JP2003082253A - Disazo dye, method for producing the same and printing ink composition - Google Patents
Disazo dye, method for producing the same and printing ink compositionInfo
- Publication number
- JP2003082253A JP2003082253A JP2001280885A JP2001280885A JP2003082253A JP 2003082253 A JP2003082253 A JP 2003082253A JP 2001280885 A JP2001280885 A JP 2001280885A JP 2001280885 A JP2001280885 A JP 2001280885A JP 2003082253 A JP2003082253 A JP 2003082253A
- Authority
- JP
- Japan
- Prior art keywords
- acetoacetanilide
- group
- parts
- solution
- disazo pigment
- 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
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明はジスアゾ顔料に関
し、詳細には従来のジスアゾ顔料に比較して短時間でフ
ラッシングが可能であり、得られた印刷インキの透明
性、流動性に優れたジスアゾ顔料、およびこれを配合し
た印刷インキに関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a disazo pigment, and more specifically, it is possible to perform flushing in a shorter time than conventional disazo pigments, and the resulting printing ink is excellent in transparency and fluidity. , And a printing ink containing the same.
【０００２】[0002]
【従来の技術】従来、プロセスのオフセットインキはウ
ェットケーキをフラッシングしてインキ化する方法とウ
ェットケーキの乾燥物を３本ロール、サンドミル、ショ
ットミルを用いて分散しインキ化する方法に大別される
が大量生産には前者の方法が優れている。2. Description of the Related Art Conventionally, offset inks for processes are roughly classified into a method of flushing a wet cake into an ink and a method of dispersing a wet cake dry matter into a ink by dispersing it with a three-roll, a sand mill and a shot mill. However, the former method is superior for mass production.
【０００３】近年、インキの生産性向上がインキ単価の
低減の中でクローズアップされてきた。生産性の向上の
ためにはウェットケーキをフラッシングする工程での時
間の短縮、及びフラッシング後のインキ中の残存水分を
完全に除去するための減圧・加熱工程での加熱温度の上
昇による時間の短縮が必須条件である。さらにフラッシ
ングする工程での時間の短縮はフラッシングの熱による
品質劣化を防ぐ上でも重要である。In recent years, the improvement of ink productivity has been highlighted in order to reduce the unit price of ink. To improve productivity, shorten the time in the process of flushing the wet cake, and shorten the time by increasing the heating temperature in the depressurization / heating process to completely remove the residual water in the ink after flushing. Is an essential condition. Furthermore, shortening the time in the flushing process is important for preventing quality deterioration due to heat of flushing.
【０００４】しかしながら加熱温度の上昇は品質面で透
明性、濃度の著しい劣化の原因になる。従って現実的な
対応としてインキ化時の熱による劣化を考慮してウェッ
トケーキをより透明で高濃度にしなくてはならない。However, an increase in heating temperature causes a remarkable deterioration in transparency and density in terms of quality. Therefore, as a practical measure, it is necessary to make the wet cake more transparent and have a high concentration in consideration of deterioration due to heat when the ink is formed.
【０００５】ジスアゾ顔料の透明性、濃度を向上させる
方法として、特公昭５５−１０６３０号公報には、２つ
のカップリング成分すなわちアセトアセトアニリドとそ
の極性基含有アセトアセトアニリドとの混合カップリン
グが開示されている。この方法によれば、透明性、濃度
に優れた黄インキを製造することができるが、極性基を
有するカップリング成分を使用したために顔料表面が親
水性になってしまいフラッシングする工程での時間の短
縮には不利である。As a method for improving the transparency and the concentration of the disazo pigment, Japanese Patent Publication No. 55-10630 discloses a mixed coupling of two coupling components, that is, acetoacetanilide and its polar group-containing acetoacetanilide. There is. According to this method, it is possible to produce a yellow ink excellent in transparency and concentration, but since the coupling component having a polar group is used, the pigment surface becomes hydrophilic and the time required for the flushing process is reduced. There is a disadvantage in shortening.
【０００６】また特開昭６３−７２７６２号公報、特開
昭６３−１７８１６９号公報及び特開２０００−７９３
１号公報等には、非対称型ジスアゾ顔料化合物を同一反
応容器中で効率良く、対称型よりも多くの割合で製造す
る方法が示されている。この方法によれば、極性のカッ
プリング成分と非極性のカップリング成分を用いること
により、従来のジスアゾ顔料より透明で流動性に優れた
顔料がえられるが、極性のカップリング成分を多量に含
有するためフラッシング工程での時間の短縮には不利で
ある。さらに極性のカップリング成分は汎用で商業ベー
スで使用されている非極性のカップリング成分と比較し
て高価であるため、顔料のコストアップをもたらし、イ
ンキの生産性向上によるインキ単価の低減には逆行す
る。Further, JP-A-63-72762, JP-A-63-178169 and JP-A-2000-793.
Japanese Unexamined Patent Publication (Kokai) No. 1 discloses a method for efficiently producing an asymmetric type disazo pigment compound in the same reaction vessel in a larger proportion than in a symmetrical type. According to this method, by using a polar coupling component and a non-polar coupling component, a pigment that is more transparent and has better fluidity than conventional disazo pigments can be obtained, but it contains a large amount of polar coupling component. Therefore, it is disadvantageous in reducing the time required for the flushing process. Furthermore, since the polar coupling component is more expensive than the non-polar coupling component that is used on a general-purpose and commercial basis, it increases the cost of the pigment and reduces the ink unit price by improving the productivity of the ink. Go backwards.
【０００７】[0007]
【発明が解決しようとする課題】本発明は、従来のジス
アゾ顔料に比較して短時間でフラッシングが完了でき、
さらに透明で且つ流動性に優れた印刷インキを提供する
ことを目的とする。DISCLOSURE OF THE INVENTION The present invention is capable of completing flushing in a short time as compared with a conventional disazo pigment,
Another object is to provide a printing ink that is transparent and has excellent fluidity.
【０００８】[0008]
【発明が解決しようとする課題】すなわち本発明は、
３，３’−ジクロロベンジジンのテトラゾ化物とアセト
アセトアニリド系化合物をカップリングさせてなるジス
アゾ顔料において、該アセトアセトアニリド系化合物
が、アセトアセトアニリド８０〜９９モル％、式（１）
で示される極性基含有アセトアセトアニリド化合物０．
５〜１０モル％および式（２）で示されるアルコキシ基
含有アセトアセトアニリド化合物０．５〜１０モル％か
らなることを特徴とするジスアゾ顔料に関する。That is, the present invention is
In a disazo pigment obtained by coupling a tetrazo compound of 3,3′-dichlorobenzidine and an acetoacetanilide compound, the acetoacetanilide compound is 80 to 99 mol% of acetoacetanilide, and is represented by the formula (1).
A polar group-containing acetoacetanilide compound represented by
It relates to a disazo pigment comprising 5 to 10 mol% and an alkoxy group-containing acetoacetanilide compound represented by the formula (2) 0.5 to 10 mol%.
【０００９】式（１）
ＣＨ3ＣＯＣＨ2ＣＯＮＨ−Ｘ
（式中、Ｘはカルボン酸基、スルホン酸基およびこれら
の金属塩からなる群から選ばれる同一又は異なる１〜４
個の置換基を有するフェニル基（該フェニル基は、置換
可能な位置がメチル基、メトキシ基、水酸基または塩素
原子で置換されていてもよい。）を示す。）
式（２）
ＣＨ3ＣＯＣＨ2ＣＯＮＨ−Ｙ
（式中、Ｙは炭素数２〜４のアルコキシ基（該フェニル
基は、置換可能な位置がメチル基、メトキシ、水酸基ま
たは塩素原子で置換されていてもよい。）を示す。）
更に本発明は、アセトアセトアニリド、極性基含有アセ
トアセトアニリド化合物およびアルコキシ基含有アセト
アセトアニリド化合物の混合物と３，３’−ジクロロベ
ンジジンのテトラゾ液とを反応させることを特徴とする
上記ジスアゾ顔料の製造方法に関する。Formula (1) CH 3 COCH 2 CONH-X (wherein X is the same or different 1 to 4 selected from the group consisting of a carboxylic acid group, a sulfonic acid group and metal salts thereof.
Shows a phenyl group having 4 substituents (the phenyl group may be substituted at a substitutable position with a methyl group, a methoxy group, a hydroxyl group or a chlorine atom). ) Formula (2) CH 3 COCH 2 CONH -Y ( wherein, Y is an alkoxy group (the phenyl group of 2 to 4 carbon atoms, substitutable position is a methyl group, methoxy, optionally substituted by a hydroxyl group or a chlorine atom Further, the present invention is characterized by reacting a mixture of acetoacetanilide, a polar group-containing acetoacetanilide compound and an alkoxy group-containing acetoacetanilide compound with a tetrazo solution of 3,3′-dichlorobenzidine. And a method for producing the above-mentioned disazo pigment.
【００１０】更に本発明は、同一容器内で、アセトアセ
トアニリドおよび極性基含有アセトアセトアニリド化合
物の混合物と３，３’−ジクロロベンジジンのテトラゾ
液とを予め反応させた後、アルコキシ基含有アセトアセ
トアニリド化合物と３，３’−ジクロロベンジジンのテ
トラゾ液とを反応させることを特徴とする上記ジスアゾ
顔料の製造方法に関する。Further, in the present invention, a mixture of acetoacetanilide and a polar group-containing acetoacetanilide compound is preliminarily reacted with a tetrazo solution of 3,3'-dichlorobenzidine in the same container, and then an alkoxy group-containing acetoacetanilide compound is added. The present invention relates to a method for producing the above-mentioned disazo pigment, which comprises reacting with a tetrazo solution of 3,3'-dichlorobenzidine.
【００１１】更に本発明は、同一容器内で、アセトアセ
トアニリドおよび極性基含有アセトアセトアニリド化合
物の混合物と３，３’−ジクロロベンジジンのテトラゾ
液とを予め反応させた後、アセトアセトアニリドおよび
アルコキシ基含有アセトアセトアニリド化合物の混合物
と３，３’−ジクロロベンジジンのテトラゾ液とを反応
させることを特徴とする上記ジスアゾ顔料の製造方法に
関する。Further, in the present invention, a mixture of acetoacetanilide and a polar group-containing acetoacetanilide compound is preliminarily reacted with a tetrazo solution of 3,3'-dichlorobenzidine in the same container, and then acetoacetanilide and an alkoxy group-containing acetoanilide are prepared. The present invention relates to a method for producing a disazo pigment, which comprises reacting a mixture of acetanilide compounds with a tetrazo solution of 3,3'-dichlorobenzidine.
【００１２】更に本発明は、反応が、弱酸性の緩衝溶液
中に３，３’−ジクロロベンジジンのテトラゾ溶液とア
セトアセトアニリド系化合物のアルカリ性溶液とを連続
的に添加する方法で行われる上記ジスアゾ顔料の製造方
法に関する。The present invention further provides the above disazo pigment, wherein the reaction is carried out by continuously adding a tetrazo solution of 3,3'-dichlorobenzidine and an alkaline solution of an acetoacetanilide compound to a weakly acidic buffer solution. Manufacturing method.
【００１３】更に本発明は、上記ジスアゾ顔料がウェッ
トケーキ状態で印刷インキビヒクルによりフラッシング
されることを特徴とする印刷インキの製造方法に関す
る。Further, the present invention relates to a method for producing a printing ink, wherein the disazo pigment is flushed with a printing ink vehicle in a wet cake state.
【００１４】更に本発明は、上記ジスアゾ顔料と印刷イ
ンキビヒクルとからなることを特徴とする印刷インキに
関する。Furthermore, the present invention relates to a printing ink comprising the above-mentioned disazo pigment and a printing ink vehicle.
【００１５】式（１）で示される極性基含有アセトアセ
トアニリド化合物の具体例としては、カルボン酸基を持
つものとして２−アセトアセチルアミノ安息香酸、４−
アセトアセチルアミノ安息香酸、４−アセトアセチルア
ミノ−２−クロロ安息香酸、４−アセトアセチルアミノ
−２ーメチル安息香酸、４−アセアセチルアミノ−２−
安息香酸、５−アセトアセチルアミノ−２−ヒドロキシ
安息香酸等が、またスルホン酸基としては４−アセトア
セチルアミノベンゼンスルホン酸等がある。Specific examples of the polar group-containing acetoacetanilide compound represented by the formula (1) include 2-acetoacetylaminobenzoic acid having a carboxylic acid group, 4-
Acetoacetylaminobenzoic acid, 4-acetoacetylamino-2-chlorobenzoic acid, 4-acetoacetylamino-2-methylbenzoic acid, 4-aceacetylamino-2-
Benzoic acid, 5-acetoacetylamino-2-hydroxybenzoic acid and the like, and sulfonic acid groups include 4-acetoacetylaminobenzenesulfonic acid and the like.
【００１６】これらの極性基含有アセトアセトアニリド
における極性基の金属塩を構成する金属としては、ナト
リウム、カリウム、カルシウム、バリウム、ストロンチ
ウム、マンガン、亜鉛、マグネシウム、アルミニウム等
がある。Metals constituting the polar group metal salt of these polar group-containing acetoacetanilides include sodium, potassium, calcium, barium, strontium, manganese, zinc, magnesium and aluminum.
【００１７】式（２）で示されるアルコキシ基含有アセ
トアセトアニリド化合物のアルコキシ基は、エトキシ
基、ｎ−プロポキシ基およびその異性体、ｎ−ブトキシ
基およびその異性体等であって、具体例としては、アセ
トアセト−２−フェネチジド、アセトアセト−４−フェ
ネチジド、アセトアセト−２−ヒドロキシ−４−フェネ
チジド、 アセトアセト−２−メチル−４−フェネチジ
ド、アセトアセト−２−クロロ−４−フェネチジド、ア
セトアセト−２−メトキシ−４−フェネチジド、アセト
アセト−４−プロポキシアニリド、アセトアセト−３−
イソプロポキシアニリド、アセトアセト−４−ブトキシ
アニリドがある。The alkoxy group of the acetoacetanilide compound containing an alkoxy group represented by the formula (2) is an ethoxy group, an n-propoxy group and its isomer, an n-butoxy group and its isomer, and the like. , Acetoaceto-2-phenetidide, acetoaceto-4-phenetidide, acetoaceto-2-hydroxy-4-phenetidide, acetoaceto-2-methyl-4-phenetidide, acetoaceto-2-chloro-4-phenetidide, acetoaceto-2-methoxy-4 -Phenethide, acetoaceto-4-propoxyanilide, acetoacet-3-
There are isopropoxyanilide and acetoaceto-4-butoxyanilide.
【００１８】本発明のジスアゾ顔料におけるアセトアセ
トアニリド系化合物成分相互の割合は、アセトアセトア
ニリドが９９〜８０モル％、極性基含有アセトアセトア
ニリド化合物が１０〜０．５モル％、好ましくは１〜５
モル％、アルコキシ基含有アセトアセトアニリド化合物
が１０．０〜０．５モル％、好ましくは１〜５モル％で
ある。極性基含有アセトアセトアニリド化合物の配合量
の下限値は、透明性と濃度により制限を受け、上限値は
フラッシング工程の時間短縮において制限を受ける。ア
ルコキシ基含有アセトアセトアニリド化合物の配合量の
下限値はフラッシング工程の時間短縮において制限を受
け、上限値は透明性過剰による流動性の低下、コストに
おいて制限を受ける。In the disazo pigment of the present invention, the proportion of acetoacetanilide compound components is 99-80 mol% for acetoacetanilide and 10-0.5 mol% for polar group-containing acetoacetanilide compound, preferably 1-5.
Mol%, and the alkoxy group-containing acetoacetanilide compound is 10.0 to 0.5 mol%, preferably 1 to 5 mol%. The lower limit of the blending amount of the polar group-containing acetoacetanilide compound is limited by transparency and concentration, and the upper limit is limited in shortening the flushing process time. The lower limit of the blending amount of the alkoxy group-containing acetoacetanilide compound is limited in shortening the time of the flushing step, and the upper limit is limited in fluidity due to excessive transparency and in cost.
【００１９】本発明において３，３’−ジクロロベンジ
ジンのテトラゾ液とカップリング成分とのカップリング
反応は特に制限されないが、常法により酢酸酸性下、す
なわち、ｐＨ６〜３の範囲、温度１０℃〜３０℃、時間
３０分〜６０分の間で行う方法がある。また、予め酢酸
と苛性ソーダを用いてｐＨを約４．５前後に調整した酸
性緩衝溶液を作製し、カップリング成分を苛性ソーダで
溶解したカップラー溶液とテトラゾ溶液を同時に等しい
反応量で添加する方法であってもよく、この方法によれ
ば、カップリング成分を析出させることなく反応させる
ことができるので好ましい。In the present invention, the coupling reaction between the tetrazo solution of 3,3'-dichlorobenzidine and the coupling component is not particularly limited, but it is carried out by a conventional method under acetic acid acidity, that is, in the range of pH 6 to 3, temperature 10 ° C. There is a method of performing the treatment at 30 ° C. for 30 minutes to 60 minutes. Further, it is a method of preparing an acidic buffer solution in which the pH is adjusted to about 4.5 using acetic acid and caustic soda in advance, and adding the coupler solution in which the coupling component is dissolved in caustic soda and the tetrazo solution at the same reaction amount at the same time. However, this method is preferable because the reaction can be performed without depositing the coupling component.
【００２０】本発明のジスアゾ顔料の製造方法は、アセ
トアセトアニライド系化合物を３成分を混合したものを
３，３’−ジクロロベンジジンのテトラゾ液と反応させ
る方法であってもよいし、アセトアセトアニリドおよび
極性基含有アセトアセトアニリド化合物の混合物と３，
３’−ジクロロベンジジンのテトラゾ液とを最初に反応
させた後、第二段の反応として、アルコキシ基含有アセ
トアセトアニリド化合物と３，３’−ジクロロベンジジ
ンのテトラゾ液とを反応させるか、アセトアセトアニリ
ドおよびアルコキシ基含有アセトアセトアニリド化合物
の混合物と３，３’−ジクロロベンジジンのテトラゾ液
とを反応させる方法であってもい。このような二段階の
カップリング工程とすることにより、ジスアゾ顔料粒子
の表面に疎水性のアルコキシル基含有ジスアゾ化合物が
多く生成するので、透明性、流動性を損なうことなくフ
ラッシング工程の時間が短縮化されたジスアゾ顔料が得
られる。The method for producing the disazo pigment of the present invention may be a method of reacting a mixture of three components of an acetoacetanilide compound with a tetrazo solution of 3,3'-dichlorobenzidine, or acetoacetanilide. And a mixture of polar group-containing acetoacetanilide compounds and 3,
After first reacting with 3'-dichlorobenzidine tetrazo solution, as a second step reaction, an alkoxy group-containing acetoacetanilide compound is reacted with 3,3'-dichlorobenzidine tetrazo solution, or acetoacetanilide and A method of reacting a mixture of alkoxy group-containing acetoacetanilide compounds with a tetrazo solution of 3,3′-dichlorobenzidine may be used. By such a two-step coupling process, a large amount of hydrophobic alkoxyl group-containing disazo compound is generated on the surface of the disazo pigment particles, so that the flushing process time can be shortened without impairing transparency and fluidity. The disazo pigment obtained is obtained.
【００２１】又、本発明のジスアゾ顔料は、アセトアセ
トアニリドおよび極性基含有アセトアセトアニリド化合
物の混合物と３，３’−ジクロロベンジジンのテトラゾ
化物とから得られるジスアゾ顔料と、アセトアセトアニ
ライドライドおよびアルコキシ基含有アセトアセトアニ
リド化合物の混合物と３，３’−ジクロロベンジジンの
テトラゾ化物とから得られるジスアゾ顔料との混合した
ものであってもよい。Further, the disazo pigment of the present invention comprises a disazo pigment obtained from a mixture of acetoacetanilide and a polar group-containing acetoacetanilide compound and a tetrazodide of 3,3'-dichlorobenzidine, an acetoacetanilide and an alkoxy group. It may be a mixture of a mixture of contained acetoacetanilide compounds and a disazo pigment obtained from a tetrazo compound of 3,3′-dichlorobenzidine.
【００２２】本発明により得られたジスアゾ顔料の水ス
ラリーはｐＨ９〜１４のアルカリ側に調整後、ロジンの
アルカリ塩溶液（添加量は顔料に対して３〜１０重量
％）、顔料スラリーを撹拌し均一化し、塩酸を加えてｐ
Ｈ６〜４程度の酸性にして顔料表面にロジンを析出さ
せ、その後９０℃まで加熱し、３０分保持してから、濾
過、水洗、顔料分２８〜３２％になるように圧搾するこ
とによってフラッシング工程に供するジスアゾ顔料のウ
ェットケーキが得られる。The water slurry of the disazo pigment obtained by the present invention is adjusted to the alkali side having a pH of 9 to 14, and then the rosin alkali salt solution (the addition amount is 3 to 10% by weight with respect to the pigment) is stirred. Homogenize, add hydrochloric acid and p
A rosin is precipitated on the surface of the pigment by acidifying it to about H6 to 4 and then heating to 90 ° C., holding for 30 minutes, filtering, washing with water, and squeezing to a pigment content of 28 to 32% to perform a flushing step. A wet cake of disazo pigment to be used in the above is obtained.
【００２３】フラッシングは顔料のウェットケーキ８０
重量部（乾燥換算）に対してオフセット用印刷インキビ
ヒクル１８０〜２２０重量部を添加しフラッシャーを用
いて行われる。Flushing is pigment wet cake 80
180 to 220 parts by weight of the offset printing ink vehicle is added to parts by weight (dry basis), and the addition is performed using a flasher.
【００２４】本発明のジスアゾ顔料はプロセス用オフセ
ットインキとして使用される。オフセットインキの組成
物は本発明のジスアゾ顔料３〜３５重量％とオフセット
用インキビヒクル９７〜４５重量％、その他補助剤（ド
ライヤー、レベリング改良剤、増粘剤）や体質顔料０〜
２０重量％からなる。オフセット用インキビヒクルはロ
ジン変性フェノール樹脂、石油樹脂、アルキッド樹脂、
またはこれらの乾性油変性樹脂等の樹脂２０〜５０重量
％、アマニ油、桐油、大豆油等の植物油０〜３０重量
％、ｎ−パラフィン、イソパラフィン、α−オレフィン
等の溶剤１０〜６０重量％からなるものである。The disazo pigment of the present invention is used as a process offset ink. The composition of the offset ink is 3 to 35% by weight of the disazo pigment of the present invention, 97 to 45% by weight of the offset ink vehicle, other auxiliary agents (dryer, leveling improver, thickener) and extender pigment 0 to.
It consists of 20% by weight. The ink vehicle for offset is rosin-modified phenol resin, petroleum resin, alkyd resin,
Alternatively, from 20 to 50% by weight of a resin such as a dry oil-modified resin, 0 to 30% by weight of a vegetable oil such as linseed oil, tung oil, soybean oil, and 10 to 60% by weight of a solvent such as n-paraffin, isoparaffin, and α-olefin. It will be.
【００２５】[0025]
【実施例】以下実施例をあげて本発明を具体的に説明す
る。実施例において「部」は全て重量部を示す。EXAMPLES The present invention will be specifically described with reference to the following examples. In the examples, all "parts" indicate parts by weight.
【００２６】[0026]
【実施例１】水４００部に３，３’−ジクロロベンジジ
ン２５．３部と３５％塩酸１６．５部を加えた。この溶
液を０℃に冷却後２０％亜硝酸ソーダ溶液を７０部加
え、１時間撹拌した。少量のスルファミン酸を加え過剰
の亜硝酸ソーダを消失させて、３，３’−ジクロロベン
ジジンのテトラゾ溶液とした。一方、水４００部にアセ
トアセトアニリド３４．０部と５−アセトアセチルアミ
ノ−２−ヒドロキシ安息香酸０．９部とアセトアセト−
４−フェネチジド０．９部及び苛性ソーダ２０部を加え
て溶解した。この溶液に８０％酢酸４５部を少しずつ加
えて懸濁液とし、これに前記テトラゾ溶液を約３０分要
して加えた。この間の反応温度は約１５℃に保持した。
得られたジスアゾ顔料のスラリーを苛性ソーダでｐＨ１
０．５に調整後、ロジンの１０％アルカリ塩溶液を６０
部添加した。このスラリーを１０分間撹拌後、塩酸を加
えてｐＨ５．０に調整して顔料表面にロジンを析出させ
た。その後９０℃まで加熱し、３０分保持してから、濾
過、水洗、圧搾して顔料分３０．０％のウェットケーキ
を得た。Example 1 To 400 parts of water, 25.3 parts of 3,3'-dichlorobenzidine and 16.5 parts of 35% hydrochloric acid were added. After this solution was cooled to 0 ° C., 70 parts of 20% sodium nitrite solution was added and stirred for 1 hour. A small amount of sulfamic acid was added to eliminate excess sodium nitrite to obtain a tetrazo solution of 3,3′-dichlorobenzidine. On the other hand, in 400 parts of water, 34.0 parts of acetoacetanilide, 0.9 part of 5-acetoacetylamino-2-hydroxybenzoic acid and acetoaceto-
0.9 parts of 4-phenetizide and 20 parts of caustic soda were added and dissolved. To this solution, 45 parts of 80% acetic acid was added little by little to form a suspension, and the tetrazo solution was added to this suspension in about 30 minutes. During this period, the reaction temperature was kept at about 15 ° C.
The obtained disazo pigment slurry was adjusted to pH 1 with caustic soda.
After adjusting to 0.5, add 60% rosin 10% alkali salt solution.
Added in parts. After stirring this slurry for 10 minutes, hydrochloric acid was added to adjust the pH to 5.0 to precipitate rosin on the surface of the pigment. Then, the mixture was heated to 90 ° C., kept for 30 minutes, filtered, washed with water, and pressed to obtain a wet cake having a pigment content of 30.0%.
【００２７】フラッシングによるインキ化は１Ｌフラッ
シャーを用いて行った。すなわち上記ウェットケーキを
乾燥重量として８０部と予め１００℃に温めたオフセッ
ト用インキビヒクル１９０部をフラッシャー中に同時に
投入し、フラッシングを行った（オープンフラッシング
工程：トータル時間１５分）。次にフラッシングで出て
きた水を除去後、減圧（１〜８×１０3Ｐａ）及び混練
物の内部温度が１００℃になるまで加熱（熱媒温度１３
０℃） を３０分間行い混練物中の水を完全に除去した
（バキュームフラッシング工程）。この混練物にオフセ
ット用インキビヒクル３９０部と溶剤４４部を徐々に加
えた後フラッシャーから取り出した。その後３本ロール
を用いてロール温度６０℃、１０Ｂａrｒの圧力をかけ
て練肉し粗大粒子を除去し、ベースインキを得た。この
ベースインキ６２部にオフセット用インキビヒクル２５
部、溶剤１０部、補助剤３部加えてタック５．８〜６．
０に調整して最終インキを得た。Ink formation by flushing was performed using a 1 L flasher. That is, 80 parts of the wet cake as a dry weight and 190 parts of the offset ink vehicle preheated to 100 ° C. were simultaneously put into a flasher to perform flushing (open flushing step: total time 15 minutes). Next, after removing the water that came out by flushing, the pressure was reduced (1 to 8 × 10 3 Pa) and heating was performed until the internal temperature of the kneaded material reached 100 ° C. (heating medium temperature 13
0 ° C) Was carried out for 30 minutes to completely remove the water in the kneaded material (vacuum flushing step). To this kneaded material, 390 parts of the offset ink vehicle and 44 parts of the solvent were gradually added and then taken out from the flasher. Then, using three rolls, a roll temperature of 60 ° C. and a pressure of 10 Barr were applied to knead to remove coarse particles to obtain a base ink. The ink vehicle 25 for offset is added to 62 parts of this base ink.
Parts, 10 parts of solvent, 3 parts of auxiliary agent, and tack 5.8 to 6.
The final ink was obtained by adjusting to 0.
【００２８】[0028]
【実施例２】テトラゾ溶液の製造法は実施例１と同様に
行った。一方、水２００部にアセトアセトアニリド３
４．０部と５−アセトアセチルアミノ−２−ヒドロキシ
安息香酸０．９部とアセトアセト−４−フェネチジド
０．９部及び苛性ソーダ１４部を加え溶解したカップラ
ー溶液を作製した。また８０％酢酸２０部、苛性ソーダ
５部のｐＨ４．５に調整した緩衝溶液６００部を作製し
た。この緩衝溶液に、テトラゾ溶液及びカップラー溶液
を同時に、テトラゾが反応中に遊離しないように両溶液
の流速を調整しながら約３０分要して加えた。カップリ
ング反応温度は約１５℃に保持した。得られたジスアゾ
顔料スラリーは実施例１と同様の操作を行い顔料分３
０．０％のウェットケーキを得た。インキ化の方法は実
施例１と同様に行い最終インキを得た。Example 2 The manufacturing method of the tetrazo solution was the same as in Example 1. On the other hand, acetoacetanilide 3 was added to 200 parts of water.
A coupler solution was prepared by adding 4.0 parts, 0.9 parts of 5-acetoacetylamino-2-hydroxybenzoic acid, 0.9 parts of acetoaceto-4-phenetide and 14 parts of caustic soda, and dissolving them. Also, 600 parts of a buffer solution of 20 parts of 80% acetic acid and 5 parts of caustic soda adjusted to pH 4.5 was prepared. The tetrazo solution and the coupler solution were simultaneously added to this buffer solution over about 30 minutes while adjusting the flow rates of both solutions so that tetrazo was not released during the reaction. The coupling reaction temperature was kept at about 15 ° C. The obtained disazo pigment slurry was treated in the same manner as in Example 1 to give a pigment content of 3
A wet cake of 0.0% was obtained. The inking method was the same as in Example 1 to obtain the final ink.
【００２９】[0029]
【実施例３】テトラゾ溶液の製造法は実施例１と同様に
行った。一方、水３５０部にアセトアセトアニリド３
４．０部と５−アセトアセチルアミノ−２−ヒドロキシ
安息香酸０．９部及び苛性ソーダ１９．６部を加えて溶
解した。この溶液に８０％酢酸４５部を少しずつ加えて
懸濁液とし、これに前記テトラゾ溶液を約３０分要して
加えた。この間の反応温度は約１５℃に保持した。得ら
れたジスアゾ顔料のスラリーに、水５０部にアセトアセ
ト−４−フェネチジド０．９部と苛性ソーダ０．４部で
溶解した溶液とテトラゾ溶液を同時に、テトラゾが反応
中に遊離しないように両溶液の流速を調整しながら、約
１０分要して加えた。この間の反応温度も約１５℃に保
持した。 得られたジスアゾ顔料スラリーは実施例１と
同様の操作を行い顔料分３０．０％のウェットケーキを
得た。インキ化の方法は実施例１と同様に行い最終イン
キを得た。Example 3 A tetrazo solution was produced in the same manner as in Example 1. Meanwhile, acetoacetanilide 3 was added to 350 parts of water.
4.0 parts, 0.9 parts of 5-acetoacetylamino-2-hydroxybenzoic acid and 19.6 parts of caustic soda were added and dissolved. To this solution, 45 parts of 80% acetic acid was added little by little to form a suspension, and the tetrazo solution was added to this suspension in about 30 minutes. During this period, the reaction temperature was kept at about 15 ° C. Into the obtained slurry of disazo pigment, a solution prepared by dissolving 0.9 part of acetoaceto-4-phenetidide and 0.4 part of caustic soda in 50 parts of water and a tetrazo solution were simultaneously prepared so that tetrazo was not released during the reaction. It took about 10 minutes to add while adjusting the flow rate. The reaction temperature during this period was also maintained at about 15 ° C. The obtained disazo pigment slurry was treated in the same manner as in Example 1 to obtain a wet cake having a pigment content of 30.0%. The inking method was the same as in Example 1 to obtain the final ink.
【００３０】[0030]
【実施例４】テトラゾ溶液の製造法は実施例１と同様に
行った。一方、水２００部にアセトアセトアニリド１
７．０部と５−アセトアセチルアミノ−２−ヒドロキシ
安息香酸０．９部及び苛性ソーダ１０部を加えて溶解し
た。この溶液に８０％酢酸４５部を少しずつ加えて懸濁
液とし、これに前記テトラゾ溶液を約２０分要して加え
た。この間の反応温度は約１５℃に保持した。得られた
ジスアゾ顔料のスラリーに、水２００部にアセトアセト
アニリド１７．０部とアセトアセト−４−フェネチジド
０．９部及び苛性ソーダ１０部で溶解した溶液とテトラ
ゾ溶液を同時に、テトラゾが反応中に遊離しないように
両溶液の流速を調整しながら、約２０分要して加えた。
この間の反応温度も約１５℃に保持した。 得られたジ
スアゾ顔料スラリーは実施例１と同様の操作を行い顔料
分３０．０％のウェットケーキを得た。インキ化の方法
は実施例１と同様に行い最終インキを得た。Example 4 The manufacturing method of the tetrazo solution was the same as in Example 1. On the other hand, acetoacetanilide 1 was added to 200 parts of water.
7.0 parts, 0.9 parts of 5-acetoacetylamino-2-hydroxybenzoic acid and 10 parts of caustic soda were added and dissolved. To this solution, 45 parts of 80% acetic acid was added little by little to form a suspension, and the tetrazo solution was added to this suspension in about 20 minutes. During this period, the reaction temperature was kept at about 15 ° C. In the obtained disazo pigment slurry, a solution prepared by dissolving 17.0 parts of acetoacetanilide, 0.9 parts of acetoaceto-4-phenetidide, and 10 parts of caustic soda in 200 parts of water and a tetrazo solution were not simultaneously released during the reaction. It took about 20 minutes to add while adjusting the flow rates of both solutions.
The reaction temperature during this period was also maintained at about 15 ° C. The obtained disazo pigment slurry was treated in the same manner as in Example 1 to obtain a wet cake having a pigment content of 30.0%. The inking method was the same as in Example 1 to obtain the final ink.
【００３１】[0031]
【実施例５】テトラゾ溶液の製造法は実施例１と同様に
行った。一方、水３５０部にアセトアセトアニリド３
４．０部と２−アセトアセチルアミノ安息香酸０．９部
及び苛性ソーダ１９．６部を加えて溶解した。この溶液
に８０％酢酸４５部を少しずつ加えて懸濁液とし、これ
に前記テトラゾ溶液を約３０分要して加えた。この間の
反応温度は約１５℃に保持した。得られたジスアゾ顔料
のスラリーに、水５０部にアセトアセト−２−フェネチ
ジド１．８部及び苛性ソーダ０．４部で溶解した溶液と
テトラゾ溶液を同時に、テトラゾが反応中に遊離しない
ように両溶液の流速を調整しながら約１０分要して加え
た。この間の反応温度も約１５℃に保持した。 得られ
たジスアゾ顔料スラリーは実施例１と同様の操作を行い
顔料分３０．０％のウェットケーキを得た。インキ化の
方法は実施例１と同様に行い最終インキを得た。[Example 5] The tetrazo solution was manufactured in the same manner as in Example 1. Meanwhile, acetoacetanilide 3 was added to 350 parts of water.
4.0 parts, 0.9 parts of 2-acetoacetylaminobenzoic acid and 19.6 parts of caustic soda were added and dissolved. To this solution, 45 parts of 80% acetic acid was added little by little to form a suspension, and the tetrazo solution was added to this suspension in about 30 minutes. During this period, the reaction temperature was kept at about 15 ° C. Into the obtained slurry of disazo pigment, a solution prepared by dissolving 1.8 parts of acetoacet-2-phenetidide and 0.4 part of caustic soda in 50 parts of water and a tetrazo solution at the same time are prepared so that tetrazo is not released during the reaction. It took about 10 minutes to add while adjusting the flow rate. The reaction temperature during this period was also maintained at about 15 ° C. The obtained disazo pigment slurry was treated in the same manner as in Example 1 to obtain a wet cake having a pigment content of 30.0%. The inking method was the same as in Example 1 to obtain the final ink.
【００３２】[0032]
【実施例６】テトラゾ溶液の製造法は実施例１と同様に
行った。一方、水３５０部にアセトアセトアニリド３
３．６部と４−アセトアセチルアミノベンゼンスルホン
酸１．０部及び苛性ソーダ１９．６部を加えて溶解し
た。この溶液に８０％酢酸４５部を少しずつ加えて懸濁
液とし、これに前記テトラゾ溶液を約３０分要して加え
た。この間の反応温度は約１５℃に保持した。得られた
ジスアゾ顔料のスラリーに、水５０部にアセトアセト−
４−プロポキシアニリド１．４部及び苛性ソーダ０．４
部で溶解した溶液とテトラゾ溶液を同時に、テトラゾが
反応中に遊離しないように両溶液の流速を調整しながら
約１０分要して加えた。この間の反応温度も約１５℃に
保持した。 得られたジスアゾ顔料スラリーは実施例１
と同様の操作を行い顔料分３０．０％のウェットケーキ
を得た。インキ化の方法は実施例１と同様に行い最終イ
ンキを得た。Example 6 The method for producing a tetrazo solution was the same as in Example 1. Meanwhile, acetoacetanilide 3 was added to 350 parts of water.
3.6 parts, 4-acetoacetylaminobenzenesulfonic acid 1.0 part and caustic soda 19.6 parts were added and dissolved. To this solution, 45 parts of 80% acetic acid was added little by little to form a suspension, and the tetrazo solution was added to this suspension in about 30 minutes. During this period, the reaction temperature was kept at about 15 ° C. Acetoacetate was added to 50 parts of water in the obtained disazo pigment slurry.
1.4 parts of 4-propoxyanilide and 0.4 of caustic soda
The solution dissolved in 1 part and the tetrazo solution were added simultaneously, taking about 10 minutes while adjusting the flow rate of both solutions so that tetrazo was not released during the reaction. The reaction temperature during this period was also maintained at about 15 ° C. The resulting disazo pigment slurry was prepared as in Example 1.
The same operation as above was performed to obtain a wet cake having a pigment content of 30.0%. The inking method was the same as in Example 1 to obtain the final ink.
【００３３】[0033]
【実施例７】テトラゾ溶液の製造法は実施例１と同様に
行った。一方、水３５０部にアセトアセトアニリド３
４．０部と４−アセトアセチルアミノベンゼンスルホン
酸１．１部及び苛性ソーダ１９．６部を加えて溶解し
た。この溶液に８０％酢酸４５部を少しずつ加えて懸濁
液とし、これに前記テトラゾ溶液を約３０分要して加え
た。この間の反応温度は約１５℃に保持した。得られた
ジスアゾ顔料のスラリーに、水５０部にアセトアセト−
４−ブチキシアニリド１．０部及び苛性ソーダ０．４部
で溶解した溶液とテトラゾ溶液を同時に、テトラゾが反
応中に遊離しないように両溶液の流速を調整しながら約
１０分要して加えた。この間の反応温度も約１５℃に保
持した。 得られたジスアゾ顔料スラリーは実施例１と
同様の操作を行い顔料分３０．０％のウェットケーキを
得た。インキ化の方法は実施例１と同様に行い最終イン
キを得た。Example 7 The method for producing a tetrazo solution was the same as in Example 1. Meanwhile, acetoacetanilide 3 was added to 350 parts of water.
4.0 parts, 1.1 parts of 4-acetoacetylaminobenzenesulfonic acid and 19.6 parts of caustic soda were added and dissolved. To this solution, 45 parts of 80% acetic acid was added little by little to form a suspension, and the tetrazo solution was added to this suspension in about 30 minutes. During this period, the reaction temperature was kept at about 15 ° C. Acetoacetate was added to 50 parts of water in the obtained disazo pigment slurry.
A solution prepared by dissolving 1.0 part of 4-butoxyanilide and 0.4 part of caustic soda and the tetrazo solution were added simultaneously, taking about 10 minutes while adjusting the flow rates of both solutions so that tetrazo was not released during the reaction. The reaction temperature during this period was also maintained at about 15 ° C. The obtained disazo pigment slurry was treated in the same manner as in Example 1 to obtain a wet cake having a pigment content of 30.0%. The inking method was the same as in Example 1 to obtain the final ink.
【００３４】[0034]
【実施例８】テトラゾ溶液の製造法は実施例１と同様に
行った。一方、水３５０部にアセトアセトアニリド３
１．９部と４−アセトアセチルアミノ−２ーメチル安息
香酸２．４部及び苛性ソーダ１９．６部を加えて溶解し
た。この溶液に８０％酢酸４５部を少しずつ加えて懸濁
液とし、これに前記テトラゾ溶液を約３０分要して加え
た。この間の反応温度は約１５℃に保持した。得られた
ジスアゾ顔料のスラリーに、水５０部にアセトアセト−
２−クロロ−４−フェネチジド２．５部及び苛性ソーダ
０．４部で溶解した溶液とテトラゾ溶液を同時に、テト
ラゾが反応中に遊離しないように両溶液の流速を調整し
ながら、約１０分要して加えた。この間の反応温度も約
１５℃に保持した。 得られたジスアゾ顔料スラリーは
実施例１と同様の操作を行い顔料分３０．０％のウェッ
トケーキを得た。インキ化の方法は実施例１と同様に行
い最終インキを得た。Example 8 The manufacturing method of the tetrazo solution was performed in the same manner as in Example 1. Meanwhile, acetoacetanilide 3 was added to 350 parts of water.
1.9 parts, 2.4 parts of 4-acetoacetylamino-2-methylbenzoic acid and 19.6 parts of caustic soda were added and dissolved. To this solution, 45 parts of 80% acetic acid was added little by little to form a suspension, and the tetrazo solution was added to this suspension in about 30 minutes. During this period, the reaction temperature was kept at about 15 ° C. Acetoacetate was added to 50 parts of water in the obtained disazo pigment slurry.
It takes about 10 minutes while simultaneously adjusting the flow rate of the solution in which 2.5 parts of 2-chloro-4-phenetide and 0.4 parts of caustic soda and the tetrazo solution are simultaneously dissolved so that tetrazo is not released during the reaction. Added. The reaction temperature during this period was also maintained at about 15 ° C. The obtained disazo pigment slurry was treated in the same manner as in Example 1 to obtain a wet cake having a pigment content of 30.0%. The inking method was the same as in Example 1 to obtain the final ink.
【００３５】[0035]
【比較例１】テトラゾ溶液の製造法は実施例１と同様に
行った。一方、水４００部にアセトアセトアニリド３
５．４部を苛性ソーダ２０部を加えて溶解した。この溶
液に８０％酢酸４５部を少しずつ加えて懸濁液とし、こ
れに前記テトラゾ溶液を約３０分要して加えた。この間
の反応温度は約１５℃に保持した。 得られたジスアゾ
顔料スラリーは実施例１と同様の操作を行い顔料分３
０．０％のウェットケーキを得た。インキ化の方法は実
施例１と同様に行い最終インキを得た。Comparative Example 1 The manufacturing method of the tetrazo solution was the same as in Example 1. On the other hand, acetoacetanilide 3 in 400 parts of water
20 parts of caustic soda was added to dissolve 5.4 parts. To this solution, 45 parts of 80% acetic acid was added little by little to form a suspension, and the tetrazo solution was added to this suspension in about 30 minutes. During this period, the reaction temperature was kept at about 15 ° C. The obtained disazo pigment slurry was treated in the same manner as in Example 1 to give a pigment content of 3
A wet cake of 0.0% was obtained. The inking method was the same as in Example 1 to obtain the final ink.
【００３６】[0036]
【比較例２】テトラゾ溶液の製造法は実施例１と同様に
行った。一方、水４００部にアセトアセトアニリド３
４．０部と５−アセトアセチルアミノ−２−ヒドロキシ
安息香酸１．８部及び苛性ソーダ２０部を加えて溶解し
た。この溶液に８０％酢酸４５部を少しずつ加えて懸濁
液とし、これに前記テトラゾ溶液を約３０分要して加え
た。この間の反応温度は約１５℃に保持した。 得られ
たジスアゾ顔料スラリーは実施例１と同様の操作を行い
顔料分３０．０％のウェットケーキを得た。インキ化の
方法は実施例１と同様に行い最終インキを得た。Comparative Example 2 The manufacturing method of the tetrazo solution was the same as in Example 1. On the other hand, acetoacetanilide 3 in 400 parts of water
4.0 parts, 1.8 parts of 5-acetoacetylamino-2-hydroxybenzoic acid and 20 parts of caustic soda were added and dissolved. To this solution, 45 parts of 80% acetic acid was added little by little to form a suspension, and the tetrazo solution was added to this suspension in about 30 minutes. During this period, the reaction temperature was kept at about 15 ° C. The obtained disazo pigment slurry was treated in the same manner as in Example 1 to obtain a wet cake having a pigment content of 30.0%. The inking method was the same as in Example 1 to obtain the final ink.
【００３７】以上の結果を表１にまとめた。L* はイン
キの透明性を示しその値が小の方が透明性大、濃度はコ
ーサー値（反射率濃度）で示しその値が大の方が濃度
大、流動性はスプレッドメーター測定器での６０秒値
（ｍｍ）で示しその値が大の方が流動性大である。水切
れ時間はオープンフラッシング工程で水が出てくる時の
時間を示しこの値が小さい方がフラッシング性は良好で
ある。The above results are summarized in Table 1. L * indicates the transparency of the ink. The smaller the value, the greater the transparency, the density is the coercer value (reflectance density), the greater the value, the greater the density, and the fluidity is the spread meter measuring value. It is indicated by a value of 60 seconds (mm), and the larger the value, the larger the fluidity. The drainage time indicates the time when water comes out in the open flushing step, and the smaller this value is, the better the flushing property is.
【００３８】 表１ 透明性 濃度 流動性 水切れ時間 実施例１ L* ＝60.2 １．８０ １９．０ ３分４０秒 実施例２ L* ＝60.3 １．８０ １９．０ ３分４５秒 実施例３ L* ＝58.1 １．８５ １９．５ ２分５０秒 実施例４ L* ＝59.3 １．８２ １８．８ ３分００秒 実施例５ L* ＝59.4 １．７８ １８．９ ３分０５秒 実施例６ L* ＝60.1 １．７９ １９．１ ２分５５秒 実施例７ L* ＝59.9 １．７７ １８．７ ３分１０秒 実施例８ L* ＝60.5 １．７９ １８．９ ３分１５秒 比較例１ L* ＝80.5 １．５０ ２１．０ ３分２０秒 比較例２ L* ＝66.8 １．６５ １７．８ ８分５５秒 Table 1 Transparency Concentration Fluidity Water drainage time Example 1 L * = 60.2 1.80 19.0 3 minutes 40 seconds Example 2 L * = 60.3 1.80 19.0 3 minutes 45 seconds Example 3 L * = 58.1 1.85 19.5 2 minutes 50 seconds Example 4 L * = 59.3 1.82 18.8 3 minutes 00 seconds Example 5 L * = 59.4 1.78 18.9 3 minutes 05 seconds Example 6 L * = 60.1 1.79 19.1 2 minutes 55 seconds Example 7 L * = 59.9 1.77 18.7 3 minutes 10 seconds Example 8 L * = 60.5 1.79 18.9 3 minutes 15 seconds Comparative Example 1 L * = 80.5 1.50 21.0 3 minutes 20 seconds Comparative example 2 L * = 66.8 1.65 17.8 8 minutes 55 seconds
Claims (7)
ゾ化物とアセトアセトアニリド系化合物をカップリング
させてなるジスアゾ顔料において、該アセトアセトアニ
リド系化合物が、アセトアセトアニリド８０〜９９モル
％、下記式（１）で示される極性基含有アセトアセトア
ニリド化合物０．５〜１０モル％および下記式（２）で
示されるアルコキシ基含有アセトアセトアニリド化合物
０．５〜１０モル％からなることを特徴とするジスアゾ
顔料。式（１） ＣＨ3ＣＯＣＨ2ＣＯＮＨ−Ｘ （式中、Ｘはカルボン酸基、スルホン酸基およびこれら
の金属塩からなる群から選ばれる同一又は異なる１〜４
個の置換基を有するフェニル基（該フェニル基は、置換
可能な位置がメチル基、メトキシ基、水酸基または塩素
原子で置換されていてもよい。）を示す。） 式（２） ＣＨ3ＣＯＣＨ2ＣＯＮＨ−Ｙ （式中、Ｙは炭素数２〜４のアルコキシ基を有するフェ
ニル基（該フェニル基は、置換可能な位置がメチル基、
メトキシ基、水酸基または塩素原子で置換されていても
よい。）を示す。）1. A disazo pigment obtained by coupling a tetrazolate of 3,3′-dichlorobenzidine and an acetoacetanilide compound, wherein the acetoacetanilide compound is 80 to 99 mol% of acetoacetanilide, and the following formula (1): A disazo pigment comprising 0.5 to 10 mol% of a polar group-containing acetoacetanilide compound represented by and an alkoxy group-containing acetoacetanilide compound represented by the following formula (2). Equation (1) CH 3 COCH 2 CONH -X ( wherein, X is the same or different 1 to 4 selected from the group consisting of carboxylic acid, sulfonic acid and their metal salts
Shows a phenyl group having 4 substituents (the phenyl group may be substituted at a substitutable position with a methyl group, a methoxy group, a hydroxyl group or a chlorine atom). ) Formula (2) CH 3 in COCH 2 CONH-Y (wherein, Y represents a phenyl group (the phenyl group, substitutable position is a methyl group having an alkoxy group having 2 to 4 carbon atoms,
It may be substituted with a methoxy group, a hydroxyl group or a chlorine atom. ) Is shown. )
トアセトアニリド化合物およびアルコキシ基含有アセト
アセトアニリド化合物の混合物と３，３’−ジクロロベ
ンジジンのテトラゾ液とを反応させることを特徴とする
請求項１記載のジスアゾ顔料の製造方法。2. The disazo pigment according to claim 1, wherein a mixture of acetoacetanilide, a polar group-containing acetoacetanilide compound and an alkoxy group-containing acetoacetanilide compound is reacted with a tetrazo solution of 3,3′-dichlorobenzidine. Manufacturing method.
よび極性基含有アセトアセトアニリド化合物の混合物と
３，３’−ジクロロベンジジンのテトラゾ液とを予め反
応させた後、アルコキシ基含有アセトアセトアニリド化
合物と３，３’−ジクロロベンジジンのテトラゾ液とを
反応させることを特徴とする請求項１記載のジスアゾ顔
料の製造方法。3. A mixture of acetoacetanilide and a polar group-containing acetoacetanilide compound and a tetrazo solution of 3,3′-dichlorobenzidine are preliminarily reacted in the same container, and then an alkoxy group-containing acetoacetanilide compound and 3,3 ′ are reacted. 2. The method for producing a disazo pigment according to claim 1, which comprises reacting a tetrazo solution of'-dichlorobenzidine.
よび極性基含有アセトアセトアニリド化合物の混合物と
３，３’−ジクロロベンジジンのテトラゾ液とを予め反
応させた後、アセトアセトアニリドおよびアルコキシ基
含有アセトアセトアニリド化合物の混合物と３，３’−
ジクロロベンジジンのテトラゾ液とを反応させることを
特徴とする請求項１記載のジスアゾ顔料の製造方法。4. A mixture of acetoacetanilide and a polar group-containing acetoacetanilide compound is preliminarily reacted with a tetrazo solution of 3,3′-dichlorobenzidine in the same container, and then the acetoacetanilide and the alkoxy group-containing acetoacetanilide compound are reacted. Mixture and 3,3'-
The method for producing a disazo pigment according to claim 1, which comprises reacting dichlorobenzidine with a tetrazo solution.
−ジクロロベンジジンのテトラゾ溶液とアセトアセトア
ニリド系化合物のアルカリ性溶液とを連続的に添加する
方法で行われる請求項２ないし４いずれか記載のジスア
ゾ顔料の製造方法。5. The reaction is 3,3 ′ in a weakly acidic buffer solution.
The method for producing a disazo pigment according to any one of claims 2 to 4, which is carried out by a method of continuously adding a tetrazo solution of dichlorobenzidine and an alkaline solution of an acetoacetanilide compound.
ケーキ状態で印刷インキビヒクルによりフラッシングさ
れることを特徴とする印刷インキの製造方法。6. A method for producing a printing ink, wherein the disazo pigment according to claim 1 is flushed with a printing ink vehicle in a wet cake state.
キビヒクルとからなることを特徴とする印刷インキ。7. A printing ink comprising the disazo pigment according to claim 1 and a printing ink vehicle.
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|---|---|---|---|
| JP2001280885A JP4016624B2 (en) | 2001-09-17 | 2001-09-17 | Disazo pigment, process for producing the same and printing ink composition |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001280885A JP4016624B2 (en) | 2001-09-17 | 2001-09-17 | Disazo pigment, process for producing the same and printing ink composition |
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| Publication Number | Publication Date |
|---|---|
| JP2003082253A true JP2003082253A (en) | 2003-03-19 |
| JP4016624B2 JP4016624B2 (en) | 2007-12-05 |
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|---|---|---|---|
| JP2001280885A Expired - Lifetime JP4016624B2 (en) | 2001-09-17 | 2001-09-17 | Disazo pigment, process for producing the same and printing ink composition |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007284641A (en) * | 2006-04-20 | 2007-11-01 | Dainippon Ink & Chem Inc | Disazo pigment composition, method for producing the same, and printing ink |
| JP2018123321A (en) * | 2017-02-01 | 2018-08-09 | 東洋インキＳｃホールディングス株式会社 | Active energy ray-curable ink composition, method for producing the same and coating film prepared using ink composition |
-
2001
- 2001-09-17 JP JP2001280885A patent/JP4016624B2/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007284641A (en) * | 2006-04-20 | 2007-11-01 | Dainippon Ink & Chem Inc | Disazo pigment composition, method for producing the same, and printing ink |
| JP2018123321A (en) * | 2017-02-01 | 2018-08-09 | 東洋インキＳｃホールディングス株式会社 | Active energy ray-curable ink composition, method for producing the same and coating film prepared using ink composition |
| JP7030268B2 (en) | 2017-02-01 | 2022-03-07 | 東洋インキＳｃホールディングス株式会社 | Active energy ray-curable ink composition, its manufacturing method, and a coating film produced using the ink composition. |
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| Publication number | Publication date |
|---|---|
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