JPH0157147B2 - - Google Patents
Info
- Publication number
- JPH0157147B2 JPH0157147B2 JP58037272A JP3727283A JPH0157147B2 JP H0157147 B2 JPH0157147 B2 JP H0157147B2 JP 58037272 A JP58037272 A JP 58037272A JP 3727283 A JP3727283 A JP 3727283A JP H0157147 B2 JPH0157147 B2 JP H0157147B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- pigment
- fluidity
- carboxyphenylacetoacetate
- acetoaceto
- 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 9
- 239000001052 yellow pigment Substances 0.000 claims description 9
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 claims description 5
- PFENPVAFZTUOOM-UHFFFAOYSA-N phenyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC1=CC=CC=C1 PFENPVAFZTUOOM-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000007598 dipping method Methods 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000976 ink Substances 0.000 description 17
- 239000000049 pigment Substances 0.000 description 14
- -1 3-carboxyphenylacetoacetate Chemical compound 0.000 description 10
- 238000007796 conventional method Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 239000002966 varnish Substances 0.000 description 5
- 239000012530 fluid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 3
- HGVIAKXYAZRSEG-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1C HGVIAKXYAZRSEG-UHFFFAOYSA-N 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- MTCCIVNAHOYAAA-UHFFFAOYSA-N C(=O)(O)C1=C(C=CC=C1)CC(CC(=O)O)=O Chemical compound C(=O)(O)C1=C(C=CC=C1)CC(CC(=O)O)=O MTCCIVNAHOYAAA-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 235000010187 litholrubine BK Nutrition 0.000 description 1
- BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 1
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 1
- JMRJWEJJUKUBEA-UHFFFAOYSA-N p-Chloroacetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1 JMRJWEJJUKUBEA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002994 raw material Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Description
【発明の詳細な説明】
本発明は各種の用途、例えば印刷インキとして
使用した場合、極めて優れた流動性を有するジス
アゾ黄色顔料の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a process for producing disazo yellow pigments which have excellent fluidity when used in various applications, for example as printing inks.
顔料を印刷インキとして使用する場合、印刷速
度の高速化や紙質の低下に対応するため、流動性
の優れたものが望まれている。カーミン6Bやフ
タロシアニン顔料に比べて、従来のジスアゾ黄色
顔料では「ツボ上り」と称し、インキの流動性が
時間と共に低下し、遂には流れなくなる現象が起
り、作業上著しい困難をきたしていた。このよう
な欠点を改良する方法として、アミン処理による
方法や界面活性剤処理をする方法が知られている
が、いずれも満足のいくものを得ることはできな
かつた。 When pigments are used as printing inks, they are desired to have excellent fluidity in order to cope with increased printing speeds and deterioration of paper quality. Compared to carmine 6B and phthalocyanine pigments, conventional disazo yellow pigments suffer from a phenomenon known as ``point-up'', where the fluidity of the ink decreases over time and eventually stops flowing, causing considerable difficulties in working. As methods for improving these defects, methods using amine treatment and methods using surfactant treatment are known, but neither method has been able to provide a satisfactory result.
本発明者等は鋭意研究の結果、カツプラー成分
として特定の化合物を使用することにより極めて
優れた流動性を有するジスアゾ黄色顔料が得られ
ることを見出し、本発明を完成させるに至つた。 As a result of intensive research, the present inventors have discovered that a disazo yellow pigment having extremely excellent fluidity can be obtained by using a specific compound as a coupler component, and have completed the present invention.
即ち、本発明は、
３，3′−ジクロルベンジジンのテトラゾ化物
と、アセトアセトアニリド類80〜99モル％および
下記一般式()で示されるフエニルアセトアセテ
ート20〜１モル％を混合してなる下漬液とをカツ
プリングさせることを特徴とするジスアゾ黄色顔
料の製造法。 That is, the present invention comprises a mixture of a tetrazotized product of 3,3'-dichlorobenzidine, 80 to 99 mol% of acetoacetanilides, and 20 to 1 mol% of phenylacetoacetate represented by the following general formula (). A method for producing a disazo yellow pigment, which comprises coupling a disazo yellow pigment with a subsoaking liquid.
（式中、Ｒは水素原子、低級アルキル基又は低級
アルコキシ基を表わす。）
を提供するものである。 (In the formula, R represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group.)
本発明において使用するアセトアセトアニリド
類としては、例えばアセトアセトアニリド、ｏ−
クロルアセトアセトアニリド、ｎ−クロルアセト
アセトアニリド、ｐ−クロルアセトアセトアニリ
ド、アセトアセト−ｏ−トルイジド、アセトアセ
ト−ｏ−アニシジド、アセトアセト−ｍ−キシリ
ジド、アセトアセト−２，５−ジメトキシアニリ
ド、アセトアセト−２，５−ジメトキシ−４−ク
ロルアニリド、アセトアセト−ｐ−アニシジド、
アセトアセト−５−クロル−２−トルイジド、ア
セトアセト−ｐ−トルイシド、アセトアセト−ｐ
−エトキシアニリド、アセトアセト−２−メチル
−４−ニトロアニリド等があげられる。 Examples of the acetoacetanilide used in the present invention include acetoacetanilide, o-
Chloracetoacetanilide, n-chloroacetoacetanilide, p-chloroacetoacetanilide, acetoaceto-o-toluidide, acetoaceto-o-anisidide, acetoaceto-m-xylidide, acetoaceto-2,5-dimethoxyanilide, acetoaceto-2,5-dimethoxy -4-chloranilide, acetoaceto-p-anisidide,
Acetoaceto-5-chloro-2-toluidide, Acetoaceto-p-toluide, Acetoaceto-p
-ethoxyanilide, acetoaceto-2-methyl-4-nitroanilide, and the like.
一方、一般式()で示されるフエニルアセトア
セテートとしては、例えば２−カルボキシフエニ
ルアセトアセテート、３−カルボキシフエニルア
セトアセテート、４−カルボキシフエニルアセト
アセテート、２−メチル−４−カルボキシフエニ
ルアセトアセテート、２−メトキシ−４−カルボ
キシフエニルアセトアセテート等があげられる。 On the other hand, examples of the phenylacetoacetate represented by the general formula () include 2-carboxyphenylacetoacetate, 3-carboxyphenylacetoacetate, 4-carboxyphenylacetoacetate, 2-methyl-4-carboxyphenyl Examples include acetoacetate, 2-methoxy-4-carboxyphenylacetoacetate, and the like.
一般式()で示されるフエニルアセトアセテー
トの使用割合は、流動性と共に十分な着色力を得
るため、通常カツプリング成分の１〜20モル％で
ある。 The proportion of phenylacetoacetate represented by the general formula () is usually 1 to 20 mol % of the coupling component in order to obtain fluidity and sufficient coloring power.
上記の如き原料を用いるジスアゾ黄色顔料の製
造は、従来より公知のジスアゾ黄色顔料の製造方
法に準じて行うことができる。即ち、３，3′−ジ
クロルベンジジンを常法に従つてテトラゾ化し、
一方上述のアセトアセトアニリド類と一般式()
で示されるフエニルアセトアセテートとの混合物
より常法に従つて下漬液を調製し、両者を常法に
従つて混合してカツプリングさせることにより本
発明方法による流動性の優れたジスアゾ黄色顔料
が得られる。もちろん、カツプリング前又はカツ
プリング後に各種の水溶性樹脂、界面活性剤、そ
の他の添加剤を加えて顔料処理を行うこともでき
る。生成した顔料の使用法としては、含水顔料プ
レスケーキとワニス又は樹脂等とを直接混練して
も、また顔料を乾燥した後ワニス又は樹脂等と混
合しても良い。 The production of a disazo yellow pigment using the above raw materials can be carried out according to a conventionally known method for producing a disazo yellow pigment. That is, 3,3'-dichlorobenzidine is tetrazotized according to a conventional method,
On the other hand, the above-mentioned acetoacetanilides and the general formula ()
A disazo yellow pigment with excellent fluidity can be obtained by the method of the present invention by preparing a base solution from the mixture with phenylacetoacetate according to the conventional method, and mixing and coupling the two according to the conventional method. It will be done. Of course, pigment treatment can be carried out by adding various water-soluble resins, surfactants, and other additives before or after coupling. The produced pigment may be used by directly kneading the water-containing pigment press cake with varnish or resin, or by drying the pigment and then mixing it with varnish or resin.
以下、実施例によつて本発明を説明するが、本
発明は実施例のみに限定されるものではない。な
お、例中、「部」とあるのは「重量部」を示す。 EXAMPLES The present invention will be described below with reference to Examples, but the present invention is not limited to the Examples. In addition, in the examples, "parts" indicate "parts by weight."
実施例 １
３，3′−ジクロルベンジジン38.2部を常法に従
つてテトラゾ化してテトラゾ溶液を得た。一方、
アセトアセトアニリド48.1部と３−カルボキシフ
エニルアセトアセテート6.7部とから常法に従つ
て下漬液を調製した。両者を混合してカツプリン
グさせ、得られた顔料を濾過、水洗し、固形分96
部の含水プレスケーキを得た。次いで、オフセツ
トインキワニス500部に上記のプレスケーキを加
え、フラツシヤー中で混練してフラツシングを行
い、脱水後、３本ロールでオフセツトインキを作
成した。平行板粘度計でこのインキの流動性を測
定したところ、30分後も流動性を保持していた。Example 1 38.2 parts of 3,3'-dichlorobenzidine was tetrazotized according to a conventional method to obtain a tetrazo solution. on the other hand,
A dipping solution was prepared from 48.1 parts of acetoacetanilide and 6.7 parts of 3-carboxyphenylacetoacetate according to a conventional method. The two are mixed and combined, and the resulting pigment is filtered and washed with water to reduce the solid content to 96.
A portion of a water-containing press cake was obtained. Next, the above press cake was added to 500 parts of offset ink varnish, kneaded in a flasher for flashing, and after dehydration, an offset ink was prepared using three rolls. When the fluidity of this ink was measured using a parallel plate viscometer, it remained fluid even after 30 minutes.
比較例 １
アセトアセトアニリド53.5部より下漬液を調製
した以外は実施例１と同様にして、顔料の合成及
びオフセツトインキの作成を行つた。このインキ
の流動性を測定したところ、10分後には流動性を
停止した。Comparative Example 1 A pigment was synthesized and an offset ink was prepared in the same manner as in Example 1, except that a base dipping solution was prepared from 53.5 parts of acetoacetanilide. When the fluidity of this ink was measured, the fluidity stopped after 10 minutes.
実施例 ２
３，3′−ジクロルベンジジン38.2部を常法に従
つてテトラゾ化してテトラゾ溶液を得た。一方、
アセトアセト−ｍ−キシリジド55.7部と４−カル
ボキシフエニルアセトアセテート6.7部とから常
法に従つて下漬液を調製した。両者を混合しカツ
プリングさせた後、ロジン溶液（ロジン分として
2.9部）を加え、さらに塩化カルシウム溶液（塩
化カルシウムとして0.7部）を加えて顔料を合成
した。得られた顔料を濾過、水洗し、90℃で乾燥
した。オフセツトインキワニス90部と上記顔料10
部をフーバーマーラー上で混練し、オフセツトイ
ンキワニスを得た。このインキの流動性を測定し
たところ、30分後も流動性を保持していた。Example 2 38.2 parts of 3,3'-dichlorobenzidine was tetrazotized according to a conventional method to obtain a tetrazo solution. on the other hand,
A submerging solution was prepared from 55.7 parts of acetoaceto-m-xylidide and 6.7 parts of 4-carboxyphenylacetoacetate according to a conventional method. After mixing the two and coupling, add the rosin solution (as the rosin part)
2.9 parts) and further added a calcium chloride solution (0.7 parts as calcium chloride) to synthesize a pigment. The obtained pigment was filtered, washed with water, and dried at 90°C. 90 parts of offset ink varnish and 10 parts of the above pigments
The mixture was kneaded on a Huber muller to obtain an offset ink varnish. When the fluidity of this ink was measured, it remained fluid even after 30 minutes.
比較例 ２
アセトアセト−ｍ−キシリジド61.9部より下漬
液を調製した以外は実施例２と同様にして、顔料
の合成及びオフセツトインキの作成を行つた。こ
のインキの流動性を測定したところ、10分後には
流動性を停止した。Comparative Example 2 A pigment was synthesized and an offset ink was prepared in the same manner as in Example 2, except that a subsoak solution was prepared from 61.9 parts of acetoaceto-m-xylidide. When the fluidity of this ink was measured, the fluidity stopped after 10 minutes.
実施例 ３
３，−カルボキシフエニルアセトアセテート6.7
部の代りに２−メチル−４−カルボキシフエニル
アセトアセテート7.1部を用いて下漬液を調製し
た以外は実施例１と同様にして、顔料の合成及び
オフセツトインキの作成を行つた。このインキの
流動性を測定したところ、30分後も流動性を保持
していた。Example 3 3,-Carboxyphenylacetoacetate 6.7
A pigment was synthesized and an offset ink was prepared in the same manner as in Example 1, except that 7.1 parts of 2-methyl-4-carboxyphenylacetoacetate was used instead of 7.1 parts of 2-methyl-4-carboxyphenylacetoacetate to prepare the base solution. When the fluidity of this ink was measured, it remained fluid even after 30 minutes.
実施例 ４
３，−カルボキシフエニルアセトアセテート6.7
部の代りに２−メトキシ−４−カルボキシフエニ
ルアセトアセテート7.6部を用いて下漬液を調製
した以外は実施例１と同様にして、顔料の合成及
びオフセツトインキの作成を行つた。このインキ
の流動性を測定したところ、30分後も流動性を保
持していた。Example 4 3,-Carboxyphenylacetoacetate 6.7
A pigment was synthesized and an offset ink was prepared in the same manner as in Example 1, except that 7.6 parts of 2-methoxy-4-carboxyphenylacetoacetate was used instead of 7.6 parts of 2-methoxy-4-carboxyphenylacetoacetate to prepare a base soaking solution. When the fluidity of this ink was measured, it remained fluid even after 30 minutes.
Claims (1)
と、アセトアセトアニリド類80〜99モル％および
下記一般式()で示されるフエニルアセトアセテ
ート20〜１モル％を混合してなる下漬液とをカツ
プリングさせることを特徴とするジスアゾ黄色顔
料の製造法。 （式中、Ｒは水素原子、低級アルキル基又は低級
アルコキシ基を表わす。）[Scope of Claims] 1 A mixture of a tetrazotized product of 3,3'-dichlorobenzidine, 80 to 99 mol% of acetoacetanilides, and 20 to 1 mol% of phenylacetoacetate represented by the following general formula (). 1. A method for producing a disazo yellow pigment, characterized by coupling a base dipping liquid with (In the formula, R represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3727283A JPS59172551A (en) | 1983-03-09 | 1983-03-09 | Production of yellow dis-azo pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3727283A JPS59172551A (en) | 1983-03-09 | 1983-03-09 | Production of yellow dis-azo pigment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59172551A JPS59172551A (en) | 1984-09-29 |
| JPH0157147B2 true JPH0157147B2 (en) | 1989-12-04 |
Family
ID=12493037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3727283A Granted JPS59172551A (en) | 1983-03-09 | 1983-03-09 | Production of yellow dis-azo pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59172551A (en) |
-
1983
- 1983-03-09 JP JP3727283A patent/JPS59172551A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59172551A (en) | 1984-09-29 |
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