JPS63101459A - Production of phthalocyanine green pigment - Google Patents
Production of phthalocyanine green pigmentInfo
- Publication number
- JPS63101459A JPS63101459A JP24550086A JP24550086A JPS63101459A JP S63101459 A JPS63101459 A JP S63101459A JP 24550086 A JP24550086 A JP 24550086A JP 24550086 A JP24550086 A JP 24550086A JP S63101459 A JPS63101459 A JP S63101459A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- phthalocyanine green
- water
- parts
- 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.)
- Granted
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 abstract description 47
- 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 abstract description 24
- 238000002425 crystallisation Methods 0.000 claims abstract description 15
- 230000008025 crystallization Effects 0.000 claims abstract description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 11
- 239000011780 sodium chloride Substances 0.000 claims abstract description 8
- 238000001238 wet grinding Methods 0.000 claims abstract description 8
- 239000000839 emulsion Substances 0.000 claims abstract description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
- 238000000227 grinding Methods 0.000 claims description 6
- 239000000374 eutectic mixture Substances 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 239000000049 pigment Substances 0.000 abstract description 39
- 238000000034 method Methods 0.000 abstract description 33
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000203 mixture Substances 0.000 abstract description 11
- 235000002639 sodium chloride Nutrition 0.000 abstract description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002002 slurry Substances 0.000 abstract description 5
- 238000001914 filtration Methods 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 4
- 239000000080 wetting agent Substances 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- -1 common salt Chemical class 0.000 abstract 1
- 238000004040 coloring Methods 0.000 description 13
- 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 8
- 239000000976 ink Substances 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- 230000026030 halogenation Effects 0.000 description 4
- 238000005658 halogenation reaction Methods 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
- 229910017053 inorganic salt Inorganic materials 0.000 description 3
- 238000005406 washing Methods 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
- 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
- 238000001035 drying Methods 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000003973 paint Substances 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
- 239000000243 solution Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 238000005660 chlorination reaction Methods 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
- 238000004821 distillation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000013305 food Nutrition 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
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000010446 mirabilite Substances 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 230000002747 voluntary effect Effects 0.000 description 1
Abstract
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 OBJECTS OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for producing a phthalocyanine green pigment, and more particularly to a method for producing a phthalocyanine green pigment having high tinting power.
（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。(Prior Art) Phthalocyanine green pigments are used as coloring agents for paints, printing inks, resins, and the like. Methods for synthesizing this phthalocyanine pigment include the chlorobenzene method in which halogenation is carried out in chlorobenzene, the phthalic anhydride method in which halogenation is carried out in molten phthalic anhydride, and the anhydrous aluminum chloride method in which halogenation is carried out in a eutectic mixture of anhydrous aluminum chloride and sodium chloride. Law.
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。Chlorosulfonic acid method of halogenation in chlorosulfonic acid, method of synthesis from tetrachlorophthalic acid in a solvent,
A solid-phase method in which chlorination is performed using chlorine gas in an inorganic salt is known.
粗製フタロシアニングリーンは２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 has two indistinct hues and lacks coloring power, so it needs to be converted into a pigment. Wet milling, a sulfuric acid method, and a crystallization solvent method are known as methods for forming pigments.
湿式磨砕法は２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−。The wet grinding method uses inorganic salts such as di-salt and mirabilite, and wetting agents such as diethylene glycol and polyethylene glycol.
That is, using a grinding aid and kneading.
バンバリーミキサ−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。This method involves grinding with a Banbury mixer and then removing the grinding aid to obtain the pigment, but in the case of phthalocyanine green, the resulting pigment shows low coloring power, so it cannot be called a good method. is the current situation.
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、蒸留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。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 it to obtain a pigment, but the resulting pigment also has low coloring power. In the crystallization solvent method, which is only described, 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, distillation, etc. This is a method to obtain pigments. The phthalocyanine green pigment obtained by this crystallization solvent method exhibits relatively high coloring power, but
It's still far from enough.
（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) In view of the above, the present invention relates to a method for converting crude phthalocyanine green into a pigment, and provides a method by which a pigment exhibiting high coloring power can be obtained.
「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。"Structure of the Invention" (Means for Solving the Problems) The present invention provides a method for treating crude phthalocyanine green with a crystallization solvent or an emulsion of the solvent.
粉砕助剤を使用して湿式磨砕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。This is a method for producing phthalocyanine green pigment by wet grinding using a grinding aid. Furthermore, 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砕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 is based on the discovery that a pigment with extremely excellent tinting power can be obtained by combining a crystallization solvent method and a wet grinding method as a method for converting crude phthalocyanine green into a pigment.
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通用できる。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個にし
た後、該混合物を水に投入し２口過、水洗して粗製フタ
ロシアニングリーンを得る方法である。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 crude phthalocyanine green, conventional methods can be used as they are. For example, in the anhydrous aluminum chloride method, phthalocyanine is dissolved in a eutectic mixture of anhydrous aluminum chloride and common salt.
A method of obtaining crude phthalocyanine green by introducing a halogen such as chlorine or bromine at 00°C to make the number of halogen atoms 14 to 16 per 1 atom of phthalocyanine, and then pouring the mixture into water, passing through 2 mouths, and washing with water. It is. In addition, crude phthalocyanine green synthesized by a chlorosulfonic acid method, a solid phase method, or other methods may be used.
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１１製り、 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、攪拌した後２口過、水洗、乾燥する方法
である。In the present invention, a purified product of crude phthalocyanine green,
Treat with crystallization solvent. This crystallization solvent method involves putting crude phthalocyanine green wet cake into water.
Make a slurry, then add sodium hydroxide to adjust the pH.
to 7 or more, preferably 9 to 13 to 11, and add a crystallization solvent such as chlorobenzene, nitrobenzene, toluene, orthochlorotoluene, xylene or an aqueous emulsion of the solvent to 100 parts by weight of crude phthalocyanine green in the amount of solvent. Add 10 to 20 parts by weight. Furthermore, the system is heated, stirred, passed through two mouths, 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９
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９食塩など
の無機塩１００〜１０００重量部。Phthalocyanine green processed by crystallization solvent method is 9
It is then wet milled. Wet grinding involves 100 parts by weight of phthalocyanine green treated by a crystallization solvent method, 9 parts by weight of an inorganic salt such as common salt, and 100 to 1000 parts by weight.
ジエチレングリコールなどの湿潤剤３０〜３００重量部
をニーダ−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。30 to 300 parts by weight of a wetting agent such as diethylene glycol are mixed in a kneader or the like, and the mixture is ground under heating and then poured into water or a dilute acid aqueous solution.
無機塩、湿潤剤を溶解し１口過、水洗してウェットケー
キ顔料を得るか、さらに乾燥してドライバウダー顔料を
得るものである。The inorganic salt and wetting agent are dissolved, passed through one sip, and washed with water to obtain a wet cake pigment, or further dried to obtain a dry powder pigment.
本発明で製造された顔料は、塗料、印刷インキ。The pigment produced by the present invention can be used in paints and printing inks.
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。It has high coloring power when used as a coloring agent for resins. In particular, when printing inks are made from dry powder pigments, they exhibit excellent coloring power.
次に本発明を実施例により説明する。例中「部」、「％
」とは２重量部１重量％をそれぞれ示す。Next, the present invention will be explained by examples. In examples, "part", "%"
” indicates 2 parts by weight and 1% 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
アニンク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。つぎに攪拌下、水産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３１０
．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時間攪拌
した後９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２
００部。Example 1 Crude phthalocyanine clean wet cake (pigment content 40%) obtained by anhydrous aluminum chloride method in water 250
A slurry of 7% crude phthalocyanine green was prepared. Next, while stirring, sodium aquatic acid was added to adjust the pH of the slurry to 11-11°. and 13 parts of xylene, nonionic surfactant (Nonal 310
．． An emulsion containing 8 parts of Toho Chemical Industry Co., Ltd.)) and 15 parts of water was added, heated, stirred at 80 to 90°C for 1 hour, filtered through 9 filtration, washed with water, and dried to obtain phthalocyanine green. 100 parts of this phthalocyanine green and 2 parts of salt
00 copies.
ジエチレングリコール６０部をニーグー中で混合し、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’Ｃで１時間攪
拌し９口過、水洗、乾燥してフタロシアニングリーン顔
料を得た。Mix 60 parts of diethylene glycol in a Nigu,
After milling for 6 hours at 10-120°C, the mixture was reduced to 0.
The mixture was poured into a 5% aqueous sulfuric acid solution, stirred at 80 to 90'C for 1 hour, filtered through 9 mouths, washed with water, and dried to obtain a phthalocyanine green pigment.
比較例１
粗製フタロシアニングリーン１００部、食ｍ２００部、
ジエチレングリコール６０部をニーダ−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時間攪拌
し１口過、水洗、乾燥してフタロシアニングリーン顔料
を得た。Comparative Example 1 100 parts of crude phthalocyanine green, 200 parts of food m,
Mix 60 parts of diethylene glycol in a kneader and add 1
After milling for 6 hours at 10-120°C, the mixture was reduced to 0.
The mixture was poured into a 5% aqueous sulfuric acid solution, stirred at 80 to 90°C for 1 hour, filtered once, 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
性フェノール樹脂フェス中に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 face using a three-roll mill.
Manufactured offset ink.
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（日本重色工業製）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。Testing the offset inks of Example 1 and Comparative Example 1,
When the coloring power of the pigments was compared using a colorimeter-color machine (manufactured by Nippon Heavy Industries), it was found that the pigment of Comparative Example 1 was 100%
In Example 1, it was 120%.
また、実施例１および比較例１の顔料を、それぞれライ
ムロジン系フェスにボールミルで分散させ。Further, the pigments of Example 1 and Comparative Example 1 were each dispersed in a lime rosin festival using a ball mill.
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９着色力が１５部程度向上していた。Manufactured gravure ink. The pigment of Example 1 had an improved tinting strength of about 15 parts compared to the pigment of Comparative Example 1.
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時間攪拌した後、４
０００部の水に流入させ、８０℃で１時間かくはんし２
口過、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
00 parts and stirred at 15 to 20°C for 4 hours.
000 parts of water and stirred at 80℃ for 1 hour.
A 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 using this pigment in the same manner as in Example 1, it showed almost the same coloring power as 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。次に水蒸気蒸留によりキシレンを除去した後１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%), 150 parts of xylene, 4 parts of an anionic surfactant (oleic acid manufactured by Soken Chemical Co., Ltd.), and 8 parts of sodium hydroxide were mixed, heated, and maintained at the boiling point for 6 hours. Next, xylene was removed by steam distillation, followed by one filtration, washing with water, and drying 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 offset ink was produced using this pigment in the same manner as in Example 1, it showed a coloring strength 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。Example 2 Solvent treatment was carried out in the same manner as in Example 1, except that 20 parts of toluene was used instead of 13 parts of xylene.
湿式摩砕処理して顔料を得た。A pigment was obtained by wet milling.
この顔料の着色力は、実施例１と同様、１２０％であっ
た。The coloring power 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１食塩４００部、ジエチレングリコール１０
０部をニーグー中で混合し、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 Same as Example 1, 100 parts of solvent-treated phthalocyanine green, 400 parts of common salt, 10 parts of diethylene glycol.
0 parts were mixed in a Niguu, ground at 110-120°C for 4 hours, and then 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 coloring power of this pigment was 120% compared to 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
ニンブリーフ１００部９食塩４００部。Example 4 100 parts of phthalocyanine briefs and 400 parts of common salt were treated in the same manner as in Example 1 except that 20 parts of xylene was used instead of 13 parts of xylene in Example 1.
ジエチレングリコール１００部をニーグー中で混合し、
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。Mix 100 parts of diethylene glycol in a nigu,
After grinding at 110-120° 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 coloring power of this pigment was 120% compared to Comparative Example 1.
手続補正書（自発） 昭和６２年 ６月、４日Procedural amendment (voluntary) June 4, 1986
Claims (1)
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。 ２、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。[Claims] 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 using a grinding aid. . 2. A method for producing a phthalocyanine green pigment according to claim 1, which uses crude phthalocyanine green obtained by halogenating phthalocyanine in a eutectic mixture of anhydrous aluminum chloride and sodium chloride.
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 true JPS63101459A (en) | 1988-05-06 |
| JPH064775B2 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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005065298A3 (en) * | 2003-12-31 | 2007-03-29 | Sun Chemical Corp | Process for conditioning azo pigments |
| JP2007332302A (en) * | 2006-06-16 | 2007-12-27 | Dainippon Ink & Chem Inc | Method for producing chlorinated metal phthalocyanine pigment |
| JP2008285532A (en) * | 2007-05-16 | 2008-11-27 | Toyo Ink Mfg Co Ltd | Fine polyhalogenated phthalocyanine pigment, method for producing the same and colored composition produced by using the same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0695596A (en) * | 1992-07-29 | 1994-04-08 | Abisare:Kk | Electrostatic notice device |
-
1986
- 1986-10-17 JP JP24550086A patent/JPH064775B2/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005065298A3 (en) * | 2003-12-31 | 2007-03-29 | Sun Chemical Corp | Process for conditioning azo pigments |
| JP2007332302A (en) * | 2006-06-16 | 2007-12-27 | Dainippon Ink & Chem Inc | Method for producing chlorinated metal phthalocyanine pigment |
| JP2008285532A (en) * | 2007-05-16 | 2008-11-27 | Toyo Ink Mfg Co Ltd | Fine polyhalogenated phthalocyanine pigment, method for producing the same and colored composition produced by using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH064775B2 (en) | 1994-01-19 |
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