JPS5917742B2 - Manufacturing method of bisazomethine pigments - Google Patents
Manufacturing method of bisazomethine pigmentsInfo
- Publication number
- JPS5917742B2 JPS5917742B2 JP10697072A JP10697072A JPS5917742B2 JP S5917742 B2 JPS5917742 B2 JP S5917742B2 JP 10697072 A JP10697072 A JP 10697072A JP 10697072 A JP10697072 A JP 10697072A JP S5917742 B2 JPS5917742 B2 JP S5917742B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- pigment
- bisazomethine
- dicarboxylic acid
- pigments
- 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
Links
- 239000000049 pigment Substances 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 1,2-dicarboxylic acid imides Chemical class 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 9
- 150000004984 aromatic diamines Chemical class 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- XQFYGXFPKONEPY-UHFFFAOYSA-N 2,3-diphenylfuran Chemical group O1C=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 XQFYGXFPKONEPY-UHFFFAOYSA-N 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000004040 coloring Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000010298 pulverizing process Methods 0.000 description 6
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000001052 yellow pigment Substances 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- QRKVRHZNLKTPGF-UHFFFAOYSA-N phosphorus pentabromide Chemical group BrP(Br)(Br)(Br)Br QRKVRHZNLKTPGF-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Description
【発明の詳細な説明】
本発明は新規なビスアゾメチン系顔料の製法に■０ 係
るものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a novel bisazomethine pigment.
本発明は耐光性、耐熱性、耐油性、耐薬品性等の諸堅牢
度が非常に優れており、大きな着色力を有する鮮明な黄
色系色調の下記一般式で表わされる新規なビスアゾメチ
レン系顔料を製造する方法を提供することを目的とする
。Ｎ−Ｒ−Ｎ
ψ凸ｉ゛−（Ｔ東
・・・・・・〔■〕
■５
（式中、Ｒはフェニレン基、ジフェニル基又はジフェニ
ルフラン基を示し、Ｘはハロゲン原子を示し、ｎはＯ〜
２の数を示す。The present invention is a novel bisazomethylene series represented by the following general formula, which has excellent fastness properties such as light resistance, heat resistance, oil resistance, and chemical resistance, and has a clear yellowish tone with great coloring power. An object of the present invention is to provide a method for producing pigments. N-R-N ψ convex i゛-(T east... [■] ■5 (In the formula, R represents a phenylene group, diphenyl group or diphenylfuran group, X represents a halogen atom, n is O~
Indicates the number 2.
）本発明の上記目的は、一般式
（式中、Ｘはハロゲン原子を示し、ｎはＯ〜２の数を示
す。) The above object of the present invention is achieved by the general formula (wherein, X represents a halogen atom, and n represents the number of O~2).
）で表わされるナフタリン−１・２−ジカルボン酸イミ
２ド類を不活性溶媒の存在下でハロゲン化処理し、次い
で芳香族ジアミン類と縮合させることにより達成される
。) is achieved by halogenating the naphthalene-1,2-dicarboxylic acid imides represented by 2 in the presence of an inert solvent, and then condensing it with aromatic diamines.
本発明をさらに詳細に説明する。The present invention will be explained in further detail.
本発明の原料の一つとして使用される前示一般式〔１〕
で表わされるナフタリン−ジカルボン酸イミド誘導体と
しては、例えば、ナフタリン−１・２−ジカルボン酸イ
ミド、モノクロルナフタリンー１・２−ジカルボン酸イ
ミド、モノブロムナフタリン−１・２−ジカルボン酸イ
ミド、ジクロルナフタリン−１・２−ジカルボン酸イミ
ド、ジブロムナフタリン−１・２−ジカルボン酸イミド
等が挙げられる。General formula [1] used as one of the raw materials of the present invention
Examples of naphthalene-dicarboxylic imide derivatives represented by include naphthalene-1,2-dicarboxylic imide, monochloronaphthalene-1,2-dicarboxylic imide, monobromnaphthalene-1,2-dicarboxylic imide, and dichlornaphthalene-1,2-dicarboxylic imide. -1,2-dicarboxylic acid imide, dibromnaphthalene-1,2-dicarboxylic acid imide, and the like.
本発明においては、上述のナフタリン−１・２−ジカル
ボン酸イミド類を、まず、不活性溶媒中でハロゲン化処
理するものである。In the present invention, the above-mentioned naphthalene-1,2-dicarboxylic acid imide is first subjected to a halogenation treatment in an inert solvent.
不活性溶媒としては、例えば、０−ジクロルベンゼン、
トリクロルベンゼン、０−ニトロトルエン、ニトロベン
ゼン、クロルナフタリン、クロルベンゼン等が挙げられ
、その使用量は前示一般式〔１〕で表わされるナフタリ
ン−１・２−ジカルボン酸イミド類に対し、５〜２０倍
量（重量）程度でよい。また、ハロゲン化剤としては、
五塩化リン、五臭化リン、三塩化リン、三臭化リン等が
好ましく、ナフタリン−１・２−ジカルボン酸イミド類
に対し、１〜５倍量（重量）使用される。上記ハロゲン
化処理によつて、後続する芳香族ジアミンとの縮合反応
が極めて円滑に実施される。本法に使用される芳香族ジ
アミン類としては一般式（式中、Ｒはフエニレン基、ジ
フエニル基又はジフエニルフラン基を示す。Examples of the inert solvent include 0-dichlorobenzene,
Examples include trichlorobenzene, 0-nitrotoluene, nitrobenzene, chlornaphthalene, chlorobenzene, etc., and the amount used is 5 to 20 times that of the naphthalene-1,2-dicarboxylic acid imide represented by the general formula [1] above. The amount (weight) is sufficient. In addition, as a halogenating agent,
Phosphorus pentachloride, phosphorus pentabromide, phosphorus trichloride, phosphorus tribromide, etc. are preferred, and are used in an amount of 1 to 5 times (by weight) the amount of naphthalene-1,2-dicarboxylic acid imide. The halogenation treatment allows the subsequent condensation reaction with the aromatic diamine to be carried out extremely smoothly. The aromatic diamines used in this method have the general formula (wherein R represents a phenylene group, a diphenyl group, or a diphenylfuran group).
）で表わされる各種のジアミン類が挙げられる。) Various diamines represented by:
具体的には、例えば、ｐ−またはｍ−フエニレンジアミ
ン、ベンジジンあるいは示される芳香族ジアミン類が挙
げられる。Specific examples include p- or m-phenylenediamine, benzidine, and the aromatic diamines shown below.
ナフタリン−１・２−ジカルボン酸イミド類は通常芳香
族ジアミン類に対し、２〜１０倍モル量使用することが
できるが、経済的には２〜２．５倍モル量が有利である
。Naphthalene-1,2-dicarboxylic acid imide can be used in a molar amount 2 to 10 times the amount of aromatic diamine, but economically, a molar amount of 2 to 2.5 times is advantageous.
反応温度としては特に限られるものではないが、通常８
０〜２００℃、特に１００〜１５０℃が好ましい。The reaction temperature is not particularly limited, but is usually 8.
0 to 200°C, particularly 100 to 150°C is preferred.
反応混合物より目的生成物であるビスアゾメチン系顔料
を取得するには、前記不活性溶媒中で反応後、冷却して
反応生成物を析出させ、濾過し、エタノール、エタノー
ル等で洗滌する。To obtain the desired bisazomethine pigment from the reaction mixture, the reaction product is reacted in the inert solvent, cooled to precipitate the reaction product, filtered, and washed with ethanol, ethanol, etc.
あるいは反応混合物を冷却後、メタノール、エタノール
等の希釈剤を用いて希釈し、析出したケーキを濾取、洗
滌すればよい。かくして得られたケーキは微粉砕するこ
とにより、そのまま着色用顔料として充分使用可能であ
るが、さらに公知の顔料化方法、例えばメタノール、エ
タノール等のビスアゾメチン系顔料をほとんど溶解しな
い媒体に分散させ、高速分散機等で微粉砕する等、によ
り処理を行うと高品位の顔料が得られる。以上のように
して得られるビスアゾメチン系顔料は、いずれも新規物
質であり、塗料用、印刷インク用およびプラスチツク用
顔料として耐光性、耐熱性、耐油性、耐薬品性等諸堅牢
性に優れた鮮明な黄色〜橙色系色調を有する。Alternatively, after cooling the reaction mixture, it may be diluted with a diluent such as methanol or ethanol, and the precipitated cake may be collected by filtration and washed. By finely pulverizing the cake thus obtained, it can be used as it is as a coloring pigment. However, it can also be used by known pigmentation methods, such as dispersing it in a medium that hardly dissolves bisazomethine pigments, such as methanol or ethanol. A high-quality pigment can be obtained by processing the pigment by pulverizing it with a high-speed dispersion machine or the like. The bisazomethine pigments obtained in the above manner are all new substances, and have excellent fastness such as light resistance, heat resistance, oil resistance, and chemical resistance as pigments for paints, printing inks, and plastics. It has a bright yellow to orange color tone.
次に、本発明を実施例によりさらに詳細に説明するが、
本発明はその要旨を超えない限り以下の実施例により限
定されるものではない。Next, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited to the following examples unless it exceeds the gist thereof.
尚、実施例中「部」とあるは「重量部」を示す。トリク
ロルベンゼン２０部中に、ジブロムナフタリン−１・２
−ジカルボン酸イミド３．６部および五塩化リン２．３
部の微粉末を分散させ１２０〜１２５℃で７０分間攪拌
した。In addition, "parts" in the examples indicate "parts by weight." In 20 parts of trichlorobenzene, dibromnaphthalene-1 and 2
- 3.6 parts of dicarboxylic acid imide and 2.3 parts of phosphorus pentachloride
part of the fine powder was dispersed and stirred at 120 to 125°C for 70 minutes.
反応の進行に伴い混合物は次第に溶解し、暗赤色を呈し
た。液温を約１１０℃に冷却し、０．５部のｐ−フエニ
レンジアミンを２０部のトリクロルベンゼンに溶解した
液を加えると顔料が直ちに析出した。As the reaction progressed, the mixture gradually dissolved and took on a dark red color. When the liquid temperature was cooled to about 110° C. and a solution of 0.5 parts of p-phenylenediamine dissolved in 20 parts of trichlorobenzene was added, the pigment immediately precipitated.
同温度でさらに３時間反応させた後、室温まで冷却、濾
過し、熱メタノールで洗滌、乾燥することにより、下記
構造式を有する生成物２．１部を得た。このものは融点
３００℃以上であり、元素分析結果は下記表１の通り、
計算値とほぼ一致した。この生成物は微粉砕することに
よりそのまま着色用顔料として充分使用可能であるが、
さらに２０倍量のメタノールに懸濁し、ホモミキサー（
特殊機化製高速分散機）で１０時間ミリングすることに
より、さらに高品位のビスアゾメチン系顔料が得られた
。本顔料をペイントおよびプラスチツク中に配合したと
ころ、耐熱性、耐光性、耐薬品性の諸堅牢性に優れた鮮
明黄色色調を有する製品が得られた。After further reacting at the same temperature for 3 hours, the reaction mixture was cooled to room temperature, filtered, washed with hot methanol, and dried to obtain 2.1 parts of a product having the following structural formula. This material has a melting point of 300℃ or higher, and the elemental analysis results are as shown in Table 1 below.
It almost agreed with the calculated value. This product can be used directly as a coloring pigment by finely pulverizing it, but
Further, suspend in 20 times the amount of methanol and use a homomixer (
By milling for 10 hours using a high-speed dispersion machine manufactured by Tokushu Kika Co., Ltd., a bisazomethine pigment of even higher quality was obtained. When this pigment was blended into paints and plastics, products with a bright yellow tone and excellent heat resistance, light resistance, and chemical resistance were obtained.
実施例 ２０−ジクロルベンゼン２０部中にジブロムナ
フタリン−１・２−ジカルボン酸イミド３．６部及び五
塩化リン２．３部の微粉末を分散させ１４０〜１５０℃
で７０分攪拌した。Example 2 Fine powder of 3.6 parts of dibromnaphthalene-1,2-dicarboxylic acid imide and 2.3 parts of phosphorus pentachloride was dispersed in 20 parts of 0-dichlorobenzene at 140-150°C.
The mixture was stirred for 70 minutes.
反応の進行と共に混合物は次第に溶解して暗赤色を呈し
た。液温を約１１０℃に冷却し、０．９部のベンジジン
をＯ−ジクロルベンゼンに分散した液を加えると顔料が
直ちに析出した。As the reaction progressed, the mixture gradually dissolved and took on a dark red color. When the liquid temperature was cooled to about 110° C. and a liquid prepared by dispersing 0.9 parts of benzidine in O-dichlorobenzene was added, the pigment immediately precipitated.
同温度に更に３時間反応させた後室温まで冷却、濾過し
、熱メタノールで洗滌、乾燥することにより、下記構造
式を有する生成物２．２部を得た。After reacting at the same temperature for an additional 3 hours, the reaction mixture was cooled to room temperature, filtered, washed with hot methanol, and dried to obtain 2.2 parts of a product having the following structural formula.
このものは融点３００′Ｃ以上で元素分析結果は下記表
の通り計算値とほぼ一致した。この生成物は微粉砕する
ことにより、そのまま着色用顔料として充分使用可能で
あるが、更に２０倍量のメタノールに懸濁し１５倍量の
メデイア（オツタワサンド：直径０．２〜１．２ＴｒＬ
／ＲｒＬ）と共にサンド・グラインダーにて１０時間ミ
リングすることにより更に高品位のビスアゾメチン系顔
料を得た。This material had a melting point of 300'C or higher, and the elemental analysis results almost agreed with the calculated values as shown in the table below. By finely pulverizing this product, it can be sufficiently used as a coloring pigment as it is, but it can also be suspended in 20 times the amount of methanol and made into a 15 times amount of media (Otsutawa Sand: diameter 0.2 to 1.2 TrL).
/RrL) in a sand grinder for 10 hours to obtain a higher quality bisazomethine pigment.
本顔料は大きな着色力を有し、また耐熱性、耐光性、耐
薬品性に優れており、塗料、印刷インキ及びプラスチッ
クの着色に適する。This pigment has great coloring power and excellent heat resistance, light resistance, and chemical resistance, making it suitable for coloring paints, printing inks, and plastics.
実施例 ３
クロルベンゼン２０部中にモノクロルナフタリン−１・
２−ジカルボン酸イミド２．３部及び五臭化リン４．８
部の微粉末を分散させ、１２０〜１２５℃で７０分攪拌
した。Example 3 Monochloronaphthalene-1 in 20 parts of chlorobenzene.
2.3 parts of 2-dicarboxylic acid imide and 4.8 parts of phosphorus pentabromide
part of the fine powder was dispersed and stirred at 120 to 125°C for 70 minutes.
反応の進行と共に混合物は次第に溶解して暗赤色を呈し
た。液温を約１１０℃に冷却し、０．５部のｐ−フエニ
レンジアミンを２０部のクロルベンゼンに溶解した液を
加えると、顔料が直ちに析出した。As the reaction progressed, the mixture gradually dissolved and took on a dark red color. When the liquid temperature was cooled to about 110° C. and a solution containing 0.5 parts of p-phenylenediamine dissolved in 20 parts of chlorobenzene was added, the pigment immediately precipitated.
同温度で更に３時間反応させた後室温まで冷却濾過し、
熱メタノールで洗滌、乾燥することにより下記構造式を
有する生成物１．２部を得た。このものは融点３００℃
以上で元素分析結果は下記表の通り計算値とほぼ一致［
．た。After reacting at the same temperature for another 3 hours, it was cooled to room temperature and filtered.
By washing with hot methanol and drying, 1.2 parts of a product having the following structural formula was obtained. This substance has a melting point of 300℃
The above elemental analysis results almost match the calculated values as shown in the table below [
．． Ta.
この生成物は微粉砕することにより、そのまま着色用顔
料として充分使用可能であるが、更に２０倍量のメタノ
ールに懸濁し、ホモミキサー（特殊機化製高速分散機）
で１０時間ミリングすることにより一層鮮明な着色力の
大きい黄色顔料微粉末を得た。By finely pulverizing this product, it can be used directly as a coloring pigment, but it is further suspended in 20 times the amount of methanol and mixed with a homomixer (high-speed dispersion machine manufactured by Tokushu Kika).
By milling for 10 hours, a fine yellow pigment powder with even clearer coloring power was obtained.
本顔料は鮮明な黄色色調を与え、大きな着色力と優れた
耐光性、耐熱性、耐油性を有し、特に塩化ビニル、ポリ
エチレン、ポリスチレン、ＡＢＳ樹脂等のプラスチック
着色用に適している。This pigment gives a vivid yellow tone, has high coloring power, and excellent light resistance, heat resistance, and oil resistance, and is particularly suitable for coloring plastics such as vinyl chloride, polyethylene, polystyrene, and ABS resin.
実施例 ４トリクロルベンゼン２０部中にジクロルナフ
タリン−１・ ２ −ジカルボン酸イミド２．７部及び
五塩化リン２．３部の微粉末を分散させ、１２０〜１２
５℃で７０分間撹拌した。Example 4 Fine powder of 2.7 parts of dichloronaphthalene-1,2-dicarboxylic acid imide and 2.3 parts of phosphorus pentachloride was dispersed in 20 parts of trichlorobenzene,
Stirred at 5°C for 70 minutes.
反応の進行と共に混合物は次第に溶解して暗赤色を呈し
た。液温を約１１０℃に冷却し、１．２部の下記２・５
−ジ（ｐ−アミノフエニル）フランを２０部のトリクロ
ルベンゼンに溶解した液を加えると顔料が直ちに析出し
た。As the reaction progressed, the mixture gradually dissolved and took on a dark red color. Cool the liquid temperature to about 110℃, add 1.2 parts of 2.5 below.
When a solution of -di(p-aminophenyl)furan dissolved in 20 parts of trichlorobenzene was added, the pigment immediately precipitated.
同温度で更に３時間反応させた後室温まで冷却、濾過し
、熱メタノールで洗滌、乾燥することにより下記構造式
を有する生成物１．５部を得た。このものは融点３００
℃以上で元素分析結果は下記表の通り計算値とほぼ一致
した。After reacting for an additional 3 hours at the same temperature, the reaction mixture was cooled to room temperature, filtered, washed with hot methanol, and dried to obtain 1.5 parts of a product having the following structural formula. This thing has a melting point of 300
At temperatures above ℃, the elemental analysis results almost agreed with the calculated values as shown in the table below.
この生成物は微粉砕することにより、そのまま着色用顔
料として充分使用可能であるが、更に実施例１と同様の
顔料化を行うことにより一層鮮明な着色力の大きい黄色
顔料微粉末を得た。By finely pulverizing this product, it can be fully used as a coloring pigment as it is, but by further converting it into a pigment in the same manner as in Example 1, a yellow pigment fine powder with even more vivid coloring power was obtained.
本顔料は大きな着色力を有し、又耐熱性、耐光性、耐薬
品性に優れており、塗料、印刷インキ及びプラスチツク
の着色に適する。This pigment has great coloring power and excellent heat resistance, light resistance, and chemical resistance, making it suitable for coloring paints, printing inks, and plastics.
なお、実施例１〜４において製造した本発明顔料の、ジ
メチルホルムアミド（ＤＭＦ）中の最大吸収波長λＭａ
ｘを第１表に示す。In addition, the maximum absorption wavelength λMa in dimethylformamide (DMF) of the pigments of the present invention produced in Examples 1 to 4
x is shown in Table 1.
Claims (1)
、Ｘはハロゲン原子を示し、ｎは０〜２の数を示す。 ）で表わされるナフタリン−１・２−ジカルボン酸イミ
ド類を、不活性溶媒の存在下でハロゲン化処理し、次い
で芳香族ジアミン類と縮合させること▲数式、化学式、
表等があります▼……〔II〕 （式中、Ｒはフェニレン基、ジフェニル基又はジフェニ
ルフラン基を示し、Ｘはハロゲン原子を示し、ｎは０〜
２の数を示す。 ）で表わされるナフタリン−１・２−型ビスアゾメチン
系顔料の製法。[Claims] 1 Naphthalene represented by the general formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼... [I] (wherein, X represents a halogen atom, and n represents a number from 0 to 2) - Halogenating 1,2-dicarboxylic acid imides in the presence of an inert solvent and then condensing them with aromatic diamines ▲Mathematical formula, chemical formula,
There are tables, etc.▼...[II] (In the formula, R represents a phenylene group, diphenyl group, or diphenylfuran group, X represents a halogen atom, and n is 0 to
Indicates the number 2. ) A method for producing a naphthalene-1/2-type bisazomethine pigment.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10697072A JPS5917742B2 (en) | 1972-10-25 | 1972-10-25 | Manufacturing method of bisazomethine pigments |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10697072A JPS5917742B2 (en) | 1972-10-25 | 1972-10-25 | Manufacturing method of bisazomethine pigments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS4964628A JPS4964628A (en) | 1974-06-22 |
| JPS5917742B2 true JPS5917742B2 (en) | 1984-04-23 |
Family
ID=14447151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10697072A Expired JPS5917742B2 (en) | 1972-10-25 | 1972-10-25 | Manufacturing method of bisazomethine pigments |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5917742B2 (en) |
-
1972
- 1972-10-25 JP JP10697072A patent/JPS5917742B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4964628A (en) | 1974-06-22 |
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