JPS5989361A - Preparation of clear copper phthalocyanine pigment - Google Patents
Preparation of clear copper phthalocyanine pigmentInfo
- Publication number
- JPS5989361A JPS5989361A JP16313282A JP16313282A JPS5989361A JP S5989361 A JPS5989361 A JP S5989361A JP 16313282 A JP16313282 A JP 16313282A JP 16313282 A JP16313282 A JP 16313282A JP S5989361 A JPS5989361 A JP S5989361A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- copper phthalocyanine
- copper
- phthalocyanine pigment
- copper salt
- 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
- 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 title claims abstract description 16
- 239000000049 pigment Substances 0.000 title claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 150000001879 copper Chemical class 0.000 claims abstract description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000004202 carbamide Substances 0.000 claims abstract description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims abstract description 5
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229920006391 phthalonitrile polymer Polymers 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000004996 alkyl benzenes Chemical class 0.000 abstract description 11
- PIUUDKDOAUICQP-UHFFFAOYSA-N 2-methylpentan-2-ylbenzene Chemical compound CCCC(C)(C)C1=CC=CC=C1 PIUUDKDOAUICQP-UHFFFAOYSA-N 0.000 abstract description 2
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000010891 toxic waste Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 13
- 235000019646 color tone Nutrition 0.000 description 7
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- GDEQPEBFOWYWSA-UHFFFAOYSA-N 1,2-dimethyl-3-propan-2-ylbenzene Chemical group CC(C)C1=CC=CC(C)=C1C GDEQPEBFOWYWSA-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003672 ureas Chemical group 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は鮮明々色調をもつ銅フタロシアニン顔料の製造
法に関するもので、無害な溶剤を使用する新規な製造法
である。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing copper phthalocyanine pigments with vivid color tones, and is a novel method for producing copper phthalocyanine pigments using harmless solvents.
銅フタロシアニン顔料は色調が美しいこと、着野で広く
使用され、多量に生産されている。Copper phthalocyanine pigments have beautiful colors, are widely used in Chikuno, and are produced in large quantities.
銅フタロシアニン顔料の製造法には、（１）フタロニト
リルと銅または銅塩との反応、（２）触媒の存在下にお
けるフタル酸、無水フタール酸またはフタルイミド等と
尿素及び銅または銅塩との反応、（３）オルソシアノベ
ンズアミドと銅または銅塩との反応、（４）無金属フタ
ロシアニンと銅塩との反応等多くの方法が知られている
。工業的製造法としては、フタロニトリルと銅塩とをニ
トロベンゼン等の反応に不活性な溶剤中で反応させる二
） ＩＪシル溶剤法よび無水フタル酸、尿素および銅塩
をニトロベンゼンまたはトリクロルベンゼン等の溶剤中
で反応させるフタル酸溶剤法が多く用いられている。The method for producing copper phthalocyanine pigments includes (1) reaction of phthalonitrile with copper or copper salt, (2) reaction of phthalic acid, phthalic anhydride, phthalimide, etc. with urea and copper or copper salt in the presence of a catalyst. Many methods are known, such as (3) reaction of orthocyanobenzamide with copper or a copper salt, and (4) reaction of metal-free phthalocyanine with copper salt. Industrial production methods include the 2) IJ sil solvent method, in which phthalonitrile and copper salt are reacted in a solvent inert to the reaction, such as nitrobenzene, and phthalic anhydride, urea, and copper salt are reacted in a solvent such as nitrobenzene or trichlorobenzene. A phthalic acid solvent method is often used.
これらの溶剤法は、前記のととくクロルベンゼン等を用
いるために毒性または臭気のため公害の原因となシ、ま
た作業場の衛生上にも好ましくなく、その解決が望まれ
ている。Since these solvent methods use chlorobenzene and the like as mentioned above, they are toxic and odor-causing, causing pollution, and are also unfavorable in terms of workplace hygiene, and a solution to these problems is desired.
これらの問題に対処して、特開昭４９−６３７３５およ
び特開昭４９−１１６１２１に少なくとも１個のプロピ
ル基を有するポリアルキルベンゼンのごときアルキルベ
ンゼンを溶剤とする方法が提案されているが、これらの
方法を本発明者等が実施した結果、粗製銅フタロシアニ
ンの色調が汚れ不鮮明で満足な結果をうろことができな
い。特に粗製銅フタロシアニンの色調が不鮮明であるこ
とは、塗料および印刷インキ等に使用する際の致命的欠
点となる。To deal with these problems, methods using an alkylbenzene such as polyalkylbenzene having at least one propyl group as a solvent have been proposed in JP-A-49-63735 and JP-A-49-116121. As a result of carrying out the method by the present inventors, the color tone of the crude copper phthalocyanine was stained and unclear, making it impossible to obtain a satisfactory result. In particular, the unclear color tone of crude copper phthalocyanine is a fatal drawback when used in paints, printing inks, and the like.
本発明者等は、この問題を解決するため無害の溶剤を調
査検討し、食品衛生上、環境衛生」二無害なものがある
ことに着目し、その使用について研究し、本発明を完成
した。In order to solve this problem, the present inventors researched and considered harmless solvents, and focused on the fact that there were solvents that were harmless in terms of both food hygiene and environmental hygiene, researched their use, and completed the present invention.
従来の溶剤を単にこの分野の溶剤として公知の上記のご
ときアルキルベンゼンに変換して反応せしめると、得ら
れる銅フタロシアニンの色調が不鮮明で実用できない。If a conventional solvent is simply converted into the above-mentioned alkylbenzene, which is known as a solvent in this field, and reacted, the color tone of the resulting copper phthalocyanine will be indistinct and cannot be put to practical use.
本発明者等は、鮮明な色調の粗製銅フタロシアニンを合
成するために各種の構造を有するアルキルベンゼンにつ
いて研究し〜た結果、特定の構造のアルキルベンゼン溶
剤中で、反応を行なうことにより、従来の溶剤を使用し
て合成した粗製フタロ７アニンよりも色調の鮮明な銅フ
タロシアニン顔料が得られることを発見した。The present inventors conducted research on alkylbenzenes with various structures in order to synthesize crude copper phthalocyanine with a vivid color tone. As a result, the inventors conducted a reaction in an alkylbenzene solvent with a specific structure, and found that conventional solvents could be It was discovered that a copper phthalocyanine pigment with a clearer color tone than the crude phthalocyanine synthesized using the method was obtained.
すなわち本発明は、前記の二） ＩＪル溶剤法、フタル
酸溶剤法において、溶剤として下記一般式のアルキルベ
ンゼンを使用し、反応せしめるものである。That is, the present invention uses an alkylbenzene of the following general formula as a solvent in the above-mentioned 2) IJ solvent method and phthalic acid solvent method to carry out the reaction.
一般式
（式中Ｒは、炭素数が３のアルキル基を示す。）本発明
によれば、溶剤として、無害のアルキルベンゼンを使用
するだめの作業場の環境衛生の改善および公害防止に役
立ち、しかも従来法に優る色調のよい銅フタロ７アニン
顔料を得るもので、実用上の価値犬なものである。According to the present invention, the general formula (R in the formula represents an alkyl group having 3 carbon atoms) is useful for improving environmental hygiene and preventing pollution in workplaces where harmless alkylbenzene is used as a solvent. This method yields a copper phthalo-7-anine pigment with better color tone than the standard, and is of great practical value.
本発明に使用する溶剤は、前記一般式で表わされるアル
キルベンゼンで、単独もしくは混合して、または他の溶
剤と混合して使用する。The solvent used in the present invention is an alkylbenzene represented by the above general formula, and is used alone or in combination, or in combination with other solvents.
本発明は無害のアルキルベンゼンを溶剤として使用し、
反応せしめるもので溶剤の使用量は従来法と同様でよい
。また反応は、必要があれば加圧して行なってもよい。The present invention uses harmless alkylbenzene as a solvent,
The amount of solvent used for the reaction may be the same as in the conventional method. Further, the reaction may be carried out under pressure if necessary.
加圧の程度は２ ｋｙ ／ ｃｍ２程度の圧力から効果
があり、３ｋｇ／６ｎ２以上が好結果を得るが、実用上
１．０ ｋｙ ／ ｃｍｚ位捷で実施する。加圧の方法
は、オートクレーブ等の密閉容器中で加熱し反応せしめ
、発生するガスおよび蒸気の圧力を利用する。反応器に
は調節しうるガス放出口を設け、これより一部のガスま
たは蒸気を放出することにより反応器中の圧力を調節す
る。加圧下に反応を行うことは、尿素類の分解を抑制し
、銅フタロンアニンの収量の増大が図れ、かつ熱エネル
ギー損失を低減できるので好ましい。The degree of pressurization is effective from a pressure of about 2 ky/cm2, and good results are obtained with a pressure of 3 kg/6n2 or more, but in practice it is carried out at a pressure of about 1.0 ky/cm2. The pressurization method utilizes the pressure of gas and steam generated by heating and reacting in a closed container such as an autoclave. The reactor is provided with an adjustable gas outlet through which a portion of the gas or vapor is released to adjust the pressure in the reactor. It is preferable to carry out the reaction under pressure because it suppresses the decomposition of ureas, increases the yield of copper phthalonanine, and reduces thermal energy loss.
次に実施例を示す。実施例中の部は重量部を示ずＯ
実施例１
フタルイミド６０部、尿素６０部、無水塩化第一銅１０
部、モリブデン酸アンモニウム００１部、ｔｅｒｔ−ヘ
キシルベンゼン２００部を１９０〜１９５℃に３時間加
熱せしめた。Next, examples will be shown. Parts in Examples do not indicate parts by weight.O Example 1 60 parts of phthalimide, 60 parts of urea, 10 parts of anhydrous cuprous chloride
1 part, ammonium molybdate, and 200 parts of tert-hexylbenzene were heated to 190 to 195°C for 3 hours.
冷却後反応物を取出し、メタノール４００部で洗い溶剤
を除き、さらに２チカセイソーダ水溶液４１中で１時間
煮沸後ろ過、水洗し、２チ塩酸２４中で同様に処理し、
ろ過、水洗し９０℃〜１００℃にて乾燥し、銅フタロシ
アニン顔料５３部を得た・このものは鮮明な青色を有し
、従来の溶剤法で得られたものよりも鮮明であった。次
にその比較を示す。比較に用いた製品は、溶剤としてニ
トロベンゼン、イングロビルトルエン、ジイソゾロピル
トルエンおよびイソプロピルキシレンを使用し、他の条
件を本実施例と同様にしたもの（すなわち従来法）であ
る。々お、試料はフタロシアニン顔料１部、チタンホワ
イ）Ｒ−８２０１０部を不揮発分６０チのアルキッドワ
ニス１７部と混合し得られる塗料を展色し、測色した。After cooling, the reaction product was taken out, washed with 400 parts of methanol to remove the solvent, and further boiled for 1 hour in a 2% sodium hydroxide solution, filtered, washed with water, and treated in the same manner in 2% hydrochloric acid 24%.
Filtration, washing with water, and drying at 90°C to 100°C yielded 53 parts of copper phthalocyanine pigment.This product had a clear blue color, which was brighter than that obtained by the conventional solvent method. The comparison is shown next. The product used for comparison was one in which nitrobenzene, inglobiltoluene, diisozolopyltoluene, and isopropylxylene were used as solvents, and other conditions were the same as in this example (ie, conventional method). Each sample was prepared by mixing 1 part of phthalocyanine pigment and 10 parts of titanium white R-820 with 17 parts of alkyd varnish having a non-volatile content of 60 parts, and the resulting paint was spread and measured.
結果を表に示す。The results are shown in the table.
度が高かった。The degree was high.
実施例２
実施例１の無水塩化第一銅４４部を無水硫酸銅７１部に
変え、他は同様に反応せしめて同様な銅フタロシアニン
顔料を得り。Example 2 A similar copper phthalocyanine pigment was obtained by replacing 44 parts of anhydrous cuprous chloride in Example 1 with 71 parts of anhydrous copper sulfate and reacting in the same manner as described above.
特許出願人 日本石油化学株式会社
特許出願人 東洋インキ製造株式会社代理人 弁理士
伊 東 辰 雄代理人 弁理士 伊 東
哲 也第１頁の続き
■発 明 者 石塚千吾
東京都中央区京橋２丁目３番１３
号東洋インキ製造株式会社内
（ｎ）発 明 者 鈴木明光
東京都中央区京橋２丁目３番１３
号東洋インキ製造株式会社内
＠出 願 人 東洋インキ製造株式会社東京都中央区京
橋２丁目３番１３
号Patent applicant Japan Petrochemical Co., Ltd. Patent applicant Toyo Ink Mfg. Co., Ltd. Agent Patent attorney Tatsuo Ito Agent Patent attorney Tetsuya Ito Continued from page 1 Inventor Chigo Ishizuka 2, Kyobashi, Chuo-ku, Tokyo No. 3-13 Toyo Ink Manufacturing Co., Ltd. (n) Inventor Akiko Suzuki No. 2-3-13 Kyobashi, Chuo-ku, Tokyo Toyo Ink Manufacturing Co., Ltd. @ Applicant Toyo Ink Manufacturing Co., Ltd. Kyobashi, Chuo-ku, Tokyo 2-3-13
Claims (1)
はフタロニトリルもしくはその誘導体と銅塩を溶剤中で
加熱反応せしめて銅フタロシアニンを製造する方法にお
いて、一般式 （式中Ｒは炭素数が３のアルキル基を示す。）で示され
る化合物を単独もしくは混合して反応溶剤として使用す
ることを特徴とする銅フタロシアニン顔料の製造法。[Claims] A method for producing copper phthalocyanine by subjecting phthalic anhydride or its derivatives, urea and a copper salt, or phthalonitrile or its derivatives and a copper salt to a heating reaction in a solvent, in which the general formula (in the formula R represents an alkyl group having 3 carbon atoms.) A method for producing a copper phthalocyanine pigment, characterized in that a compound represented by the following formula is used alone or in combination as a reaction solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16313282A JPS5949259B2 (en) | 1982-09-21 | 1982-09-21 | Method for producing vivid copper phthalocyanine pigments |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16313282A JPS5949259B2 (en) | 1982-09-21 | 1982-09-21 | Method for producing vivid copper phthalocyanine pigments |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11429075A Division JPS5842219B2 (en) | 1975-09-23 | 1975-09-23 | Method for producing vivid copper phthalocyanine pigments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5989361A true JPS5989361A (en) | 1984-05-23 |
| JPS5949259B2 JPS5949259B2 (en) | 1984-12-01 |
Family
ID=15767797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16313282A Expired JPS5949259B2 (en) | 1982-09-21 | 1982-09-21 | Method for producing vivid copper phthalocyanine pigments |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5949259B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1038760C (en) * | 1990-11-12 | 1998-06-17 | 上海染料化工十二厂 | Solvent method for production of raw copper phthalocyanine |
| KR20020077947A (en) * | 2001-04-03 | 2002-10-18 | 삼협자원개발 주식회사 | Production Method of Solvent for the Synthesis of Copper Phthalocyanine |
-
1982
- 1982-09-21 JP JP16313282A patent/JPS5949259B2/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1038760C (en) * | 1990-11-12 | 1998-06-17 | 上海染料化工十二厂 | Solvent method for production of raw copper phthalocyanine |
| KR20020077947A (en) * | 2001-04-03 | 2002-10-18 | 삼협자원개발 주식회사 | Production Method of Solvent for the Synthesis of Copper Phthalocyanine |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5949259B2 (en) | 1984-12-01 |
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