impair the effects of the present invention. More specifically, although it varies depending on the type of resin for printing ink, for example, it is less than 1% by weight, more preferably less than 0.5% by weight, further preferably less than 0.1% by weight, based on copper phthalocyanine. Most preferably, it refers to 0% by mass.
- Calcium carbonate is refined into particles having an average particle size of 15 to 200 nm, preferably 20 to 80 nm by the dry pulverization.
- crude copper phthalocyanine is refined into copper phthalocyanine particles (primary particles) having an average particle size of 15 to 200 nm, preferably 17 to 100 nm, more preferably 20 to 80 nm.
- the copper phthalocyanine particles are composed of, for example, the same or a plurality of crystallites, and the average crystallite diameter is about 15 to 100 nm. In some cases, the particles are formed in an amorphous state.
- the purpose of the main heating step is to transfer the crystal form of the dry pulverized copper phthalocyanine from the ⁇ / ⁇ mixed crystal type to the ⁇ type, which is chemically stable and suitable for printing ink.
- it is preferably carried out at a temperature of 70 to 180 ° C.
- stirring with a disperser or the like is not particularly required, and it can be performed under static heating.
- stirring treatment with a single-axis or multi-axis dispersion stirrer or kneader is preferable.
- these dispersers and kneaders any known and commonly used ones can be used. Examples thereof include single-shaft or multi-shaft stirrers such as dispersers and homomixers, kneaders, single-shaft or multi-screw extruders, and the like. These can also be used in combination.
- the transition time varies depending on the printing ink solvent used, the heating temperature, and the stirring state, the heating process can be completed in about several minutes to 3 hours.
- Copper phthalocyanine is mostly transferred to stable crystals ( ⁇ -type) by the main heating step or a wet kneading dispersion step that can be performed thereafter or simultaneously, but a trace amount of unstable crystals of 1% or less. ( ⁇ type) may exist.
- a printing ink varnish prepared in advance from a printing ink resin and a printing ink solvent, and in some cases a gelling agent, etc. can be used, or a commercially available printing ink varnish can be used. You can also.
- the resin for printing ink contains at least one kind generally used for printing ink, such as rosin modified phenolic resin, rosin modified maleic resin, alkyd resin, petroleum resin modified rosin modified phenolic resin, petroleum resin, preferably rosin It is a modified phenolic resin.
- the rosin-modified phenol resin is mainly composed of a product obtained by reacting a phenol resin obtained by condensation reaction of alkylphenol and formaldehyde and rosin, and further comprising a polyhydric alcohol as a constituent component of the resin. It may be what.
- the printing ink solvent is a high-boiling petroleum solvent, an aliphatic hydrocarbon solvent, a higher alcohol solvent, or a vegetable oil, and has an aromatic component of less than 1% by mass, alone or in combination of two or more. A combined composition may be used.
- Any vegetable oil can be used as long as it is usually used as an ink raw material.
- oils such as soybean oil, linseed oil, tung oil, castor oil, dehydrated castor oil, corn oil, safflower oil, canol oil, synthetic oil (and regenerated oil), and the like. These vegetable oils may be used alone or in combination of two or more.
- Preferred printing ink solvents are naphthenic, paraffinic solvents and soybean oil having an aniline point of 65 ° C. to 100 ° C.
- Solvents for such printing ink include, for example, Nippon Oil Corporation AF Solvent No. 4 (aromatic component content 0.1% by mass), AF Solvent No. 5 (0.2% by mass), AF Solvent No. 6 (0.3% by mass), AF Solvent No. 7 (0.2% by mass), soybean oil (Nisshin Oillio Group, Inc .: soybean salad oil) and the like.
- the mixing ratio of the printing ink resin and the printing ink solvent when preparing the printing ink varnish is appropriately adjusted within the range of 20 to 75% by mass of the resin and 25 to 80% by mass of the solvent. be able to.
- the heating step can be performed in the presence of the above-described pigment derivative or additive.
- additives include gelling agents, pigment dispersants, metal dryers, drying inhibitors, antioxidants, antifriction agents, anti-set-off agents, nonionic surfactants, polyhydric alcohols, and the like. Can do.
- the crude copper phthalocyanine in the paste-like mixture that has been subjected to a transition from a mixed crystal type to a stable type ( ⁇ -type) crystal suitable for printing ink and a wet process with the printing ink varnish in the heating process has an individual particle size. Is adjusted to about 15 to 350 nm, but the particles are in an aggregated and agglomerated state, which is not yet a pigment dispersion state suitable for printing ink.
- This paste-like mixture is wet-kneaded with a three-roll mill, bead mill, single-screw or multi-screw extruder generally used in the production of printing inks so that the kneading degree of dispersion is 5 microns or less. This completes the printing ink.
- This wet kneaded dispersion treatment is preferably treated with a bead mill because the copper phthalocyanine mass concentration in the paste-like mixture can be set high, and a high dispersion force can be obtained by selecting the type and particle size of the media. .
- a kneading and dispersing device such as a short-axis or multi-axis extruder that can be charged with crude copper phthalocyanine, a resin for printing ink, a solvent, a printing ink varnish, an additive, etc. and can be heated and cooled, is used. It is also possible to perform the heat treatment step and the wet kneading dispersion step at the same time, which is an effective means although the cost of the apparatus is increased.
- the printing ink is used so that the pigment concentration required for the printing ink finally used (referred to as final printing ink) is obtained.
- the final printing ink may be prepared in one step using a varnish, a printing ink solvent, a constitution base ink, an additive, and the like.
- the final printing ink varnish, solvent, and additives are used in advance.
- printing ink base ink a mixture having a higher pigment concentration than printing ink
- printing ink varnish a mixture having a higher pigment concentration than printing ink
- printing ink solvent a mixture having a higher pigment concentration than printing ink
- constitution base ink a mixture having a higher pigment concentration than printing ink
- additives etc. It is preferable to prepare a final printing ink.
- the mass ratio of copper phthalocyanine in the base ink for printing ink is preferably 15 to 40% in view of the production efficiency of the heat treatment step and the wet kneading dispersion treatment step.
- the copper phthalocyanine contained in the base ink for printing ink or the final printing ink suppresses the crystal growth of primary particles during crystal change, and forms fine particles with a narrow particle size distribution and a small particle size.
- the reason for this is not clear, but it seems that the calcium carbonate added in the dry pulverization not only acted as a pulverizing aid but also exhibited an effect of suppressing crystal growth.
- the average particle size of copper phthalocyanine (primary particles) contained in the base ink for printing ink or the final printing ink is 15 to 350 nm, and more preferably 20 to 200 nm.
- the presence of giant particles having a particle diameter exceeding 400 nm is suppressed, and for example, a giant particle having a particle diameter exceeding 400 nm can be obtained.
- the copper phthalocyanine is not a needle-like crystal having a large ratio (aspect ratio) of a long side length and a short side length having a crystal form size, but a cubic crystal having a small aspect ratio. Due to these characteristics, a printing ink using the pigment composition for printing ink of the present invention is excellent in various optical properties (coloring power, transparency, gloss, etc.) and printability (emulsification, printing durability, etc.).
- the pigment composition for printing ink of the present invention is applied to various printing inks such as offset printing ink (heat set-off wheel ink, sheet-fed ink, newspaper ink, UV ink, etc.), flexographic printing ink, gravure printing ink, special function ink, etc. However, it can be suitably applied to offset printing inks.
- offset printing ink heat set-off wheel ink, sheet-fed ink, newspaper ink, UV ink, etc.
- flexographic printing ink flexographic printing ink
- gravure printing ink gravure printing ink
- special function ink special function ink
- Example 1 Production of Pigment Composition for Printing Ink-1
- the crude copper phthalocyanine of Production Example 1 and calcium carbonate were blended in the ratio shown in Table 1 so that the target pigment composition for printing ink was 500 g, and an attritor (diameter 3/8 diameter) having an internal volume of 25 liters.
- FIG. 1 is a cross-sectional view of a printing ink pigment composition (aggregate) obtained by dry pulverization, processed with a microtome into thin film sections, and photographed with a transmission electron microscope (TEM). Aggregates of copper phthalocyanine particles It was revealed that calcium carbonate particles (black spots) were present in the (grayish portion of the background).
- Examples 2 to 10 were carried out in the same manner as in Example 1 under the conditions shown in Table 1 to obtain a pigment composition for printing ink.
- Comparative Example 1 Preparation of Pigment Composition for Printing Ink-2 The same as in Example 1 with the combination of the crude copper phthalocyanine obtained in Production Example 1, the rosin-modified resin shown in Table 1 (Beccasite F7310, DIC (former Dainippon Ink and Chemicals)) and calcium carbonate Comparative Examples 1 to 4 were carried out by the operations described above to obtain printing ink pigment compositions shown in Table 1.
- Example 11 Preparation of base ink for printing ink Printing ink pigment composition obtained in Example 1 and printing ink varnish obtained in Production Example 2, AF Solvent No. 7 (manufactured by Nippon Oil Corporation) Soybean oil (Nisshin Oilio Group Co., Ltd.) was uniformly mixed at a blending ratio shown in Table 2 so that the content of copper phthalocyanine was 30% by mass, and then heat-treated at 90 to 120 ° C. for 2 hours.
- bead milling (Buhler K8 type lab bead mill, ⁇ 2 mm zirconia beads, filling rate 90%, rotor rotation speed 950 rpm) is performed at 90 ° C. to 110 ° C.
- a base ink for printing ink was prepared at a temperature.
- Table 3 shows the average particle size, particle size distribution, aspect ratio, and crystal form of copper phthalocyanine (primary particles) contained in the printing ink base inks obtained in Examples 11 to 20 and Comparative Examples 5 to 8.
- Example 7 (manufactured by Nippon Oil Corporation), production
- the constitution base ink obtained in Example 3 was combined as shown in Table 4, and the viscosity at 25 ° C. of the Raleigh viscometer was adjusted to 20 to 25 Pa ⁇ S to prepare a printing ink.
- coloring power (D ratio 12 ) of the printing ink (Comparative Example 12) is taken as a standard and the value is set to 100.
- D actual 21 the coloring power of printing ink
- both mass concentration is 30%.
- White ink Xg is further added to the dark-color printing ink (Example 21) to make the density coincide with that of the printing ink (Comparative Example 12). At this time, the following equation holds.
- the D actual 21 is obtained by the following equation.
- Example 21 In the case of the printing ink (Example 21), 9.5 g of white ink was added to the printing ink (Example 21) and the concentrations were matched, so the coloring power of the printing ink (Example 21) was expressed by the formula (2 ) To 110.
- the printing ink pigment composition containing the specific extender pigment according to the production method of the present invention, and the printing ink using the printing ink pigment composition are the same as the printing ink according to the conventional method. It was confirmed that the product had high coloring power quality.
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Abstract
Description
なお、本発明において実質的に印刷インキ用樹脂の不存在下で、乾式粉砕するとは、乾式粉砕時の系内に印刷インキ用樹脂が全く存在しないか、本発明の効果に影響を与える量の印刷インキ用樹脂を含有しないところまで、すなわち、本発明の効果を損ねない範囲の量の印刷インキ用樹脂を含有していても良いことを意味するものとする。より具体的には、印刷インキ用樹脂の種類にもより異なるが、例えば、銅フタロシアニンに対して1質量%未満、より好ましくは0.5質量%未満、さらに好ましくは0.1質量%未満、最も好ましくは0質量%を指す。
(1)前記銅フタロシアニン粒子が2種以上の結晶形を含み、
(2)前記凝集体内部に前記炭酸カルシウム粒子を含み、かつ、
(3)実質的に、前記凝集体内部に印刷インキ用樹脂が存在しない、ことを特徴とする。
そして、好ましい印刷インキ用溶剤としては、溶剤のアニリン点が65℃~100℃を有するナフテン系、パラフィン系溶剤、大豆油でありこの様な印刷インキ用溶剤としては、例えば、新日本石油(株)製のAFソルベント4号(芳香族成分含有量0.1質量%)、AFソルベント5号(同0.2質量%)、AFソルベント6号(同0.3質量%)、AFソルベント7号(同0.2質量%)、大豆油(日清オイリオグループ株式会社:大豆サラダ油)等が挙げられる。
(銅フタロシアニンの結晶含有比測定)
粉砕物及び試作インキ中の銅フタロシアニンの不安定型(α型)結晶/安定型(β型)結晶の含有比は、(株)リガク製粉末X線回折装置 RINT1100を用いて、X線回折図の特異ブラック角(2θ)が6.8°±0.2°のピーク高さ(Lα)と9.2°±0.2°のピーク高さ(Lβ)の比に着眼して求めた。
(銅フタロシアニンの純度測定)
硫酸法による純度測定により計測した。
(銅フタロシアニン一次粒子の平均粒子径)
被測定物をシクロヘキサン中に質量比で500~5,000倍希釈したものを透過型電子顕微鏡撮影(TEM)用のグリッドに滴下、乾燥させ、撮影した画像中から銅フタロシアニンの一次粒子100個の長径長を実測した平均値である。
(炭酸カルシウムの平均粒子径)
・乾式粉砕に用いる炭酸カルシウム
炭酸カルシウムをシクロヘキサン中に質量比で500~5,000倍希釈したものを透過型電子顕微鏡撮影(TEM)用のグリッドに滴下、乾燥させ、撮影した画像中から粒子100個の長径長を実測した平均値である。
・乾式粉砕後の炭酸カルシウム
乾式粉砕して得られた印刷インキ用顔料組成物(凝集体)をマイクロトームで薄膜切片加工し、透過型電子顕微鏡(TEM)撮影した凝集体断面の画像中から炭酸カルシウムの分散粒子100個の長径長を実測した平均値である。
(試作インキの練肉分散度測定)
鋼の盤に深さが0~0.025mmまで変化している2本の溝を刻んだグラインドメーターの最深部にインキを置き、スクレーバーで浅い方に引き伸ばし、粗粒子の直径より浅いところにできるスジの位置の目盛りから求めた。
*)((社)色材協会編集の色材工学ハンドブックのII-III印刷インキの5.1.2印刷インキ試験方法の(1)に記載の方法による。
(試作インキの着色力評価方法)
着色力の評価は、印刷インキ5gと白インキ(DIC(旧 大日本インキ化学工業)(株)製カルトンセルフ709白)95gとを各々よく混合して練り合わせた着色力確認用インキを作り、この白希釈インキを用いてへら引きにより次に示す手順で着色力を評価する。
(試作インキの光沢評価方法)
実施例1~7、比較例1~5で作製したインキを日本工業規格JIS K 5701-1によって定められた展色方法に則って、0.125mlをアート紙に展色して展色物を得た。この展色物を、Gardner社製反射型光沢計で光沢を測定し、その数値を表示した。
(試作インキの透明性評価方法)
透明性差は(社)色材協会編集の色材工学ハンドブックのII-III印刷インキの5.1.2印刷インキ試験方法の(8)(ii)に記載のへら引きによる方法で測定評価した。透明性が非常に高いものを5、非常に低いものを1とした。
(試作インキの展色濃度評価方法)
0.125ccのインキを計量し、RIテスターにて紙面展色、乾燥後、Gretagmacbeth製分光光度計「SpectroEye」、濃度基準DIN16536で展色物の10カ所を測定、最大値、最小値を除いた平均値をインキの着色力値(展色濃度)とした。
(製造例1)粗製銅フタロシアニンの作製
無水フタル酸1218部、尿素1540部、無水塩化第一銅200部、モリブデン酸アンモニウム5部及び不活性溶媒として、HS-SOL-700(Hwa Sung社製)の混合物4000部を反応器に仕込み、攪拌しながら加熱して200℃まで昇温させた後、同温度で2.5時間反応させた。反応終了後、減圧下で不活性溶媒を留去し、残った反応生成物を2%塩酸(水溶液)8000部中に加え、70℃で1時間攪拌した後、吸引濾過してケーキを得た。引き続き、得られたケーキを2%水酸化ナトリウム水溶液8000部中に加え、70℃で1時間攪拌した後、中和し吸引濾過した。このようにして得られたケーキを80℃の温水で充分洗浄した後、乾燥させて結晶形が安定型(β型)の粗製銅フタロシアニン(純度98%)を作製した。
(実施例1)印刷インキ用顔料組成物の作製-1
製造例1の粗製銅フタロシアニンと炭酸カルシウムを、目的とする印刷インキ用顔料組成物が500gとなるように、表1に示した比率で配合し、内容積25リットルのアトライター(直径3/8インチのスチールボール 67Kgを含む)中に投入して回転数200rpm、内温80~110℃で60分間粉砕して、印刷インキ用顔料組成物を作製した。得られた印刷インキ用顔料組成物中の銅フタロシアニンの一次粒子の平均粒子径と、α形/β型の結晶比率、および銅フタロシアニン粒子が集合してできた凝集体中に含まれる炭酸カルシウム粒子の存在をTEM写真(図1)にて確認し、その平均粒子径を表1に記載した。図1は、乾式粉砕して得られた印刷インキ用顔料組成物(凝集体)をマイクロトームで薄膜切片加工し、透過型電子顕微鏡(TEM)撮影した断面図であり、銅フタロシアニン粒子の凝集体(バックグラウンドの灰色状のもこもこした部分)中に炭酸カルシウム粒子(黒点)が存在することが明かとなった。
(比較例1)印刷インキ用顔料組成物の作製-2
製造例1で得られた粗製銅フタロシアニンと表1に示したロジン変性樹脂(ベッカサイトF7310、DIC(旧 大日本インキ化学工業)(株)製)及び炭酸カルシウムの組み合わせにより、実施例1と同様の操作で比較例1~4を行い、表1に記載の印刷インキ用顔料組成物を得た。
A:銅フタロシアニン、B:樹脂、C:炭酸カルシウム
Cal:カルサイト、Ara:アラゴナイト
合立:合成立方形、重不:重質不定形、合紡:合成紡錘形、合針:合成針状
(製造例2)印刷インキワニスの製造
ロジン変性フェノール樹脂(ベッカサイトF-7310(DIC(旧 大日本インキ化学工業)製))を45部、大豆油を15部、AFソルベント7号(新日本石油(株)製)を39部仕込み、180℃に昇温して、同温度で50分放置した後、ゲル化剤としてアルミキレート(アルミニウム ジイソプロキシド モノエチルアセテート)1部を仕込み、180℃で30分間撹拌して印刷インキ用ワニスを得た。
(実施例11)印刷インキ用ベースインキの作製
上記実施例1で得られた印刷インキ用顔料組成物と製造例2で得られた印刷インキワニス、AFソルベント7号(新日本石油(株)製)、大豆油(日清オイリオグループ(株))を銅フタロシアニンの含有率が30質量%となるような表2に示す配合比率で均一混合した後、90~120℃で2時間加熱処理した。その後、練肉分散度が5ミクロン以下になるようにビーズミル(Buhler(株)K8型ラボビーズミル、φ2mmジルコニアビーズ、充填率90%、ローター回転数950rpm)練肉分散処理を90℃~110℃の温度で行い、印刷インキ用ベースインキを作製した。
炭酸カルシウム(白石カルシウム(株)製 白艶華T-DD)40部と製造例2で得た印刷インキワニス50部、AFソルベント7号(新日本石油(株)製)10部を均一になるまで撹拌混合した後、3本ロールミルで粒度5μm以下になるまで練肉分散処理を行い、体質ベースインキを得た。
(実施例21)印刷インキの作製
上記実施例11で得られた印刷インキ用ベースインキと製造例2で得られた印刷インキ用ワニス、AFソルベント7号(新日本石油(株)製)、製造例3で得られた体質ベースインキを表4に示した組み合わせ、ラレー粘度計25℃における粘度を20~25Pa・Sに撹拌調整し、印刷インキを作製した。
Claims (8)
- 粗製銅フタロシアニンと、平均粒子径が20~1500nmである炭酸カルシウムとを、実質的に印刷インキ用樹脂の不存在下で、乾式粉砕することを特徴とする印刷インキ用顔料組成物の製造方法。
- 粗製銅フタロシアニン100質量部に対して、炭酸カルシウムが3~70質量部である請求項1に記載の印刷インキ用顔料組成物の製造方法。
- 炭酸カルシウムの結晶形が、カルサイト型またはアラゴナイト型である請求項1または2に記載の印刷インキ用顔料組成物の製造方法。
- 炭酸カルシウムが、樹脂酸、飽和脂肪酸、不飽和脂肪酸、脂環族カルボン酸、シランカップリング剤、及びそれらの塩からなる群から選ばれる少なくとも1種の表面処理剤により表面処理されたものである、請求項1乃至3のいずれかに記載の印刷インキ用顔料組成物の製造方法。
- (1)請求項1乃至4のいずれかに記載の印刷インキ用顔料組成物の製造方法により得られる印刷インキ用顔料組成物、印刷インキ用樹脂及び印刷インキ用溶剤を含む混合物を加熱する工程と、
(2)該混合物を湿式練肉する工程と
を含む印刷インキの製造方法。 - 銅フタロシアニン粒子の凝集体であって、(1)前記銅フタロシアニン粒子が2種以上の結晶形を含み、(2)前記凝集体内部に前記炭酸カルシウム粒子を含み、かつ、(3)実質的に前記凝集体内部に印刷インキ用樹脂が存在しない、ことを特徴とする印刷インキ用顔料組成物。
- 前記炭酸カルシウム粒子の平均粒子形が15~200nmである請求項6記載の印刷インキ用顔料組成物。
- 前記銅フタロシアニン粒子の平均粒子径が20~300nmである請求項6記載の印刷インキ用顔料組成物。
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EP08864734.2A EP2253675B1 (en) | 2007-12-21 | 2008-12-19 | Pigment composition for printing ink, method for production thereof, and method for production of printing ink |
CN2008801215588A CN101903470A (zh) | 2007-12-21 | 2008-12-19 | 印刷油墨用颜料组合物、其制造方法以及印刷油墨的制造方法 |
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JP7135616B2 (ja) * | 2018-09-07 | 2022-09-13 | コニカミノルタ株式会社 | 静電荷像現像用トナー |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02294365A (ja) | 1989-04-08 | 1990-12-05 | Basf Ag | ペースト状の高粘度印刷インキに適した銅フタロシアニンの製造方法、およびペースト状印刷インキの製造方法 |
JP3139396B2 (ja) | 1996-02-05 | 2001-02-26 | 東洋インキ製造株式会社 | 印刷インキの製造方法 |
JP3159049B2 (ja) | 1996-04-26 | 2001-04-23 | 東洋インキ製造株式会社 | 顔料組成物の製造方法、顔料組成物およびその用途 |
JP2003041173A (ja) | 2001-07-26 | 2003-02-13 | Dainichiseika Color & Chem Mfg Co Ltd | 印刷インキの製造方法及び印刷インキ |
JP2003049102A (ja) * | 2001-08-07 | 2003-02-21 | Dainichiseika Color & Chem Mfg Co Ltd | 印刷インキの製造方法 |
JP2003073581A (ja) | 2001-08-31 | 2003-03-12 | Dainippon Ink & Chem Inc | 顔料の分散用ベース組成物および分散方法 |
JP2003165925A (ja) * | 2001-11-29 | 2003-06-10 | Nippon Paint Co Ltd | 顔料組成物およびその製法 |
JP2003231829A (ja) * | 2002-02-08 | 2003-08-19 | Dainichiseika Color & Chem Mfg Co Ltd | 印刷インキの製造方法 |
JP2005075919A (ja) * | 2003-08-29 | 2005-03-24 | Toda Kogyo Corp | 水系超微細顔料分散体及び該水系超微細顔料分散体を用いた着色剤 |
JP2006206804A (ja) | 2005-01-31 | 2006-08-10 | Toyo Ink Mfg Co Ltd | 印刷インキ |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2003272923A1 (en) | 2002-10-03 | 2004-04-23 | Maruo Calcium Company Limited | Surface-treated calcium carbonate and resin composition comprising the same |
JP2004287100A (ja) | 2003-03-20 | 2004-10-14 | Fuji Xerox Co Ltd | 両面複写用静電潜像現像用乾式トナー、現像剤および画像形成方法 |
JP4089479B2 (ja) | 2003-03-24 | 2008-05-28 | 富士ゼロックス株式会社 | 画像形成方法 |
JP2005002250A (ja) * | 2003-06-13 | 2005-01-06 | Toyo Ink Mfg Co Ltd | β型銅フタロシアニン顔料の製造方法 |
JP4565040B2 (ja) | 2009-03-27 | 2010-10-20 | 白石工業株式会社 | 表面処理炭酸カルシウム及びそれを含むペースト状樹脂組成物 |
-
2008
- 2008-12-19 CN CN2008801215588A patent/CN101903470A/zh active Pending
- 2008-12-19 WO PCT/JP2008/073157 patent/WO2009081850A1/ja active Application Filing
- 2008-12-19 EP EP08864734.2A patent/EP2253675B1/en active Active
- 2008-12-19 US US12/809,296 patent/US8754148B2/en active Active
- 2008-12-19 JP JP2009547071A patent/JP4535207B2/ja active Active
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02294365A (ja) | 1989-04-08 | 1990-12-05 | Basf Ag | ペースト状の高粘度印刷インキに適した銅フタロシアニンの製造方法、およびペースト状印刷インキの製造方法 |
JP3139396B2 (ja) | 1996-02-05 | 2001-02-26 | 東洋インキ製造株式会社 | 印刷インキの製造方法 |
JP3159049B2 (ja) | 1996-04-26 | 2001-04-23 | 東洋インキ製造株式会社 | 顔料組成物の製造方法、顔料組成物およびその用途 |
JP2003041173A (ja) | 2001-07-26 | 2003-02-13 | Dainichiseika Color & Chem Mfg Co Ltd | 印刷インキの製造方法及び印刷インキ |
JP2003049102A (ja) * | 2001-08-07 | 2003-02-21 | Dainichiseika Color & Chem Mfg Co Ltd | 印刷インキの製造方法 |
JP2003073581A (ja) | 2001-08-31 | 2003-03-12 | Dainippon Ink & Chem Inc | 顔料の分散用ベース組成物および分散方法 |
JP2003165925A (ja) * | 2001-11-29 | 2003-06-10 | Nippon Paint Co Ltd | 顔料組成物およびその製法 |
JP2003231829A (ja) * | 2002-02-08 | 2003-08-19 | Dainichiseika Color & Chem Mfg Co Ltd | 印刷インキの製造方法 |
JP3872356B2 (ja) | 2002-02-08 | 2007-01-24 | 大日精化工業株式会社 | 印刷インキの製造方法 |
JP2005075919A (ja) * | 2003-08-29 | 2005-03-24 | Toda Kogyo Corp | 水系超微細顔料分散体及び該水系超微細顔料分散体を用いた着色剤 |
JP2006206804A (ja) | 2005-01-31 | 2006-08-10 | Toyo Ink Mfg Co Ltd | 印刷インキ |
Non-Patent Citations (2)
Title |
---|
"Ganryo no Jiten", ASAKURA SHOTEN, 25 September 2000 (2000-09-25), pages 172 - 174, XP008140798 * |
See also references of EP2253675A4 |
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WO2011145187A1 (ja) * | 2010-05-19 | 2011-11-24 | 荒川化学工業株式会社 | ロジン変性フェノール樹脂、その製造方法、印刷インキ用ワニス、および印刷インキ |
EP2573123A1 (en) * | 2010-05-19 | 2013-03-27 | Arakawa Chemical Industries, Ltd. | Rosin-modified phenol resin, process for production thereof, varnish for printing ink, and printing ink |
EP2573123A4 (en) * | 2010-05-19 | 2014-01-22 | Arakawa Chem Ind | COLOPHONIUM MODIFIED PHENOL RESIN, METHOD OF MANUFACTURING THEREOF, LACQUER FOR PRINTING INK AND PRINTING INK |
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EP2253675A1 (en) | 2010-11-24 |
CN101903470A (zh) | 2010-12-01 |
JP4535207B2 (ja) | 2010-09-01 |
EP2253675B1 (en) | 2018-07-04 |
JPWO2009081850A1 (ja) | 2011-05-06 |
US8754148B2 (en) | 2014-06-17 |
US20100331460A1 (en) | 2010-12-30 |
EP2253675A4 (en) | 2013-06-05 |
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