JPS6215101B2 - - Google Patents
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- Publication number
- JPS6215101B2 JPS6215101B2 JP54120088A JP12008879A JPS6215101B2 JP S6215101 B2 JPS6215101 B2 JP S6215101B2 JP 54120088 A JP54120088 A JP 54120088A JP 12008879 A JP12008879 A JP 12008879A JP S6215101 B2 JPS6215101 B2 JP S6215101B2
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- formula
- general formula
- compound
- compound represented
- 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
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- 239000000049 pigment Substances 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 17
- 239000003086 colorant Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- LOZJNNNVLREXGU-UHFFFAOYSA-N 3-amino-4,5,6,7-tetrachloroisoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(N)=NC2=O LOZJNNNVLREXGU-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- -1 diisocyanate compound Chemical class 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 238000012916 structural analysis Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- ACSWGYKGNBALHO-UHFFFAOYSA-N 1,3-diisocyanato-5-methoxybenzene Chemical compound COC1=CC(N=C=O)=CC(N=C=O)=C1 ACSWGYKGNBALHO-UHFFFAOYSA-N 0.000 description 2
- BQHPNDYUVBBCQF-UHFFFAOYSA-N 1,3-diisocyanato-5-methylbenzene Chemical compound CC1=CC(N=C=O)=CC(N=C=O)=C1 BQHPNDYUVBBCQF-UHFFFAOYSA-N 0.000 description 2
- NKUPNMVWJRKROM-UHFFFAOYSA-N 1-chloro-3,5-diisocyanatobenzene Chemical compound ClC1=CC(N=C=O)=CC(N=C=O)=C1 NKUPNMVWJRKROM-UHFFFAOYSA-N 0.000 description 2
- OQHXZZGZASQSOB-UHFFFAOYSA-N 3,4,5,6-tetrachlorobenzene-1,2-dicarbonitrile Chemical compound ClC1=C(Cl)C(Cl)=C(C#N)C(C#N)=C1Cl OQHXZZGZASQSOB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000001053 orange pigment Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- YFHCUNVROJHJHV-UHFFFAOYSA-N BrC=1C=C(C=C(C=1)N=C=O)N=C=O Chemical compound BrC=1C=C(C=C(C=1)N=C=O)N=C=O YFHCUNVROJHJHV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 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
- 239000004202 carbamide Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- NIEHEMAZEULEKB-UHFFFAOYSA-N ortho-ethylanisole Natural products CCC1=CC=CC=C1OC NIEHEMAZEULEKB-UHFFFAOYSA-N 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Paints Or Removers (AREA)
Description
【発明の詳細な説明】
本発明は、一般式（）
（式中、Ｒはハロゲン原子、低級アルキル基また
は低級アルコキシ基を表わす）
で示される新規なアゾメチン顔料に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the general formula () (In the formula, R represents a halogen atom, a lower alkyl group, or a lower alkoxy group.) The present invention relates to a novel azomethine pigment represented by the following formula.
一般式（）で示される化合物は新規化合物で
あり、式中の置換基Ｒの種類に応じて、種々の色
を呈する有用な顔料となる。たとえば、後述する
実施例に示されるように、Ｒとして塩素原子、メ
チル基またはメトキシ基を有する場合は、それぞ
れ非常に鮮明な黄色、橙色、橙色を呈する顔料と
なる。 The compound represented by the general formula () is a new compound, and becomes a useful pigment that exhibits various colors depending on the type of substituent R in the formula. For example, as shown in the examples below, when R has a chlorine atom, a methyl group, or a methoxy group, the pigments exhibit very vivid yellow, orange, and orange colors, respectively.
一般式（）で示される化合物は、たとえば式
（）
で示される３―イミノ―４，５，６，７―テトラ
クロロイソインドリン―１―オン２モルに対し
て、一般式（）
（式中、Ｒは一般式（）と同じ意味を表わす）
で示されるジイソシアネート化合物１モルとを不
活性反応溶媒中で反応させることにより得られ
る。 A compound represented by the general formula () is, for example, a compound represented by the formula () For 2 moles of 3-imino-4,5,6,7-tetrachloroisoindolin-1-one represented by the general formula () (In the formula, R represents the same meaning as the general formula ()) It is obtained by reacting 1 mol of a diisocyanate compound represented by the following in an inert reaction solvent.
式（）で示される３―イミノ―４，５，６，
７―テトラクロロイソインドリン―１―オンはテ
トラクロロフタロニトリルをアセトン―水混合溶
媒中で、アンモニアおよび過酸化水素を触媒とし
て加水分解することにより得られる。また、上記
テトラクロロフタロニトリルは、たとえば特公昭
36−5716号公報に記載された方法により、フタロ
ニトリルを、活性炭を触媒として気相塩素化反応
させることによつて得られる。 3-imino-4,5,6, represented by the formula ()
7-Tetrachloroisoindolin-1-one can be obtained by hydrolyzing tetrachlorophthalonitrile in an acetone-water mixed solvent using ammonia and hydrogen peroxide as catalysts. In addition, the above-mentioned tetrachlorophthalonitrile is, for example,
According to the method described in Japanese Patent No. 36-5716, phthalonitrile is obtained by subjecting it to a gas phase chlorination reaction using activated carbon as a catalyst.
一般式（）で示されるジイソシアネート化合
物は、式中Ｒの種類によつて種々のものが考えら
れ、このＲがそのまゝ一般式（）で示される化
合物のＲとして合成される。該ジイソシアネート
化合物の具体例としては、たとえば３，５―ジイ
ソシアナトクロロベンゼン（Ｒ：塩素）、３，５
―ジイソシアナトトルエン（Ｒ：メチル基）、
３，５―ジイソシアナトアニソール（Ｒ：メトキ
シ基）、３，５―ジイソシアナトブロモベンゼン
（Ｒ：臭素）、３，５―ジイソシアナトエチルベン
ゼン（Ｒ：エチル基）、３，５―ジイソシナアト
―１―エトキシベンゼン（Ｒ：エトキシ基）など
が挙げられる。 Various diisocyanate compounds represented by the general formula () can be considered depending on the type of R in the formula, and this R is directly synthesized as R of the compound represented by the general formula (). Specific examples of the diisocyanate compound include 3,5-diisocyanatochlorobenzene (R: chlorine), 3,5
-diisocyanatotoluene (R: methyl group),
3,5-diisocyanatoanisole (R: methoxy group), 3,5-diisocyanatobromobenzene (R: bromine), 3,5-diisocyanatoethylbenzene (R: ethyl group), 3,5-diisocyanato -1-ethoxybenzene (R: ethoxy group) and the like.
一般式（）で示される化合物を製造する反応
は、不活性溶媒中で行なわれるが、使用すること
のできる反応溶媒としては、たとえばクロロベン
ゼン、０―ジクロロベンゼン、ニトロベンゼン、
ベンゼン、トルエン、ジオキサン、アセトニトリ
ル、ジブチルエーテル、メチルエチルケトン、ア
ニソールなどが挙げられる。該反応溶媒は、反応
を物理的に良好に実施できる程度の量を用いるの
がよく、通常、原料として用いる３―イミノ―
４，５，６，７―テトラクロロイソインドリン―
１―オンの５〜30重量倍の量が好適である。 The reaction for producing the compound represented by the general formula () is carried out in an inert solvent, and examples of reaction solvents that can be used include chlorobenzene, 0-dichlorobenzene, nitrobenzene,
Examples include benzene, toluene, dioxane, acetonitrile, dibutyl ether, methyl ethyl ketone, anisole, and the like. The reaction solvent is preferably used in an amount that allows the reaction to be carried out physically well, and usually the 3-imino-
4,5,6,7-tetrachloroisoindoline-
A suitable amount is 5 to 30 times the weight of 1-one.
反応温度は、用いる原料化合物の反応性に応じ
て、種々の温度を適用すべきであるが、通常50〜
250℃の範囲が好ましい。 Various reaction temperatures should be applied depending on the reactivity of the raw material compounds used, but usually 50 to 50°C.
A range of 250°C is preferred.
このようにして得られる一般式（）で示され
る化合物は、そのまゝの状態でも顔料として十分
使用することができるが、さらに粉砕あるいは摩
砕を行なうことにより、着色力等の顔料性能を著
しく向上させることができる。 The compound represented by the general formula () obtained in this way can be used satisfactorily as a pigment as it is, but by further crushing or grinding, the pigment performance such as coloring power can be significantly reduced. can be improved.
本発明の顔料は、耐候性、耐熱性、耐溶剤性、
耐酸性、耐アルカリ性等の顔料物性が極めてすぐ
れており、また彩度、着色力、隠ペイ力等の顔料
性等も極めてすぐれている。したがつて、塗料、
ラツカー、印刷インキ等の着色剤に、またポリエ
ステル類、ポリアミド類、ポリオレフイン類等の
合成樹脂の着色剤として好ましく使用することが
できる。 The pigment of the present invention has weather resistance, heat resistance, solvent resistance,
It has extremely excellent pigment physical properties such as acid resistance and alkali resistance, and also extremely excellent pigment properties such as chroma, coloring power, and hiding power. Therefore, paint,
It can be preferably used as a coloring agent for lacquers, printing inks, etc., and as a coloring agent for synthetic resins such as polyesters, polyamides, polyolefins, etc.
本発明の化合物は、その赤外線吸収スペクトル
が1510cm-1および1670cm-1付近において尿素結合
に由来する特性吸収を示すこと、および核磁気共
鳴スペクトルによる構造解析により、同定するこ
とができる。 The compound of the present invention can be identified by its infrared absorption spectrum showing characteristic absorption derived from urea bonds around 1510 cm -1 and 1670 cm -1 and by structural analysis using nuclear magnetic resonance spectroscopy.
以下、実施例を挙げて説明する。 Examples will be described below.
実施例 １
３―イミノ―４，５，６，７―テトラクロロイ
ソインドリン―１―オン10.0ｇおよび３，５―ジ
イソシアナトクロロベンゼン3.42ｇと、さらに不
活性溶媒として０―ジクロロベンゼン200ｇをフ
ラスコに入れ、120℃で６時間反応させた。次い
で反応液を過し、固型物をＮ，Ｎ―ジメチルホ
ルムアミド、アセトンおよび水で洗浄したのち、
120℃で乾燥し、黄色の顔料12.1ｇを得た（収率
90％）。Example 1 10.0 g of 3-imino-4,5,6,7-tetrachloroisoindolin-1-one and 3.42 g of 3,5-diisocyanatochlorobenzene were added to a flask, as well as 200 g of 0-dichlorobenzene as an inert solvent. and reacted at 120°C for 6 hours. Next, the reaction solution was filtered, and the solid material was washed with N,N-dimethylformamide, acetone, and water.
Drying at 120°C yielded 12.1g of yellow pigment (yield
90%).
この顔料は、赤外線吸収スペクトルおよび核磁
気共鳴スペクトルによる構造解析、および元素分
析値より、次記の構造式で示される化合物である
ことがわかつた。 Structural analysis using infrared absorption spectroscopy and nuclear magnetic resonance spectroscopy, and elemental analysis revealed that this pigment was a compound represented by the following structural formula.
この化合物の赤外線吸収スペクトルを図面に示
す。測定に用いた装置は、日本分光（株）製IR
―Ｇ型赤外分光光度計である。また測定法はKBr
法を使用した。 The infrared absorption spectrum of this compound is shown in the drawing. The equipment used for the measurement was an IR manufactured by JASCO Corporation.
-It is a G-type infrared spectrophotometer. The measurement method is KBr
method was used.
次にこの化合物の元素分析値を示す。 Next, the elemental analysis values of this compound are shown.
Ｃ Ｈ Ｎ Ｏ Cl
計算値（％） 37.8 0.9 11.8 8.4 41.9
実測値（％） 38.5 0.9 10.8 8.2 41.6
この顔料は、耐溶剤性、耐薬品性、耐候性およ
び着色力が優れており、非常に鮮明な黄色を呈す
る。また公知の方法により着色剤として、塗料あ
るいは印刷インキに使用することができる。さら
に、このようにして着色された着色物は、非常に
優れた耐候性、耐熱性、耐マイグレーシヨン性を
有している。 C H N O Cl Calculated value (%) 37.8 0.9 11.8 8.4 41.9 Actual value (%) 38.5 0.9 10.8 8.2 41.6 This pigment has excellent solvent resistance, chemical resistance, weather resistance, and coloring power, and is very vivid. It exhibits a bright yellow color. It can also be used as a coloring agent in paints or printing inks by known methods. Furthermore, the colored product colored in this manner has extremely excellent weather resistance, heat resistance, and migration resistance.
実施例 ２
３―イミノ―４，５，６，７―テトラクロロイ
ソインドリン―１―オン10.0ｇおよび３，５―ジ
イソシアナトトルエン30.6ｇと、さらに不活性溶
媒として０―ジクロロベンゼン200ｇをフラスコ
に入れ、100℃で６時間反応させた。反応生成物
を実施例１と同様に処理し、橙色の顔料が11.9ｇ
得られた（収率91％）。Example 2 10.0 g of 3-imino-4,5,6,7-tetrachloroisoindolin-1-one and 30.6 g of 3,5-diisocyanatotoluene were added to a flask, as well as 200 g of 0-dichlorobenzene as an inert solvent. and reacted at 100°C for 6 hours. The reaction product was treated as in Example 1, yielding 11.9 g of orange pigment.
(yield 91%).
この顔料を実施例１と同様の方法で構造解析し
た結果、下記の構造式で示される化合物であるこ
とがわかつた。 As a result of structural analysis of this pigment in the same manner as in Example 1, it was found to be a compound represented by the following structural formula.
次にこの化合物の元素分析値を示す。 Next, the elemental analysis values of this compound are shown.
Ｃ Ｈ Ｎ Ｏ Cl
計算値（％） 40.4 1.3 11.3 8.6 38.3
実測値（％） 40.4 1.4 11.3 8.8 38.1
この顔料は、非場に鮮明な橙色を呈し、実施例
１の顔料と同等の顔料性能および物性を有してい
る。 C H N O Cl Calculated value (%) 40.4 1.3 11.3 8.6 38.3 Actual value (%) 40.4 1.4 11.3 8.8 38.1 This pigment exhibits a vivid orange color outside of the field, and has the same pigment performance and physical properties as the pigment of Example 1. have.
実施例 ３
３―イミノ―４，５，６，７―テトラクロロイ
ソインドリン―１―オン10.0ｇおよび３，５―ジ
イソシアナトアニソール3.35ｇと、さらに不活性
溶媒として０―ジクロロベンゼン200ｇをフラス
コに入れ、100℃で６時間反応させた。反応生成
物を実施例１と同様に処理し、橙色の顔料12.7ｇ
（収率95％）を得た。Example 3 In a flask were added 10.0 g of 3-imino-4,5,6,7-tetrachloroisoindolin-1-one and 3.35 g of 3,5-diisocyanatoanisole, and further 200 g of 0-dichlorobenzene as an inert solvent. and reacted at 100°C for 6 hours. The reaction product was treated as in Example 1, yielding 12.7 g of orange pigment.
(yield 95%).
この顔料を実施例１と同様の方法で構造解析し
た結果、下記の構造式で示される化合物であるこ
とがわかつた。 As a result of structural analysis of this pigment in the same manner as in Example 1, it was found to be a compound represented by the following structural formula.
次にこの化合物の元素分析値を示す。 Next, the elemental analysis values of this compound are shown.
Ｃ Ｈ Ｎ Ｏ Cl
計算値（％） 39.6 1.3 11.1 10.6 37.5
実測値（％） 39.6 1.4 11.0 10.7 37.3
この顔料は、非常に鮮明な橙色を呈し、実施例
１の顔料と同等の顔料性能および物性を有してい
る。 C H N O Cl Calculated value (%) 39.6 1.3 11.1 10.6 37.5 Actual value (%) 39.6 1.4 11.0 10.7 37.3 This pigment exhibits a very bright orange color and has the same pigment performance and physical properties as the pigment of Example 1. have.
図面は実施例１の化合物の赤外線吸収スペクト
ルを示す。
The figure shows the infrared absorption spectrum of the compound of Example 1.
Claims (1)
は低級アルコキシ基を表わす） で示されるアゾメチン顔料。 ２ Ｒが塩素原子である特許請求の範囲第１項記
載のアゾメチン顔料。 ３ Ｒがメチル基である特許請求の範囲第１項記
載のアゾメチン顔料。 ４ Ｒがメトキシ基である特許請求の範囲第１項
記載のアゾメチン顔料。[Claims] 1. General formula (In the formula, R represents a halogen atom, a lower alkyl group, or a lower alkoxy group.) An azomethine pigment represented by the following formula. 2. The azomethine pigment according to claim 1, wherein R is a chlorine atom. 3. The azomethine pigment according to claim 1, wherein R is a methyl group. 4. The azomethine pigment according to claim 1, wherein R is a methoxy group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12008879A JPS5645958A (en) | 1979-09-20 | 1979-09-20 | New azomethine pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12008879A JPS5645958A (en) | 1979-09-20 | 1979-09-20 | New azomethine pigment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5645958A JPS5645958A (en) | 1981-04-25 |
| JPS6215101B2 true JPS6215101B2 (en) | 1987-04-06 |
Family
ID=14777605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12008879A Granted JPS5645958A (en) | 1979-09-20 | 1979-09-20 | New azomethine pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5645958A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55152749A (en) * | 1979-05-16 | 1980-11-28 | Asahi Chem Ind Co Ltd | Novel organic compound and preparation thereof |
-
1979
- 1979-09-20 JP JP12008879A patent/JPS5645958A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55152749A (en) * | 1979-05-16 | 1980-11-28 | Asahi Chem Ind Co Ltd | Novel organic compound and preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5645958A (en) | 1981-04-25 |
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