JPH064775B2 - Method for producing phthalocyanine green pigment - Google Patents
Method for producing phthalocyanine green pigmentInfo
- Publication number
- JPH064775B2 JPH064775B2 JP24550086A JP24550086A JPH064775B2 JP H064775 B2 JPH064775 B2 JP H064775B2 JP 24550086 A JP24550086 A JP 24550086A JP 24550086 A JP24550086 A JP 24550086A JP H064775 B2 JPH064775 B2 JP H064775B2
- Authority
- JP
- Japan
- Prior art keywords
- phthalocyanine green
- pigment
- parts
- crude
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims description 43
- 239000001056 green pigment Substances 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000002904 solvent Substances 0.000 claims description 21
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- 230000002140 halogenating effect Effects 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 5
- 238000000227 grinding Methods 0.000 claims description 5
- 238000001238 wet grinding Methods 0.000 claims description 5
- 239000000374 eutectic mixture Substances 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 239000000049 pigment Substances 0.000 description 30
- 238000000034 method Methods 0.000 description 28
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 239000000976 ink Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 229910017053 inorganic salt Inorganic materials 0.000 description 3
- 230000000485 pigmenting effect Effects 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000010532 solid phase synthesis reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 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 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
- Developing Agents For Electrophotography (AREA)
Description
【発明の詳細な説明】 「発明の目的」 （産業上の利用分野） 本発明は，フタロシアニングリーン顔料の製造法に関
し，さらには高い着色力を有するフタロシアニングリー
ン顔料の製造法である。DETAILED DESCRIPTION OF THE INVENTION "Object of the Invention" (Field of Industrial Application) The present invention relates to a method for producing a phthalocyanine green pigment, and further to a method for producing a phthalocyanine green pigment having high tinting strength.
（従来の技術） フタロシアニングリーン顔料は，塗料，印刷インキ，樹
脂の着色剤等として使用されている。このフタロシアニ
ン顔料の合成方法としては，クロロベンゼン中でハロゲ
ン化するクロロベンゼン法，溶融無水フタル酸中でハロ
ゲン化する無水フタル酸法，無水塩化アルミニウムおよ
び塩化ナトリウムの共融混合物中でハロゲン化する無水
塩化アルミニウム法，クロロスルホン酸中でハロゲン化
するクロロスルホン酸法，溶剤中でテトラクロロフタル
酸から合成する方法，無機塩中で塩素ガスにより塩素化
する固相法などが知られている。(Prior Art) Phthalocyanine green pigments are used as paints, printing inks, colorants for resins, and the like. The phthalocyanine pigment can be synthesized by the chlorobenzene method for halogenating in chlorobenzene, the phthalic anhydride method for halogenating in molten phthalic anhydride, or the anhydrous aluminum chloride for halogenating in a eutectic mixture of anhydrous aluminum chloride and sodium chloride. Methods, chlorosulfonic acid method of halogenating in chlorosulfonic acid, method of synthesizing from tetrachlorophthalic acid in solvent, solid phase method of chlorinating with chlorine gas in inorganic salt are known.
粗製フタロシアニングリーンは，色相が不鮮明で着色力
がないため，顔料化する必要がある。この顔料化方法と
しては，湿式磨砕，硫酸法または結晶化溶剤法が知られ
ている。Crude phthalocyanine green needs to be pigmented because its hue is unclear and has no tinting strength. Wet grinding, a sulfuric acid method, or a crystallization solvent method is known as a pigmenting method.
湿式磨砕法は，食塩，芒硝などの無機塩およびジエチレ
ングリコール，ポリエチレングリコールなどの湿潤剤，
すなわち粉砕助剤を使用し，ニーダー，バンバリーミキ
サーなどで磨砕処理した後，粉砕助剤を除去して顔料を
得る方法であるが，フタロシアニングリーンの場合，得
られた顔料は低い着色力を示し，良好な方法とは言い難
いのが現状である。The wet milling method uses inorganic salts such as salt and sodium sulfate, and wetting agents such as diethylene glycol and polyethylene glycol,
In other words, this is a method in which a grinding aid is used and subjected to grinding treatment with a kneader or a Banbury mixer, and then the grinding aid is removed to obtain a pigment. In the case of phthalocyanine green, the obtained pigment shows low tinting strength. At present, it is difficult to say that this is a good method.
硫酸法は，粗製フタロシアニングリーンを硫酸に溶解
または懸濁させた後，水中に流入させることにより，再
結晶化して，顔料を得る方法であるが，これもまた，得
られた顔料は低い着色力しか示さない。The sulfuric acid method is a method in which crude phthalocyanine green is dissolved or suspended in sulfuric acid and then poured into water to recrystallize to obtain a pigment, but the pigment obtained also has a low tinting strength. Only show.
結晶化溶剤法は，粗製フタロシアニングリーンにクロロ
ベンゼン，ニトロベンゼン，トルエン，オルソクロロト
ルエン，キシレンなどの結晶化溶剤または該溶剤のエマ
ルジョンで処理した後，結晶化溶剤を煮沸，蒸溜等によ
り除去して顔料を得る方法である。この結晶化溶剤法に
より得られたフタロシアニングリーン顔料は，比較的高
い着色力を示すが，まだ十分とは言い難い。In the crystallization solvent method, crude phthalocyanine green is treated with a crystallization solvent such as chlorobenzene, nitrobenzene, toluene, orthochlorotoluene, xylene or an emulsion of the solvent, and then the crystallization solvent is removed by boiling, distilling or the like to remove the pigment. Is the way to get. The phthalocyanine green pigment obtained by this crystallization solvent method shows a relatively high tinting strength, but it is still not sufficient.
（発明が解決しようとする問題点） このような点から本発明は，粗製フタロシアニングリー
ンの顔料化法に関し，高い着色力を示す顔料が得られる
方法を提供するものである。(Problems to be Solved by the Invention) From such a point of view, the present invention relates to a method for pigmenting crude phthalocyanine green, and provides a method for obtaining a pigment having high tinting strength.
「発明の構成」 （問題点を解決するための手段） 本発明は，粗製フタロシアニングリーンを，結晶化溶剤
または該溶剤のエマルジョンで処理した後，粉砕助剤を
使用して湿式磨枠してなるフタロシアニングリーン顔料
の製造法である。さらには，フタロシアニンを，無水塩
化アルミニウムおよび塩化ナトリウムの共融混合物中で
ハロゲン化してなる粗製フタロシアニングリーンを使用
するフタロシアニングリーン顔料の製造法である。[Structure of the Invention] (Means for Solving Problems) The present invention comprises treating crude phthalocyanine green with a crystallization solvent or an emulsion of the solvent, and then subjecting it to wet polishing using a grinding aid. This is a method for producing a phthalocyanine green pigment. Further, it is a method for producing a phthalocyanine green pigment using crude phthalocyanine green obtained by halogenating phthalocyanine in a eutectic mixture of anhydrous aluminum chloride and sodium chloride.
本発明は，粗製フタロシアニングリーンの顔料化法とし
て，結晶化溶剤法および湿式磨枠法を組み合せることに
より，極めて着色力の優れた顔料が得られることを見出
したものである。The present invention has found that as a method for pigmenting crude phthalocyanine green, a pigment having an extremely excellent tinting strength can be obtained by combining a crystallization solvent method and a wet polishing method.
粗製フタロシアニングリーンの製法としては，従来より
行われている方法がそのまま適用できる。例えば無水塩
化アルミニウム法は，無水塩化アルミニウムと食塩との
共融混合物中にフタロシアニンを溶解させ，１５０〜２
００℃で，塩素，臭素などのハロゲンを導入し，フタロ
シアニン１原子当り，ハロゲン原子を１４〜１６子にし
た後，該混合物を水に投入し，ロ過，水洗して粗製フタ
ロシアニングリーンを得る法である。その他にクロロス
ルホン酸法，固相法，その他の方法で合成された粗製フ
タロシアニングリーンであってもよい。As a method for producing the crude phthalocyanine green, the conventional method can be applied as it is. For example, in the anhydrous aluminum chloride method, phthalocyanine is dissolved in a eutectic mixture of anhydrous aluminum chloride and sodium chloride,
A method of obtaining a crude phthalocyanine green by introducing halogen such as chlorine and bromine at 00 ° C to make 14 to 16 halogen atoms per atom of phthalocyanine, and then pouring the mixture into water and filtering and washing with water. Is. Alternatively, it may be crude phthalocyanine green synthesized by the chlorosulfonic acid method, the solid phase method, or another method.
本発明では，粗製フタロシアニングリーンの精製物を，
結晶化溶剤で処理する。この結晶化溶剤法は，粗製フタ
ロシアニングリーンウェットケーキを水中に投入して，
スラリーにし，つぎに水酸化ナトリウムを投入し，ｐＨ
を７以上に，好ましくは９〜１３に調製し，クロロベン
ゼン，ニトロベンゼン，トルエン，オルソクロロトルエ
ンキシレンなどの結晶化溶剤または該溶剤の水系エマル
ジョンを，粗製フタロシアニングリーン１００重量部に
対し溶剤分で１０〜２０重量部投入する。さらに，系を
加熱し，撹拌した後，ロ過，水洗，乾燥する方法であ
る。In the present invention, a purified product of crude phthalocyanine green is
Treat with crystallization solvent. In this crystallization solvent method, the crude phthalocyanine green wet cake is put into water,
Slurry, then add sodium hydroxide, pH
Is adjusted to 7 or more, preferably 9 to 13, and a crystallization solvent such as chlorobenzene, nitrobenzene, toluene, orthochlorotoluene xylene or an aqueous emulsion of the solvent is added in an amount of 10 to 10 parts by weight with respect to 100 parts by weight of crude phthalocyanine green. Add 20 parts by weight. Furthermore, the system is heated, stirred, filtered, washed with water, and dried.
結晶化溶剤法で処理されたフタロシアニングリーンは，
次に湿式磨砕される。湿式磨砕は，結晶化溶剤法で処理
されたフタロシアニングリーン１００重量部，食塩など
の無機塩１００〜１０００重量部，ジエチレグリコール
などの湿潤剤３０〜３００重量部をニーダーなどで混合
し，この混合物を加熱下，磨砕処理した後，水または希
酸水溶液に投入し，無機塩，湿潤剤を溶解し，ロ過，水
洗してウエツトケーキ顔料を得るか，さらに乾燥してド
ライパウダー顔料を得るものである。Phthalocyanine green treated by crystallization solvent method,
Then wet milled. In the wet grinding, 100 parts by weight of phthalocyanine green treated by the crystallization solvent method, 100 to 1000 parts by weight of an inorganic salt such as salt, and 30 to 300 parts by weight of a wetting agent such as diethyl glycol are mixed with a kneader or the like. The mixture is ground under heating and then poured into water or a dilute aqueous acid solution to dissolve the inorganic salt and wetting agent, filtered and washed to obtain a wet cake pigment, or further dried to obtain a dry powder pigment. It is a thing.
本発明で製造された顔料は，塗料，印刷インキ，樹脂の
着色剤などの色材として使用すると，高い着色力を有す
る。特に，ドライパウダー顔料で印刷インキなどを製造
した場合，優れた着色力を示す。The pigment produced according to the present invention has a high tinting strength when used as a coloring material such as a paint, a printing ink, and a colorant for a resin. In particular, when printing inks, etc. are manufactured with dry powder pigments, they show excellent coloring power.
次に本発明を実施例により説明する。例中「部」，
「％」とは，重量部，重量％をそれぞれ示す。Next, the present invention will be described with reference to examples. "Part" in the example,
"%" Indicates parts by weight and% by weight, respectively.
実施例１ 水中に無水塩化アルミニウム法で得られた粗製フタロシ
アニングリーンウェットケーキ（顔料分４０％）２５０
部を投入し，粗製フタロシアニングリーン７％のスラリ
ーを作った。つぎに撹拌下，水酸化ナトリウムを投入
し，スラリーのｐＨを１１〜11.に調製した。そしてキ
シレン１３部，ノニオン系界面活性剤（ノナール３１
０，東邦化学工業製））０．８部，水１５部の組成のエ
マルジョンを投入し，加熱し，８０〜９０℃で１時間撹
拌した後，ロ過，水洗，乾燥してフタロシアニングリー
ンを得た。このフタロシアニングリーン１００部と食塩
２００部，ジエチレングリコール６０部をニーダー中で
混合し，１１０〜１２０℃で６時間磨砕した後，この混
合物を０．５％の硫酸水溶液に投入し，８０〜９０℃で
１時間撹拌し，ロ過，水洗，乾燥してフタロシアニング
リーン顔料を得た。Example 1 Crude phthalocyanine green wet cake (pigment content 40%) 250 obtained by the anhydrous aluminum chloride method in water
Parts to make a slurry of crude phthalocyanine green 7%. Next, sodium hydroxide was added under stirring to adjust the pH of the slurry to 11-11. And 13 parts of xylene, nonionic surfactant (Nonal 31
0, manufactured by Toho Kagaku Kogyo Co., Ltd.)) An emulsion having a composition of 0.8 parts and 15 parts of water was charged, heated, stirred at 80 to 90 ° C. for 1 hour, filtered, washed with water and dried to obtain phthalocyanine green. It was 100 parts of this phthalocyanine green, 200 parts of salt, and 60 parts of diethylene glycol were mixed in a kneader and ground for 6 hours at 110 to 120 ° C., then, this mixture was poured into a 0.5% sulfuric acid aqueous solution to 80 to 90 ° C. The mixture was stirred for 1 hour, filtered, washed with water and dried to obtain a phthalocyanine green pigment.
比較例１ 組成フタロシアニングリーン１００部，食塩２００部，
ジエチレングリコール６０部をニーダー中で混合し，１
１０〜１２０℃で６時間磨砕した後，この混合物を０．
５％の硫酸水溶液に投入し，８０〜９０℃で１時間撹拌
し，ロ過，水洗，乾燥してフタロシアニングリーン顔料
を得た。Comparative Example 1 Composition phthalocyanine green 100 parts, salt 200 parts,
Mix 60 parts of diethylene glycol in a kneader,
After milling at 10-120 ° C. for 6 hours, the mixture was brought to 0.
It was put into a 5% aqueous solution of sulfuric acid, stirred at 80 to 90 ° C. for 1 hour, filtered, washed with water and dried to obtain a phthalocyanine green pigment.
実施例１および比較例１で 得られた顔料を，ロジン変
性フェノール樹脂ワニス中に３本ロールミルで分散し，
オフセットインキを製造した。The pigments obtained in Example 1 and Comparative Example 1 were dispersed in a rosin-modified phenolic resin varnish with a three-roll mill,
An offset ink was produced.
実施例１および比較例１のオフセットインキを試験し，
測色機―カラーマシン（日本電色工業製）により，顔料
の着色力を比較したところ，比較例１の顔料を１００％
とした場合，実施例１では１２０％であった。The offset inks of Example 1 and Comparative Example 1 were tested,
When the tinting strength of the pigments was compared with a colorimeter-color machine (manufactured by Nippon Denshoku Kogyo), 100% of the pigment of Comparative Example 1
When it was set, it was 120% in Example 1.
また，実施例１および比較例１の顔料を，それぞれライ
ムロジン系ワニスにボールミルで分散させ，グラビアイ
ンキを製造した，実施例１の顔料は，比較例１の顔料に
比べ，着色力が１５％程度向上していた。Further, the pigments of Example 1 and Comparative Example 1 were dispersed in a lime rosin-based varnish with a ball mill to produce a gravure ink. The pigment of Example 1 has a tinting strength of about 15% as compared with the pigment of Comparative Example 1. It was improving.
比較例 ２ 粗製フタロシアニングリーン１００部を９６％硫酸１２
００部に投入し，１５〜２０℃で４時間撹拌した後，４
０００部の水に流入させ，８０℃で１時間かくはんし，
ロ過，水洗，乾燥して顔料を得た。Comparative Example 2 100 parts of crude phthalocyanine green was mixed with 96% sulfuric acid 12
It was added to 00 parts and stirred at 15 to 20 ° C. for 4 hours, and then 4
Pour into 000 parts of water and stir at 80 ° C for 1 hour,
The pigment was obtained by filtration, washing with water and drying.
この顔料を実施例１と同様にオフセットインキを製造し
たところ，比較例１とほぼ同じ着色力を示した。When an offset ink was produced from this pigment in the same manner as in Example 1, it showed almost the same tinting strength as in Comparative Example 1.
比較例３ 粗製フタロシアニングリーンウェットケーキ（顔料分４
０％）２５０部にキシレン１５０部，アニオン系界面活
性剤（綜研化学製オレイン酸）４部，水酸化ナトリウム
８部を投入し，混合した後，加熱し，６時間沸点に保っ
た。次に水蒸気蒸溜によりキシレンを除去した後，ロ
過，水洗，乾燥して顔料を得た。Comparative Example 3 Crude phthalocyanine green wet cake (pigment content 4
(0%) 250 parts of xylene, 150 parts of xylene, 4 parts of anionic surfactant (oleic acid manufactured by Soken Chemical Industry Co., Ltd.) and 8 parts of sodium hydroxide were added and mixed, and then heated and kept at the boiling point for 6 hours. Then, xylene was removed by steam distillation, and then filtered, washed with water and dried to obtain a pigment.
この顔料を実施例１と同様にオフセットインキを製造し
たところ，１１０％の着色力を示した。When an offset ink was produced from this pigment in the same manner as in Example 1, it showed a coloring power of 110%.
実施例２ 実施例１のキシレン１３部の代りにトルエン２０部を用
いた以外は，実施例１と同様に溶剤処理し，湿式磨砕処
理して顔料を得た。Example 2 A pigment was obtained by solvent treatment and wet milling in the same manner as in Example 1 except that 20 parts of toluene was used instead of 13 parts of xylene of Example 1.
この顔料の着色力は，実施例１と同様，１２０％であつ
た。The tinting strength of this pigment was 120% as in Example 1.
実施例３ 実施例１の同様に，溶剤処理したフタロシアニングリー
ン１００部，食塩４００部，ジエチレングリコール１０
０部をニーダー中で混合し，１１０〜１２０℃で４時間
磨砕した後，実施例１と同様に処理して顔料を得た。Example 3 As in Example 1, 100 parts of solvent-treated phthalocyanine green, 400 parts of salt, diethylene glycol 10
0 part was mixed in a kneader, ground for 4 hours at 110 to 120 ° C., and treated in the same manner as in Example 1 to obtain a pigment.
この顔料の着色力は，比較例１と比べ，１２０％であっ
た。The tinting strength of this pigment was 120% as compared with Comparative Example 1.
実施例４ 実施例１のキシレン１３部の代りにキシレン２０部を用
いた以外は，実施例１と同様に溶剤処理したフタロシア
ニングリーン１００部，食塩４００部，ジエチレングリ
コール１００部をニーダー中で混合し，１１０〜１２０
℃で３時間磨砕した後，実施例１と同様に処理して顔料
を得た。Example 4 100 parts of solvent-treated phthalocyanine green, 400 parts of salt and 100 parts of diethylene glycol were mixed in a kneader in the same manner as in Example 1 except that 20 parts of xylene was used instead of 13 parts of xylene of Example 1. 110-120
After trituration at C for 3 hours, the same treatment as in Example 1 was carried out to obtain a pigment.
この顔料の着色力は，比較例１と比べ，１２０％であっ
た。The tinting strength of this pigment was 120% as compared with Comparative Example 1.
Claims (2)
剤または該溶剤のエマルジョンで処理した後，粉砕助剤
を使用して湿式磨砕してなることを特徴とするフタロシ
アニングリーン顔料の製造法。1. A method for producing a phthalocyanine green pigment, which comprises treating crude phthalocyanine green with a crystallization solvent or an emulsion of the solvent and then wet-milling the mixture with a grinding aid.
よび塩化ナトリウムの共融混合物中でハロゲン化してな
る粗製フタロシアニングリーンを用いる特許請求の範囲
第１項記載のフタロシアニングリーン顔料の製造法。2. A method for producing a phthalocyanine green pigment according to claim 1, wherein crude phthalocyanine green obtained by halogenating phthalocyanine in a eutectic mixture of anhydrous aluminum chloride and sodium chloride is used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24550086A JPH064775B2 (en) | 1986-10-17 | 1986-10-17 | Method for producing phthalocyanine green pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24550086A JPH064775B2 (en) | 1986-10-17 | 1986-10-17 | Method for producing phthalocyanine green pigment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63101459A JPS63101459A (en) | 1988-05-06 |
| JPH064775B2 true JPH064775B2 (en) | 1994-01-19 |
Family
ID=17134591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24550086A Expired - Lifetime JPH064775B2 (en) | 1986-10-17 | 1986-10-17 | Method for producing phthalocyanine green pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH064775B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0695596A (en) * | 1992-07-29 | 1994-04-08 | Abisare:Kk | Electrostatic notice device |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7019121B2 (en) * | 2003-12-31 | 2006-03-28 | Sun Chemical Corporation | Process for conditioning azo pigments |
| JP2007332302A (en) * | 2006-06-16 | 2007-12-27 | Dainippon Ink & Chem Inc | Method for producing chlorinated metal phthalocyanine pigment |
| JP5233161B2 (en) * | 2007-05-16 | 2013-07-10 | 東洋インキＳｃホールディングス株式会社 | Fine polyhalogenated phthalocyanine pigment, method for producing the same, and coloring composition using the same |
-
1986
- 1986-10-17 JP JP24550086A patent/JPH064775B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0695596A (en) * | 1992-07-29 | 1994-04-08 | Abisare:Kk | Electrostatic notice device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63101459A (en) | 1988-05-06 |
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