JPS6129971B2 - - Google Patents
Info
- Publication number
- JPS6129971B2 JPS6129971B2 JP10591783A JP10591783A JPS6129971B2 JP S6129971 B2 JPS6129971 B2 JP S6129971B2 JP 10591783 A JP10591783 A JP 10591783A JP 10591783 A JP10591783 A JP 10591783A JP S6129971 B2 JPS6129971 B2 JP S6129971B2
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- disazo
- compound
- acetoacetanilide
- parts
- 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 claims description 65
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 22
- -1 acetoacetanilide compound Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 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 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000976 ink Substances 0.000 description 32
- 238000000034 method Methods 0.000 description 11
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- 238000007639 printing Methods 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- 238000011010 flushing procedure Methods 0.000 description 5
- 238000004040 coloring Methods 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003760 tallow Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- QMBANXLJKPZBTA-UHFFFAOYSA-N 2,4-dimethoxy-3-oxo-n-phenylbutanamide Chemical compound COCC(=O)C(OC)C(=O)NC1=CC=CC=C1 QMBANXLJKPZBTA-UHFFFAOYSA-N 0.000 description 1
- AWLGDBBYLLAWAW-UHFFFAOYSA-N 2-methyl-4-nitro-3-oxo-n-phenylbutanamide Chemical compound [O-][N+](=O)CC(=O)C(C)C(=O)NC1=CC=CC=C1 AWLGDBBYLLAWAW-UHFFFAOYSA-N 0.000 description 1
- KQNZKBRSEJLVEO-UHFFFAOYSA-N 3-oxo-n-(2-oxobenzimidazol-5-yl)butanamide Chemical compound C1=C(NC(=O)CC(=O)C)C=CC2=NC(=O)N=C21 KQNZKBRSEJLVEO-UHFFFAOYSA-N 0.000 description 1
- LPDSNGAFAJYVKH-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3-dichloroaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C(Cl)=C1Cl LPDSNGAFAJYVKH-UHFFFAOYSA-N 0.000 description 1
- LHECBTWFKAHFAS-UHFFFAOYSA-N 4-(4-aminophenyl)-6,6-dichlorocyclohexa-1,3-dien-1-amine Chemical compound C1C(Cl)(Cl)C(N)=CC=C1C1=CC=C(N)C=C1 LHECBTWFKAHFAS-UHFFFAOYSA-N 0.000 description 1
- UISOMGWVFAGXKI-UHFFFAOYSA-N 4-acetamido-3-oxo-n-phenylbutanamide Chemical compound CC(=O)NCC(=O)CC(=O)NC1=CC=CC=C1 UISOMGWVFAGXKI-UHFFFAOYSA-N 0.000 description 1
- WVIQQZZIPALOSD-UHFFFAOYSA-N 4-chloro-2-methyl-3-oxo-n-phenylbutanamide Chemical compound ClCC(=O)C(C)C(=O)NC1=CC=CC=C1 WVIQQZZIPALOSD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 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 1
- MOUVJGIRLPZEES-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(NC(=O)CC(C)=O)=C(OC)C=C1Cl MOUVJGIRLPZEES-UHFFFAOYSA-N 0.000 description 1
- MJGLMEMIYDUEHA-UHFFFAOYSA-N n-(4-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1 MJGLMEMIYDUEHA-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 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 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
本発明は、ジスアゾ顔料組成物に関し、各種の
用途、例えば、印刷インキ、塗料等、特に紙用グ
ラビアインキ用顔料として有用な新規なジスアゾ
顔料組成物の提供を目的とする。
従来、グラビアインキ用顔料として、ジクロロ
ベンジジンとアセトアセトアニライド類から得ら
れるジスアゾ顔料が広く使用されているが、これ
らの顔料を使用したグラビアインキを用いて紙面
を印刷すると、インキの紙へのしみ込みが激しく
印刷面の光沢や着色力が劣るという欠点があり、
この欠点は使用する紙が低級品になる程顕著であ
る。また、上記ジスアゾ顔料は、塗料、他の印刷
インキ等に広く使用されているが、例えば、オフ
セツトインキ等の印刷インキに使用する際、その
フラツシング時の加熱により着色力を失うという
欠点がある。
このような欠点を改善するために、特公昭45−
11026号、同47−50767号、同53−35090号、同55
−10630号、同55−49087号、特開昭53−41322号
公報等に記載の方法が提案されているが、これら
の方法では、グラビアインキ用顔料としては何ら
改善されず、またフラツシング時の耐熱性の改良
も満足できるものではない。
本発明者は上記の如き従来技術の欠点を解決す
べく鋭意研究の結果、ジスアゾ顔料の構成成分で
あるアセトアセトアニライド系化合物の１部を他
の特定の化合物で置換したジスアゾ顔料組成物
が、グラビアインキ用顔料としてのみならず、塗
料、他の印刷インキ用として非常に改良された顔
料であることを知見して本発明は完成した。
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をアセトアセトアニライド系
化合物にカツプリングさせてなるジスアゾ顔料に
おいて、上記アセトアセトアニライド系化合物の
約0.5〜20モル％が下記の一般式（）で表わさ
れる化合物で置換されていることを特徴とするジ
スアゾ顔料組成物である。
（但し、式中のR1は、１個または複数の水素原
子、メチル基、エチル基、メトキシ基、ニトロ基
ハロゲン原子またはエトキシ基であり、R2およ
びR3は水素原子、メチル基またはエチル基であ
り、ｎは１または２である。）
本発明を詳細に説明すると、本発明において使
用する３・3′−ジクロロベンジジンおよび一般式
（）の化合物以外のアセトアセトアニライド系
化合物は公知であり、例えば、アセトアセトアニ
ライド、０−クロルアセトアセトアニライド、Ｐ
−クロルアセトアセトアニライド、４−クロル−
２・５−ジメトキシアセトアセトアニライド、
２・４−ジメトキシアセトアセトアニライド、０
−アセトアセトアニシダイド、０−アセトアセト
トルイダイド、２・４−アセトアセトキシリダイ
ド、Ｐ−アセトアセトアニシダイド、Ｐ−アセト
アセトトルイダイド、４−クロル−２−メチル−
アセトアセトアニライド、Ｐ−エトキシアセトア
セトアニライド、４−ニトロ−２−メチルアセト
アセトアニライド、４−アセトアセトアミノフタ
ルイミド、５−アセトアセトアミノベンツイミダ
ゾロン、４−ベンゾイルアミノ−２・５−ジエト
キシアセトアセトアニライド、４−アセチルアミ
ノ−アセトアセトアニライド等があげられる。
上記の公知のアセトアセトアニライド系化合物
の１部を置換するための前記一般式（）で表わ
される化合物としては、例えば２−、３−または
４−アセトアセトアミノフエニル尿素、２−、３
−または４−アセトアセトアミノ−Ｐ−、ｍ−、
または０−フエニレンジ尿素およびそれらのメチ
ル、エチル、メトキシ、ニトロ、ハロゲン、エト
キシ置換体等があり、特に好ましいのは４−アセ
トアセトアミノフエニル尿素である。このような
化合物は、前述のアセトアセトアニライド系化合
物の約0.5モル〜約20モル％、好ましくは約1.0モ
ル〜約10モル％の割合を置換する。
上記の如き原料を用いる本発明のジスアゾ顔料
組成物の製造方法は、従来公知のジスアゾ顔料の
製造方法に準じて行うことができる。すなわち、
３・3′−ジクロロベンジジンを常法に従つてテト
ラゾ化し、一方、上述の一般式（）の化合物と
アセトアセトアニライド系化合物とからなる混合
物を用いて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耐熱性の改善されたジスア
ゾ顔料組成物が得られる。また、上記方法におい
て一般式（）の化合物によりアセトアセトアニ
ライド系化合物の20モル％以上を置換して同様に
カツプリング反応を行つた後、これに一般式
（）の化合物を置換しないで得たジスアゾ顔料
を混合して、一般式（）の化合物の使用比率を
アセトアセトアニライド系化合物の0.5〜20モル
％に調整しても同効であり、更に一般式（）の
化合物のみを使用したジスアゾ顔料を予め製造し
ておき、これを所定の比率で一般のジスアゾ顔料
に混合して本発明のジスアゾ顔料を製造してもよ
い。このような後混合の方法を使用する場合は、
混合される顔料が乾燥される前の状態であるのが
好ましい。
以上の如き本発明の顔料組成物は、カツプリン
グ中あるいはカツプリング後に公知の方法に準じ
て、各種の脂肪族アミン、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。特にカツプリング中あるいはカツ
プリング後に、顔料100重量部あたり約１〜25重
量部の長鎖脂肪族アミン、例えば、獣脂アルキル
アミン、獣脂アルキルプロピレンジアミン、アル
キルヒドロキシプロピレンジアミン、ジアルキル
ジエチレントリアミン等を添加して顔料処理を行
うことによつて、本発明で得られる顔料組成物の
インキや塗料その他の媒体中における各種性能が
向上する。
以上の如き本発明方法により得られるジスアゾ
顔料組成物は、従来のジスアゾ顔料に比較して同
等の鮮明性等を有し、且つ従来のジスアゾ顔料お
よび前記引用公報記載の方法によるジスアゾ顔料
が、グラビアインキ用としては前述の如き欠点を
有するに対し、本発明によるジスアゾ顔料組成物
はこのような欠点が克服されている。また、本発
明によるジスアゾ顔料は塗料やオフセツトインキ
等の印刷インキ用としても非常に改良されてい
る。すなわち、ジスアゾ顔料を塗料や印刷インキ
に使用する場合、顔料を顔料の水性ペーストから
フラツシング法により有機相移行させているが、
従来のジスアゾ顔料はこのフラツシング操作中に
顔料の粒子成長が起こり、着色力の著しい低下が
生じたが、本発明によるジスアゾ顔料組成物はこ
のフラツシング時に操作温度が上昇してもこのよ
うな欠点は全く生じることがなく、前記引用公報
記載の方法によるジスアゾ顔料以上にすぐれた印
刷インキや塗料を与えるものである。
次に実施例をあげて本発明を具体的に説明す
る。なお、文中部または％とあるのは特に断りの
ない限り重量基準である。
実施例 １
３・3′−ジクロロベンジジン30部を常法に従つ
てテトラゾ化してテトラゾニウム塩溶液を得る。
一方、アセトアセトアニライド42.2部と、４−ア
セトアセトアミノフエニル尿素3.0部とから常法
に従つて下漬液を調節する。両液を混合しカツプ
リングさせ、得られた顔料を過、水洗、乾燥、
粉砕し、75.3部の本発明のジスアゾ顔料組成物を
得た。該顔料14部をライムロジンワニス86部（固
形分40％）中に加えてペイントコンデイシヨナー
を用いて分散させ、100部のグラビアインキを得
た。該インキを用いて紙にグラビア印刷を行つた
ところ、従来のジスアゾ顔料を使用した場合に比
して色相鮮明であり、著しく改善された光沢およ
び着色力を有する印刷物が得られた。
実施例 ２
実施例１におけるカツプリング混合物に市販の
獣脂アルキルプロピレンジアミン5.3部を混合
し、以下同様にして本発明の顔料組成物を得た。
該顔料組成物は実施例１で得られた本発明の顔料
組成物よりも更に各種の性能が改善されていた。
実施例 ３
実施例１におけるアセトアセトアニライドに代
えて、アセトアセト−Ｐ−トルイダイド46.7部お
よびＰ−アセトアセトアミノフエニル尿素1.8部
を使用し、他は実施例１と同様にして本発明のジ
スアゾ顔料組成物を得た。該顔料組成物は実施例
１のものと同様に各種の性能においてすぐれてい
た。
実施例 ４
実施例１におけるアセトアセトアニライドに代
えて、等モル量のアセトアセト−Ｏ−トルイダイ
ドを用い、他は実施例１と同様にして、実施例１
におけると同様なジスアゾ顔料組成物が得られ
た。
実施例 ５
実施例１の本発明の顔料を用いてオフセツトイ
ンキを調製し、従来公知の同種顔料を使用したオ
フセツトインキと比較したところ下記第１表の結
果を得た。
The present invention relates to a disazo pigment composition, and an object of the present invention is to provide a novel disazo pigment composition useful for various uses, such as printing inks, paints, etc., particularly as a pigment for paper gravure inks. Conventionally, disazo pigments obtained from dichlorobenzidine and acetoacetanilides have been widely used as pigments for gravure inks, but when printing on paper with gravure inks containing these pigments, the ink's impact on the paper The drawback is that it soaks in heavily and the gloss and coloring power of the printed surface is inferior.
This drawback becomes more pronounced as the paper used becomes lower grade. In addition, the above-mentioned disazo pigments are widely used in paints and other printing inks, but when used in printing inks such as offset inks, they have the disadvantage that they lose their coloring power due to heating during flushing. . In order to improve these shortcomings, the special public
No. 11026, No. 47-50767, No. 53-35090, No. 55
-10630, No. 55-49087, Japanese Patent Application Laid-open No. 53-41322, etc., but these methods do not provide any improvement as a pigment for gravure ink, and they do not improve the pigment during flushing. The improvement in heat resistance is also not satisfactory. As a result of intensive research to solve the above-mentioned drawbacks of the prior art, the present inventors have developed a disazo pigment composition in which a part of the acetoacetanilide compound, which is a component of the disazo pigment, is replaced with another specific compound. The present invention was completed based on the finding that the pigment is a highly improved pigment not only for gravure ink, but also for paints and other printing inks. That is, the present invention provides a disazo pigment in which a tetrazotized product of 3,3-dichlorobenzidine is coupled to an acetoacetanilide compound, in which about 0.5 to 20 mol% of the acetoacetanilide compound has the following general formula: This is a disazo pigment composition characterized in that it is substituted with a compound represented by (). (However, R 1 in the formula is one or more hydrogen atoms, a methyl group, an ethyl group, a methoxy group, a nitro group, a halogen atom, or an ethoxy group, and R 2 and R 3 are a hydrogen atom, a methyl group, or an ethyl group. (n is 1 or 2.) To explain the present invention in detail, the acetoacetanilide compounds other than 3,3'-dichlorobenzidine and the compound of general formula () used in the present invention are known For example, acetoacetanilide, 0-chloroacetoacetanilide, P
-Chloracetoacetanilide, 4-chloro-
2,5-dimethoxyacetoacetanilide,
2,4-dimethoxyacetoacetanilide, 0
-Acetoacetoanisidide, 0-acetoacetotoluidide, 2,4-acetoacetoxylidide, P-acetoacetoanisidide, P-acetoacetotoluidide, 4-chloro-2-methyl-
Acetoacetanilide, P-ethoxyacetoacetanilide, 4-nitro-2-methylacetoacetanilide, 4-acetoacetaminophthalimide, 5-acetoacetaminobenzimidazolone, 4-benzoylamino-2.5- Examples include diethoxyacetoacetanilide and 4-acetylaminoacetoacetanilide. Examples of the compound represented by the general formula () for substituting a part of the above-mentioned known acetoacetanilide compounds include 2-, 3- or 4-acetoacetaminophenyl urea, 2-, 3-acetoacetaminophenyl urea,
- or 4-acetoacetamino-P-, m-,
and 0-phenylene diurea and methyl, ethyl, methoxy, nitro, halogen, and ethoxy substituted products thereof, and particularly preferred is 4-acetoacetaminophenyl urea. Such compounds replace about 0.5 mol to about 20 mol %, preferably about 1.0 mol to about 10 mol % of the aforementioned acetoacetanilide compounds. The method for producing the disazo pigment composition of the present invention using the above raw materials can be carried out in accordance with conventionally known methods for producing disazo pigments. That is,
3,3'-Dichlorobenzidine was tetrazotized according to a conventional method, and a submerging solution was prepared according to a conventional method using a mixture consisting of the compound of the above-mentioned general formula () and an acetoacetanilide compound. A disazo pigment composition with improved heat resistance can be obtained by the method of the present invention by mixing and coupling the two in a conventional manner. In addition, in the above method, after replacing 20 mol% or more of the acetoacetanilide compound with the compound of general formula () and performing a coupling reaction in the same manner, a compound of general formula () was obtained without substituting it with the compound of general formula (). The same effect was obtained even if a disazo pigment was mixed and the ratio of the compound of general formula () used was adjusted to 0.5 to 20 mol% of the acetoacetanilide compound, and furthermore, only the compound of general formula () was used. The disazo pigment of the present invention may be produced by preparing a disazo pigment in advance and mixing it with a general disazo pigment at a predetermined ratio. When using this post-mixing method,
Preferably, the pigments to be mixed are in a state before being dried. The pigment composition of the present invention as described above may be subjected to pigment treatment by adding various aliphatic amines, various water-soluble resins, surfactants, and other additives according to known methods during or after coupling. You can also do it. In particular, during or after coupling, pigments are treated by adding about 1 to 25 parts by weight of long-chain aliphatic amines, such as tallow alkylamine, tallow alkylpropylene diamine, alkylhydroxypropylene diamine, dialkyl diethylene triamine, etc., per 100 parts by weight of pigment. By carrying out this process, various performances of the pigment composition obtained by the present invention in inks, paints, and other media are improved. The disazo pigment composition obtained by the method of the present invention as described above has a sharpness equivalent to that of the conventional disazo pigment, and the conventional disazo pigment and the disazo pigment prepared by the method described in the cited publication are more suitable for gravure. While the disazo pigment composition for ink has the above-mentioned drawbacks, the disazo pigment composition according to the present invention overcomes these drawbacks. The disazo pigments according to the invention are also greatly improved for use in paints and printing inks such as offset inks. In other words, when disazo pigments are used in paints or printing inks, the pigment is transferred from an aqueous pigment paste to an organic phase by a flushing method.
In conventional disazo pigments, particle growth of the pigment occurs during the flushing operation, resulting in a significant decrease in tinting power, but the disazo pigment composition according to the present invention does not have this drawback even if the operating temperature increases during flushing. This product produces printing inks and paints that are superior to the disazo pigment produced by the method described in the cited publication. Next, the present invention will be specifically explained with reference to Examples. Note that "%" or "%" in the text is based on weight unless otherwise specified. Example 1 Thirty parts of 3,3'-dichlorobenzidine is tetrazotized according to a conventional method to obtain a tetrazonium salt solution.
Separately, a soaking solution is prepared from 42.2 parts of acetoacetanilide and 3.0 parts of 4-acetoacetaminophenyl urea according to a conventional method. Both liquids are mixed and coupled, and the resulting pigment is filtered, washed with water, dried,
Grinding yielded 75.3 parts of the disazo pigment composition of the present invention. 14 parts of the pigment were added to 86 parts of lime rosin varnish (solid content: 40%) and dispersed using a paint conditioner to obtain 100 parts of gravure ink. When gravure printing was carried out on paper using this ink, printed matter was obtained which had a clear hue and significantly improved gloss and tinting power compared to when conventional disazo pigments were used. Example 2 5.3 parts of commercially available tallow alkylpropylene diamine was mixed with the coupling mixture in Example 1, and the pigment composition of the present invention was obtained in the same manner.
The pigment composition had further improved various performances than the pigment composition of the present invention obtained in Example 1. Example 3 The disazo of the present invention was prepared in the same manner as in Example 1 except that 46.7 parts of acetoaceto-P-toluidide and 1.8 parts of P-acetoacetaminophenyl urea were used in place of acetoacetanilide in Example 1. A pigment composition was obtained. The pigment composition, like that of Example 1, was excellent in various performances. Example 4 Example 1 was carried out in the same manner as in Example 1 except that an equimolar amount of acetoaceto-O-toluidide was used in place of acetoacetanilide in Example 1.
A disazo pigment composition similar to that in was obtained. Example 5 An offset ink was prepared using the pigment of the present invention in Example 1, and compared with a conventional offset ink using the same type of pigment, the results shown in Table 1 below were obtained.
【表】
変化
公知顔料３ 90 〃 25.3
上記第１表における公知顔料１は、未処理のピ
グメントエロー12であり、公知顔料２は実施例１
の４−アセトアセトアミノフエニル尿素に代え
て、２−アセトアセトアミノ安息香酸1.6部を用
いて他は実施例１と同様にして得た顔料（例えば
特公昭55−49087号公報）であり、公知顔料３は
上記の２−アセトアセトアミノ安息香酸に代えて
アセトアセトアニライド−２−メトキシ−５−カ
ルボアミド1.8部を用いたもの（特開昭53−41322
号公報参照）である。
また、性能の評価は、各顔料44.2部を含む含水
プレスケーキをオフセツトインキワニス300部に
加え、フラツシヤー中で60℃以下の温度で混和し
ながらフラツシングを行い、分離した水分を除去
してオフセツトインキを得、このインキを黒色の
アート紙上に展色したものを200℃で60秒間熱処
理して色調、着色力、透明度の変化を観測して耐
熱性を評価し、また、このインキを用いてスプレ
ツドメーター（東洋精機製、荷重（アクリル）
115ｇ、試料の容量0.5c.c.）でフロー値を測定し、
着色力は上部の各々のインキをチタン白インキで
稀釈して判定した。稀釈比率は下記の通りであ
る。
実施例１によるインキは14部の白インキで稀釈
公知顔料１によるインキは10部の白インキで稀
釈
公知顔料２、３によるインキは13部の白インキ
で稀釈[Table] Variable known pigments 3 90 〃 25.3
Known Pigment 1 in Table 1 above is untreated Pigment Yellow 12, and Known Pigment 2 is Example 1.
A pigment obtained in the same manner as in Example 1 except that 1.6 parts of 2-acetoacetaminobenzoic acid was used in place of 4-acetoacetaminophenyl urea (for example, Japanese Patent Publication No. 1987-49087), Known Pigment 3 uses 1.8 parts of acetoacetanilide-2-methoxy-5-carboxamide in place of the above-mentioned 2-acetoacetaminobenzoic acid (Japanese Unexamined Patent Publication No. 53-41322).
(see publication). In addition, performance evaluation was carried out by adding a water-containing press cake containing 44.2 parts of each pigment to 300 parts of offset ink varnish, performing flashing while mixing at a temperature of 60°C or less in a flasher, removing separated water, and removing the water. A set ink was obtained, this ink was spread on black art paper, heat treated at 200℃ for 60 seconds, changes in color tone, coloring power, and transparency were observed to evaluate heat resistance. Spread meter (manufactured by Toyo Seiki, load (acrylic))
115g, sample volume 0.5cc), measure the flow value,
Coloring strength was determined by diluting each of the upper inks with titanium white ink. The dilution ratio is as follows. The ink according to Example 1 is diluted with 14 parts of white ink. The ink with known pigment 1 is diluted with 10 parts of white ink. The ink with known pigments 2 and 3 is diluted with 13 parts of white ink.
Claims (1)
をアセトアセトアニライド系化合物にカツプリン
グさせてなるジスアゾ顔料において、上記アセト
アセトアニライド系化合物の約0.5〜20モル％が
下記の一般式（）で表わされる化合物で置換さ
れていることを特徴とするジスアゾ顔料組成物。 （但し、上記式中のR1は、１個または複数の水素
原子、メチル基、エチル基、メトキシ基、ニトロ
基、ハロゲン原子またはエトキシ基であり、R2
およびR3は水素原子、メチル基またはエチル基
であり、ｎは１または２である。）[Scope of Claims] 1. A disazo pigment prepared by coupling a tetrazotide of 3,3'-dichlorobenzidine with an acetoacetanilide compound, in which about 0.5 to 20 mol% of the acetoacetanilide compound is one of the following: A disazo pigment composition characterized in that it is substituted with a compound represented by the general formula (). (However, R 1 in the above formula is one or more hydrogen atoms, methyl group, ethyl group, methoxy group, nitro group, halogen atom or ethoxy group, and R 2
and R 3 is a hydrogen atom, a methyl group or an ethyl group, and n is 1 or 2. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10591783A JPS59232148A (en) | 1983-06-15 | 1983-06-15 | Disazo pigment composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10591783A JPS59232148A (en) | 1983-06-15 | 1983-06-15 | Disazo pigment composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59232148A JPS59232148A (en) | 1984-12-26 |
| JPS6129971B2 true JPS6129971B2 (en) | 1986-07-10 |
Family
ID=14420212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10591783A Granted JPS59232148A (en) | 1983-06-15 | 1983-06-15 | Disazo pigment composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59232148A (en) |
-
1983
- 1983-06-15 JP JP10591783A patent/JPS59232148A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59232148A (en) | 1984-12-26 |
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