JPH01104663A - Azo pigment composition for gravure ink - Google Patents
Azo pigment composition for gravure inkInfo
- Publication number
- JPH01104663A JPH01104663A JP62261383A JP26138387A JPH01104663A JP H01104663 A JPH01104663 A JP H01104663A JP 62261383 A JP62261383 A JP 62261383A JP 26138387 A JP26138387 A JP 26138387A JP H01104663 A JPH01104663 A JP H01104663A
- Authority
- JP
- Japan
- Prior art keywords
- strontium
- gravure ink
- pigment composition
- azo
- azo 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
- 239000000049 pigment Substances 0.000 title claims abstract description 46
- 239000000203 mixture Substances 0.000 title claims abstract description 19
- 229910052712 strontium Inorganic materials 0.000 claims abstract description 21
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims abstract description 17
- 159000000008 strontium salts Chemical class 0.000 claims abstract description 16
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 11
- 229920005989 resin Polymers 0.000 claims abstract description 11
- 239000011347 resin Substances 0.000 claims abstract description 11
- 239000004094 surface-active agent Substances 0.000 claims abstract description 11
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 10
- 229910052788 barium Inorganic materials 0.000 claims abstract description 9
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000987 azo dye Substances 0.000 claims abstract description 8
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 8
- 239000011575 calcium Substances 0.000 claims abstract description 8
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 5
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims description 12
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 10
- 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 claims description 10
- 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 claims description 10
- 229920002635 polyurethane Polymers 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000002932 luster Substances 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- -1 polyoxyethylene Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- DHEQXMRUPNDRPG-UHFFFAOYSA-N strontium nitrate Chemical compound [Sr+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O DHEQXMRUPNDRPG-UHFFFAOYSA-N 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- PZTQVMXMKVTIRC-UHFFFAOYSA-L chembl2028348 Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 PZTQVMXMKVTIRC-UHFFFAOYSA-L 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000010187 litholrubine BK Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940080350 sodium stearate Drugs 0.000 description 1
- WYPBVHPKMJYUEO-NBTZWHCOSA-M sodium;(9z,12z)-octadeca-9,12-dienoate Chemical compound [Na+].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O WYPBVHPKMJYUEO-NBTZWHCOSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- 229910001427 strontium ion Inorganic materials 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
【発明の詳細な説明】
〔発明の目的〕
（産業上の利用分野）
本発明は、有機溶剤型グラビアインキ適性、特にインキ
の流動性および貯蔵安定性ならびに乾燥皮膜の光沢およ
び鮮明性が優れたアゾ顔料組成物に関するものである。[Detailed Description of the Invention] [Object of the Invention] (Industrial Application Field) The present invention provides an ink that is suitable for organic solvent type gravure ink, particularly excellent fluidity and storage stability of the ink, and excellent gloss and clarity of the dry film. The present invention relates to an azo pigment composition.
（従来の技術）
２個以上の酸基を１分子中に含む１種または２種以上の
アゾ染料のカルシウムまたはバリウムレーキ顔料は、有
機溶剤型グラビアインキに使用された際。(Prior Art) When a calcium or barium lake pigment of one or more azo dyes containing two or more acid groups in one molecule is used in an organic solvent type gravure ink.
貯蔵時にインキの増粘あるいはゲル化、および色相の黄
変が起こり実用化が困難であった。当該問題の解決方法
として、各種樹脂や界面活性剤を顔料に表面処理する方
法が行なわれてきたが、これらの方法では、上記欠点を
解決するには至らなかった。During storage, the ink thickened or gelled, and the hue yellowed, making it difficult to put it to practical use. As a solution to this problem, methods have been used in which pigments are surface-treated with various resins or surfactants, but these methods have not been able to solve the above-mentioned drawbacks.
（発明が解決しようとする問題点）
２個以上の酸基を１分子中に含む１種または２種以上の
アゾ染料のカルシウムまたはバリウムレーキ顔料は、１
個の酸基を１分子中に含むものと異なり。(Problems to be Solved by the Invention) Calcium or barium lake pigments of one or more azo dyes containing two or more acid groups in one molecule are
Unlike those containing 1 acid group in 1 molecule.
有機溶剤型グラビアインキでのレオロジー的特性が特に
劣っており、貯蔵時の変色が激しい。The rheological properties of organic solvent-based gravure inks are particularly poor, and the color changes significantly during storage.
本発明は、有機溶剤型グラビアインキの使用適性に有効
なアゾ顔料組成物に関するものである。The present invention relates to an azo pigment composition that is suitable for use in organic solvent type gravure inks.
（問題点を解決するための手段）
本発明は、カルボン酸基またはスルホン酸基を１分子中
に２個以上含む１種または２種以上のアゾ染料のストロ
ンチウム以外のアルカリ土類金属レーキ顔料（Ｉ）、な
らびにストロンチウムアゾレーキ顔料（ＩＩ）、界面活
性剤の難溶性ストロンチウム塩（ＩＩＩ）または樹脂の
ストロンチウム（ＩＶ）を含有する有機溶剤型グラビア
インキ用のアゾ顔料組成物である。(Means for Solving the Problems) The present invention provides alkaline earth metal lake pigments other than strontium of one or more azo dyes containing two or more carboxylic acid groups or sulfonic acid groups in one molecule ( I), as well as a strontium azo lake pigment (II), a sparingly soluble strontium salt (III) as a surfactant, or a strontium (IV) resin as an azo pigment composition for an organic solvent type gravure ink.
なお、カルシウム、バリウムまたはストロンチウムを使
用したアゾレーキ顔料は公知であるが、それぞれでは、
鮮明性、光沢、流動性および耐水性が不十分である。Incidentally, azo lake pigments using calcium, barium or strontium are known, but in each case,
Poor clarity, gloss, fluidity and water resistance.
本発明においてストロンチウム塩を含有させる方法は、
以下に示す１例のように、顔料製造と同時に形成させる
方法および混合する方法の２通りある。In the present invention, the method for containing strontium salt is as follows:
As shown in one example below, there are two methods: a method of forming at the same time as pigment production and a method of mixing.
（ａ）アルカリ土類金属イオンと難溶性塩を形成する水
溶性の界面活性剤（Ｖ）の存在下、酸基（カルボん酸基
またはスルホン酸基）を１分子中に２個以上含むストロ
ンチウム以外のアルカリ土類金属１例えばカルシウムま
たはバリウムレーキ顔料（Ｉ）を生成させ、その後、ス
トロンチウムイオンを加えて。(a) Strontium containing two or more acid groups (carboxylic acid group or sulfonic acid group) in one molecule in the presence of a water-soluble surfactant (V) that forms a poorly soluble salt with an alkaline earth metal ion. Alkaline earth metals other than 1 such as calcium or barium lake pigments (I) are formed and then strontium ions are added.
カルシウムまたはバリウムイオンの一部とストロンチウ
ムイオンとのイオン交換を行なわせるか、あるいはスト
ロンチウムイオンを加えた後、カルシウムまたはバリウ
ムイオンを加える事により、カルシウムまたはバリウム
、およびストロンチウムのアゾレーキ顔料（Ｉおよび■
）と、界面活性剤（Ｖ）のカルシウムまたはバリウム、
およびストロンチウムの難溶性塩（ＩＩＩ）の混合物を
生成させる。Calcium or barium and strontium azo lake pigments (I and
) and surfactant (V) calcium or barium,
and a poorly soluble salt of strontium (III).
（ｂ）酸基（カルボン酸基またはスルホン酸基）を１分
子中に２個以上含むアゾ染料のストロンチウム以外のア
ルカリ土類金属１例えばカルシラｌ、または。(b) Alkaline earth metals other than strontium 1, such as calcilyl, or azo dyes containing two or more acid groups (carboxylic acid groups or sulfonic acid groups) in one molecule.
バリウムレーキ顔料（Ｉ）と、ストロンチウムアゾレー
キ顔料（ＩＩ）、界面活性剤（Ｖ）の難溶性ストロンチ
ウム塩（■）、または樹脂（Ｖｌ）のストロランチラム
塩（ＩＶ）とを混合する。混合方法としては。The barium lake pigment (I) is mixed with the strontium azo lake pigment (II), the sparingly soluble strontium salt (■) of the surfactant (V), or the strontium salt (IV) of the resin (Vl). As for the mixing method.
乾式で混合するか、 （Ｉ）の顔料スラリーに（ｎ）な
いしくＩＶ）を添加し攪拌する事により混合される。They can be mixed in a dry manner, or by adding (n) or IV) to the pigment slurry of (I) and stirring.
本発明において、酸基を１分子中に２個以上含むアブ染
料のストロンチウム以外のアルカリ土類金属レーキ顔料
（Ｉ）は１例えばＣ，１，１５８２５：１、Ｃ，！、１
５８２５１．Ｃ，１，１５８５ｏａｔ、ｃ、１．１５８
５０：２．ｃ、１．１５８ｅｓ：ｔ、ｃ、１．１５８６
５：２．ｃ、１．１６１０５：１などである。ストロン
チウムアゾレーキ顔料（ＩＩ）は、 （Ｉ）のアゾ染料
のストロンチウムレーキ顔料、または１分子中の酸基の
数が１個のアゾ染料のストロウチウムレーキ顔料であっ
てもよい。In the present invention, the alkaline earth metal lake pigment (I) other than strontium, which is an ab dye containing two or more acid groups in one molecule, is 1, for example, C, 1, 15825: 1, C,! ,1
58251. C, 1,1585 oat, c, 1.158
50:2. c, 1.158es: t, c, 1.1586
5:2. c, 1.16105:1, etc. The strontium azo lake pigment (II) may be the azo dye strontium lake pigment of (I) or the azo dye strontium lake pigment having one acid group per molecule.
界面活性剤の難溶性ストロンチウム塩（ＩＩＩ）の界面
活性剤（Ｖ）は２例えば、マルセル石けん、リノール酸
ナトリウム、ステアリン酸ナトリウム、ラウリル硫ｔａ
アンモニウム、ポリオキシエチレンアルキルフェノール
エーテル硫酸ナトリウム、ナフタレンスルホン酸ホルマ
リン縮合物ナトリウム塩、ドデシルベンゼンスルホン酸
ナトリウム、アルキルナフタレンスルホン酸ナトリウム
、ポリカルボン酸型高分子活性剤などが挙げられる。樹
脂のストロンチウム塩（ＩＶ）の樹脂（Ｖｌ）は１例え
ば、ガムロジン、重合ロジン、不均化ロジン、水添ロジ
ン、マレイン化ロジン、硬化ロジン、フタル酸アルキッ
ド樹脂などである。The surfactant (V) of the sparingly soluble strontium salt (III) of the surfactant is 2. For example, Marcel soap, sodium linoleate, sodium stearate, lauryl sulfate.
Examples include ammonium, sodium polyoxyethylene alkylphenol ether sulfate, naphthalene sulfonic acid formalin condensate sodium salt, sodium dodecylbenzenes sulfonate, sodium alkylnaphthalene sulfonate, polycarboxylic acid type polymer activators, and the like. Examples of the resin (Vl) of the strontium salt (IV) of the resin include gum rosin, polymerized rosin, disproportionated rosin, hydrogenated rosin, maleated rosin, hardened rosin, phthalate alkyd resin, and the like.
なお、 （ＩＩ）ないしくＩＶ）は、（Ｉ）に対し０．
５〜３０重量％、好ましくは１〜２０重量％含有させる
。In addition, (II) or IV) is 0.0 compared to (I).
The content is 5 to 30% by weight, preferably 1 to 20% by weight.
本発明において、グラビアインキとしては、ライムロジ
ン系、ニトロセルロース系、ポリアミド系環化ゴム系、
塩化ゴム系、塩化ビニル系などがあり。In the present invention, examples of the gravure ink include lime rosin-based, nitrocellulose-based, polyamide-based cyclized rubber-based,
There are chlorinated rubber types, vinyl chloride types, etc.
特にウレタン系において適性が優れている。また。It is particularly suitable for urethane systems. Also.
有機溶剤としては、トルエン、メチルエチルケトン。Examples of organic solvents include toluene and methyl ethyl ketone.
酢酸エチル、イソプロピルアルコール、エタノールなど
の１種または２種以上である。One or more of ethyl acetate, isopropyl alcohol, ethanol, etc.
（作 用）
本１発明において（ＩＩ）、 （ＩＩＩ）または（Ｉ
Ｖ）のストロンチウム塩は、ストロンチウム以外のアゾ
レーキ顔料（Ｉ）が、インキ中の樹脂および水と配位結
合する事に伴って貯蔵時にインキの増粘あるいはゲル化
、および色相の黄変が引き起こされるのを防止する機能
を持つものと考えられる。すなわち、インキ中において
樹脂との反応性を低下させる作用、および顔料自体の水
との反応性を低下させる事により伴う耐水性付与の作用
を有すると考えられる。(Function) In the present invention 1, (II), (III) or (I
The strontium salt (V) causes thickening or gelation of the ink and yellowing of the hue during storage as the azo lake pigment (I) other than strontium coordinates with the resin and water in the ink. It is thought that it has the function of preventing this. That is, it is thought to have the effect of reducing the reactivity with the resin in the ink, and the effect of imparting water resistance by reducing the reactivity of the pigment itself with water.
（実施例）
以下、実施例により本発明を説明する。例中１部とは重
量部を１％とは重量％をそれぞれ表わす。(Example) The present invention will be explained below with reference to Examples. In the examples, 1 part means part by weight, and 1% means % by weight.
実施例１
４−アミノトルエン−３−スルホンａａｏ部ｔ−水４０
０部および水酸化ナトリウム７部とともに室温で１０分
間攪拌し、完全に溶解させる。３５％塩酸４０部を加え
、酸性化した後、氷２００部を加え。Example 1 4-aminotoluene-3-sulfone aao part t-water 40
Stir with 0 parts of sodium hydroxide and 7 parts of sodium hydroxide for 10 minutes at room temperature to ensure complete dissolution. Add 40 parts of 35% hydrochloric acid to acidify the mixture, and then add 200 parts of ice.
３℃以下に冷却し、水４０部に溶解した亜硝酸ソーダ１
２部を加えてジアゾ化した。Sodium nitrite cooled to below 3°C and dissolved in 40 parts of water
Two parts were added to diazotize.
β−オキシナフトエ酸３３部を水６００部、水酸化ナト
リウム１５部および炭酸ナトリウム９部とともに室温で
６０分間攪拌し、完全に溶解させたちのをカップラー成
分とした。このカップラー成分に上記ジアゾ成分を１５
分要し滴下した後、更に１時間攪拌を続け、カップリン
グ反応を完結させた。なお。33 parts of β-oxynaphthoic acid was stirred with 600 parts of water, 15 parts of sodium hydroxide, and 9 parts of sodium carbonate at room temperature for 60 minutes to completely dissolve the mixture, which was then used as a coupler component. Add 15% of the above diazo component to this coupler component.
After the dropwise addition took several minutes, stirring was continued for an additional hour to complete the coupling reaction. In addition.
カップリング液のＰＨは８．５であった。その後、ステ
アリン酸ナトリウム８部を加え３０分間攪拌後。The pH of the coupling liquid was 8.5. Then, 8 parts of sodium stearate was added and stirred for 30 minutes.
２０％塩化ストロンチウム水溶液１００部を加え。Add 100 parts of 20% strontium chloride aqueous solution.
８０℃に加熱して３０分間攪拌した。濾過・水洗後。The mixture was heated to 80°C and stirred for 30 minutes. After filtration and washing.
熱風循環型オーブン中８０℃で一夜乾燥し、赤色顔料８
０部を得た。Dry overnight at 80°C in a hot air circulation oven, red pigment 8
I got 0 copies.
実施例１に準じて表−１のようなジアゾ成分およびカッ
プラー成分を反応させ２次に界面活性剤（比較例では樹
脂）およびアルカリ土類金属塩を添加し顔料を得た。A diazo component and a coupler component as shown in Table 1 were reacted according to Example 1, and then a surfactant (resin in the comparative example) and an alkaline earth metal salt were added to obtain a pigment.
実施例１，２および３．かつ比較例１および２で得られ
た顔料についての試験を次のようにして行なった。Examples 1, 2 and 3. The pigments obtained in Comparative Examples 1 and 2 were tested as follows.
顔料１０部を、ポリウレタングラビアフェス（ウレタン
樹脂）９０部の中で、１５０部のアルミナ・ビーズを使
用したペイント・コンディショナーで分散した。得られ
たインキの取り出し時および室温１５日後の粘度２色相
の鮮明性、ならびに光沢の結果を表−３に示した。また
１分散インキ１００部、シンナー（トルエン、メチルエ
チルケトン混合系）３５部および水５部を混和したもの
と２分散インキ１００部およびシンナー（トルエン、メ
チルエチルケトン混合系）４０部を混和したものとの５
０℃、７日後の色差を測定し顔料の耐水性の指標（色差
小−耐水性大）とした。結果は２表−３に示した。Ten parts of pigment were dispersed in a paint conditioner using 150 parts of alumina beads in 90 parts of polyurethane gravure face (urethane resin). Table 3 shows the results of the viscosity, two-hue clarity, and gloss of the obtained ink when it was taken out and after 15 days at room temperature. In addition, 100 parts of 1-dispersion ink, 35 parts of thinner (toluene and methyl ethyl ketone mixed system) and 5 parts of water were mixed together, and 5 parts of 2-dispersion ink and 40 parts of thinner (toluene and methyl ethyl ketone mixed system) were mixed together.
The color difference after 7 days at 0°C was measured and used as an index of the water resistance of the pigment (small color difference - high water resistance). The results are shown in Table 2-3.
実施例４
０ジンソーダと硝酸ストロンチウムの反応生成物である
ロジンストロンチウム１部をブリリアントカーミツ６８
，９部に■型混合機で乾式混合した顔料組成物、および
混合しない従来顔料（比較例３）について、実施例１と
同様に試験した結果を表−３に示した。Example 4 One part of rosin strontium, which is a reaction product of rosin soda and strontium nitrate, was added to brilliant carmite 68
Table 3 shows the results of tests conducted in the same manner as in Example 1 for a pigment composition dry-mixed with 9 parts of .
実施例５
ｌ−（３’−力ルボキシ−２′−ヒドロキシナフチル）
アゾベンゼン−２−カルボン酸ストロンチウムを、ブリ
リアントカーミン６Ｂのスラリー（顔料含有率５％）に
、固形分重量比で１／９となるように混合した顔料組成
物を得た。Example 5 l-(3'-hydroxy-2'-hydroxynaphthyl)
A pigment composition was obtained by mixing strontium azobenzene-2-carboxylate into a slurry of brilliant carmine 6B (pigment content: 5%) at a solid content weight ratio of 1/9.
得られたアゾ顔料組成物について、実施例１と同様に試
験した結果を表−３に示した。The obtained azo pigment composition was tested in the same manner as in Example 1, and the results are shown in Table 3.
実施例１に準じて表−２のような顔料９部、およびスト
ロンチウム塩１部からなる本発明顔料組成物（実施例６
および７）についてもストロンチウム塩を混合しない従
来顔料（比較例４および５）とともに、実施例１と同様
にして試験した。According to Example 1, a pigment composition of the present invention (Example 6) consisting of 9 parts of the pigment shown in Table 2 and 1 part of strontium salt
and 7) were also tested in the same manner as in Example 1, along with conventional pigments (Comparative Examples 4 and 5) in which no strontium salt was mixed.
結果は２表−３に示した。The results are shown in Table 2-3.
ポリウレタングラビアインキ試験同様、実施例１〜７．
比較例１〜５で得られた顔料についてのポリアミドグラ
ビアインキ試験および環化ゴムグラビアインキ試験の結
果を表−４および５に示した。Similar to the polyurethane gravure ink test, Examples 1 to 7.
The results of the polyamide gravure ink test and the cyclized rubber gravure ink test for the pigments obtained in Comparative Examples 1 to 5 are shown in Tables 4 and 5.
試験条件は以下のとおりである。The test conditions are as follows.
本発明により次の効果が確認された。 The following effects were confirmed by the present invention.
（Ｉ）グラビアインキ、特にポリウレタン系で、流動性
、貯蔵安定性が著しく向上した。(I) Fluidity and storage stability of gravure inks, especially polyurethane inks, were significantly improved.
（２）グラビアインキ、特にポリウレタン系で乾燥皮膜
の色相の鮮明性、光沢が著しく向上した。(2) With gravure inks, especially polyurethane inks, the hue clarity and gloss of the dried film were significantly improved.
Claims (1)
アゾ染料のストロンチウム以外のアルカリ土類金属レー
キ顔料（ I ）、ならびにストロンチウムアゾレーキ顔
料（II）、界面活性剤の難溶性ストロンチウム塩（III
）または樹脂のストロンチウム塩（IV）を含有する有機
溶剤型グラビアインキ用アゾ顔料組成物。 ２、上記（ I ）のアルカリ土類金属がカルシウムまた
はバリウムである特許請求の範囲第１項記載の有機溶剤
型グラビアインキ用アゾ顔料組成物。 ３、上記（III）の界面活性剤がアニオン活性剤である
特許請求の範囲第１項または第２項記載の有機溶剤型グ
ラビアインキ用アゾ顔料組成物。 ４、上記（IV）の樹脂がロジンである特許請求の範囲第
１項〜第３項いずれか記載の有機溶剤グラビアインキ用
アゾ顔料組成物。 ５、上記（ I ）に対し上記（II）ないし（IV）を１〜
２０重量％用いる特許請求の範囲第１項〜第４項いずれ
か記載の有機溶剤型グラビアインキ用アゾ顔料組成物。 ６、グラビアインキがポリウレタングラビアインキであ
る特許請求の範囲第１項〜第５項いずれか記載の有機溶
剤型グラビアインキ用アゾ顔料組成物。[Scope of Claims] 1. Alkaline earth metal lake pigments other than strontium which are azo dyes having two or more carboxylic acid groups or sulfonic acid groups (I), strontium azo lake pigments (II), and problems with surfactants Soluble strontium salt (III
) or an azo pigment composition for organic solvent type gravure ink containing a strontium salt (IV) of a resin. 2. The azo pigment composition for organic solvent type gravure ink according to claim 1, wherein the alkaline earth metal in (I) is calcium or barium. 3. The azo pigment composition for organic solvent type gravure ink according to claim 1 or 2, wherein the surfactant (III) is an anionic surfactant. 4. The azo pigment composition for organic solvent gravure ink according to any one of claims 1 to 3, wherein the resin (IV) is rosin. 5. For (I) above, set (II) to (IV) above from 1 to
An azo pigment composition for organic solvent type gravure ink according to any one of claims 1 to 4, which is used in an amount of 20% by weight. 6. The azo pigment composition for organic solvent type gravure ink according to any one of claims 1 to 5, wherein the gravure ink is a polyurethane gravure ink.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62261383A JPH0822985B2 (en) | 1987-10-16 | 1987-10-16 | Azo pigment composition for gravure ink |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62261383A JPH0822985B2 (en) | 1987-10-16 | 1987-10-16 | Azo pigment composition for gravure ink |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01104663A true JPH01104663A (en) | 1989-04-21 |
| JPH0822985B2 JPH0822985B2 (en) | 1996-03-06 |
Family
ID=17361087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62261383A Expired - Fee Related JPH0822985B2 (en) | 1987-10-16 | 1987-10-16 | Azo pigment composition for gravure ink |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0822985B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5380363A (en) * | 1992-02-13 | 1995-01-10 | Francolor Pigments Sa | Pigment composition |
| JP2007302654A (en) * | 2006-04-12 | 2007-11-22 | Lab Servier | New strontium salt of sulfonic acid, method for producing the same, and pharmaceutical composition containing the same |
| CN114945637A (en) * | 2019-12-20 | 2022-08-26 | Dic株式会社 | Pigment composition, active energy ray-curable offset ink, and method for producing pigment composition |
| WO2022209690A1 (en) * | 2021-04-01 | 2022-10-06 | Dic株式会社 | Pigment composition and ink using same |
-
1987
- 1987-10-16 JP JP62261383A patent/JPH0822985B2/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5380363A (en) * | 1992-02-13 | 1995-01-10 | Francolor Pigments Sa | Pigment composition |
| JP2007302654A (en) * | 2006-04-12 | 2007-11-22 | Lab Servier | New strontium salt of sulfonic acid, method for producing the same, and pharmaceutical composition containing the same |
| JP4584952B2 (en) * | 2006-04-12 | 2010-11-24 | レ ラボラトワール セルヴィエ | Novel strontium salt of sulfonic acid, process for its preparation and pharmaceutical composition containing it |
| CN114945637A (en) * | 2019-12-20 | 2022-08-26 | Dic株式会社 | Pigment composition, active energy ray-curable offset ink, and method for producing pigment composition |
| CN114945637B (en) * | 2019-12-20 | 2023-10-13 | Dic株式会社 | Pigment composition, active energy ray-curable offset ink, and method for producing pigment composition |
| WO2022209690A1 (en) * | 2021-04-01 | 2022-10-06 | Dic株式会社 | Pigment composition and ink using same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0822985B2 (en) | 1996-03-06 |
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