JPH0552867B2 - - Google Patents
Info
- Publication number
- JPH0552867B2 JPH0552867B2 JP22356784A JP22356784A JPH0552867B2 JP H0552867 B2 JPH0552867 B2 JP H0552867B2 JP 22356784 A JP22356784 A JP 22356784A JP 22356784 A JP22356784 A JP 22356784A JP H0552867 B2 JPH0552867 B2 JP H0552867B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- dye
- formula
- parts
- group
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 claims description 34
- 239000000975 dye Substances 0.000 claims description 33
- 239000001000 anthraquinone dye Substances 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000000987 azo dye Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- -1 nitride compound Chemical class 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 230000002335 preservative effect Effects 0.000 description 4
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 2
- 229960000943 tartrazine Drugs 0.000 description 2
- 235000012756 tartrazine Nutrition 0.000 description 2
- 239000004149 tartrazine Substances 0.000 description 2
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 2
- 229950006389 thiodiglycol Drugs 0.000 description 2
- NJPMVPIVCWCXMG-UHFFFAOYSA-N 1,4-diamino-9,10-dioxo-3-phenoxyanthracene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=C(N)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 NJPMVPIVCWCXMG-UHFFFAOYSA-N 0.000 description 1
- GMBNNHLANOGOAU-UHFFFAOYSA-N 1-amino-4-(cyclohexylamino)-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC1CCCCC1 GMBNNHLANOGOAU-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- UDCKXEFJOHLCKM-UHFFFAOYSA-N 5-amino-4-hydroxy-3-phenyldiazenylnaphthalene-2,7-disulfonic acid Chemical compound OC1=C2C(N)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=C1N=NC1=CC=CC=C1 UDCKXEFJOHLCKM-UHFFFAOYSA-N 0.000 description 1
- ZPRUFNWBYQKDGT-UHFFFAOYSA-N 7-amino-4-hydroxy-3-[(4-methoxy-2-sulfophenyl)diazenyl]naphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC(OC)=CC=C1N=NC1=C(O)C2=CC=C(N)C=C2C=C1S(O)(=O)=O ZPRUFNWBYQKDGT-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- DHQJMKJYFOHOSY-UHFFFAOYSA-L disodium 4-amino-3-[[4-[4-[(2,4-diaminophenyl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]-5-oxido-6-phenyldiazenyl-7-sulfonaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Cc1cc(ccc1N=Nc1ccc(N)cc1N)-c1ccc(N=Nc2c(N)c3c(O)c(N=Nc4ccccc4)c(cc3cc2S([O-])(=O)=O)S([O-])(=O)=O)c(C)c1 DHQJMKJYFOHOSY-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 230000003449 preventive effect Effects 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
本発明は、水性インキ組成物に関するものであ
つて、その主な目的は、筆記具用、印刷用及び記
録用として好適な耐水性等を有する水性インキ組
成物を提供するにある。
従来、筆記具等に用いられる水性インキ組成物
は、公知の如く、一般の水溶性染料の水及びグリ
コール系溶剤等と混合したものであつたが、この
種の従来の水性インキ組成物は、筆記具用、印刷
用及び記録用として、耐水性、耐光性及び金属に
対する耐腐蝕性等において不十分であつた。
すなわち、従来水性インキ組成物は、まず第１
に、紙のセルローズと水溶性染料との親和力が少
ないために、筆記途中の書類あるいは筆記直後の
書類の上に水分がかかつた場合には、インキがに
じんで字が不明瞭になり、書類が汚損されるとい
う欠点を有していた。この場合において、耐水性
向上の方策として浸透剤、活性剤等を添加して使
用する方法が考えられるが、染料構造に起因する
本質的な劣性のために、失張り充分な効果を挙げ
得ないといううらみがある。
次に、従来の水性インキ組成物による筆記物
は、太陽光線に当たつた場合に、色の変化・汚損
が大きかつた。更に、酸性の水溶性染料を使用し
た場合には、金属に対する腐蝕性が激しくて変
色、目詰り等の原因となつた。
本発明者は、如上の問題点を解決すべく種々検
討を行い、親和見を提案してきたが（特公昭59−
28590）、さらに研究を鋭意続行した結果、一般式
［式〔〕中、
D1は、遊離酸の形において次式〔〕
（式〔〕中、
ｎは１又は２を示し、
Ｚは、
Arまたは
The present invention relates to an aqueous ink composition, and its main purpose is to provide an aqueous ink composition having water resistance suitable for use in writing instruments, printing, and recording. Conventionally, water-based ink compositions used for writing instruments, etc. have been made by mixing general water-soluble dyes with water, glycol solvents, etc.; For use in applications such as printing, recording, and recording, water resistance, light resistance, and corrosion resistance against metals were insufficient. That is, conventional water-based ink compositions first
In addition, because the cellulose in paper has a low affinity for water-soluble dyes, if moisture falls onto a document that is in the process of being written on or has just been written on, the ink will smear and the writing will become unclear, causing the document to deteriorate. It had the disadvantage that it was contaminated. In this case, a method of adding penetrants, activators, etc. may be considered as a measure to improve water resistance, but due to the inherent recessiveness caused by the dye structure, it is not possible to achieve a sufficient effect of destretching. There is a feeling of resentment. Next, writing materials made with conventional water-based ink compositions were subject to large color changes and staining when exposed to sunlight. Furthermore, when acidic water-soluble dyes are used, they are highly corrosive to metals, causing discoloration and clogging. The present inventor has conducted various studies to solve the above problems and has proposed a compatible approach (Tokuko Kokō Sho 59-
28590), and as a result of further research, the general formula [Formula [], D 1 is the following formula [] in the free acid form: (In formula [], n represents 1 or 2, Z is Ar or
【式】を示す。
但し、Arは、メトキシ基、スルホン基及びハ
ロゲンからなる群から選ばれた１の置換基或は同
種又は別種の２の置換基によつて置換されたベン
ゼン系のジアゾ成分残基を示し、
Ｘ及びＹは、互いに独立して水素、メチル基又
はメトキシ基を示す。）
で表わされるアミノ基を有する水溶性アゾ染料残
基または水溶性アントラキノン染料残基を示し、
Ｒは、下記式乃至で表わされる基からなる群
から選ばれた活性水素を有する水溶性窒化化合物
の残基を示し、
−NHC2H4NHC3H6Si（OH）3
D2は、式〔〕で表わされるアミノ基を有す
る水溶性アゾ染料残基、水溶性アントラキノン染
料残基、または上記Ｒを示す。］
で表わされる染料を含有させることにより、色調
鮮明で、且つ優れた耐水性及び耐光性を有し、金
属に対する腐蝕性もないところの、極めて優れた
性能を有する水性インキ組成物が得られることを
見いだし、本発明を完成したものである。
本発明に用いられる一般式（）で表される染
料は、常法により、溶媒中、塩化シアヌールとア
ミノ基を有する水溶性アゾまたはアントラキノン
染料及び下記の活性水素を有する水溶性窒素化合
物
NH2C2H4NHC3H6Si（OH）3
を逐次反応することにより得られる。
アミノ基を有する水溶性アゾまたはアントラキ
ノン染料の例としては、５−アミノ−４−ヒドロ
キシ−３−フエニルアゾ−２，７−ナフタレンジ
スルホン酸、５−アミノ−４−ヒドロキシ−３−
（ｏ−メトキシフエニルアゾ）−２，７−ナフタレ
ンジスルホン酸、７−アミノ−４−ヒドロキシ−
３−（４−メトキシ−２−スルホフエニルアゾ）−
２−ナフタレンスルホン酸、６−アミノ−４−ヒ
ドロキシ−３−（ｏ−スルホフエニルアゾ）−２、
７−ナフタレンジスルホン酸、５−アミノ−４−
ヒドロキシ−３−（４−クロルフエニルアゾ）−
２，７−ナフタレンジスルホン酸、５−アミノ−
４−ヒドロキシ−３−（３，６−ジクロルフエニ
ルアゾ）−２，７−ナフタレンジスルホン酸、２
−〔４−（１−ヒドロキシ−６−アミノ−３−スル
ホ−２−ナフチルアゾ）−５−メトキシ−２−メ
チルフエニルアゾ〕−３−ベンゼンスルホン酸、
１−アミノ−４−シクロヘキシルアミノ−２−ア
ントラキノンスルホン酸、１，４−ジアミノ−２
−フエノキシ−３−アントラキノンスルホン酸等
が挙げられる。これらの染料及び化合物は、単独
または複数で用いることが出来る。
本発明に係る一般式（）で表される染料を、
遊離酸の形で具体的に例示すると、以下の通りで
ある。なお、該染料は、所望のアルカリでアルカ
リ塩とすることにより、溶解性のよい水溶性染料
が得られる。この場合におけるアルカリ源には、
水酸化ナトリウム、水酸化カリウム、水酸化リチ
ウム、アンモニア水等が用いられる。[Formula] is shown. However, Ar represents a benzene-based diazo component residue substituted with one substituent selected from the group consisting of a methoxy group, a sulfone group, and a halogen, or two substituents of the same type or different types, and Y each independently represent hydrogen, a methyl group or a methoxy group. ) represents a water-soluble azo dye residue or a water-soluble anthraquinone dye residue having an amino group,
R represents a residue of a water-soluble nitride compound having active hydrogen selected from the group consisting of groups represented by the following formulas, −NHC 2 H 4 NHC 3 H 6 Si(OH) 3 D 2 represents a water-soluble azo dye residue having an amino group represented by the formula [], a water-soluble anthraquinone dye residue, or the above R. ] By containing the dye represented by the following, it is possible to obtain an aqueous ink composition with extremely excellent performance, which has a clear color tone, excellent water resistance and light resistance, and is not corrosive to metals. They discovered this and completed the present invention. The dye represented by the general formula () used in the present invention is prepared by adding cyanuric chloride, a water-soluble azo or anthraquinone dye having an amino group, and a water-soluble nitrogen compound having the following active hydrogen in a solvent in a conventional manner. NH2C2H4NHC3H6Si ( OH ) 3 _ It is obtained by sequentially reacting. Examples of water-soluble azo or anthraquinone dyes having an amino group include 5-amino-4-hydroxy-3-phenylazo-2,7-naphthalenedisulfonic acid, 5-amino-4-hydroxy-3-
(o-methoxyphenylazo)-2,7-naphthalenedisulfonic acid, 7-amino-4-hydroxy-
3-(4-methoxy-2-sulfophenylazo)-
2-naphthalenesulfonic acid, 6-amino-4-hydroxy-3-(o-sulfophenylazo)-2,
7-naphthalenedisulfonic acid, 5-amino-4-
Hydroxy-3-(4-chlorophenylazo)-
2,7-naphthalenedisulfonic acid, 5-amino-
4-Hydroxy-3-(3,6-dichlorophenylazo)-2,7-naphthalenedisulfonic acid, 2
-[4-(1-hydroxy-6-amino-3-sulfo-2-naphthylazo)-5-methoxy-2-methylphenylazo]-3-benzenesulfonic acid,
1-amino-4-cyclohexylamino-2-anthraquinone sulfonic acid, 1,4-diamino-2
-phenoxy-3-anthraquinone sulfonic acid and the like. These dyes and compounds can be used alone or in combination. The dye represented by the general formula () according to the present invention is
Specific examples in the form of free acids are as follows. Note that by converting the dye into an alkali salt with a desired alkali, a water-soluble dye with good solubility can be obtained. The alkaline source in this case is
Sodium hydroxide, potassium hydroxide, lithium hydroxide, ammonia water, etc. are used.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
本発明に係る水性インキ組成物は、一般式
（）で表される染料を、水及び水溶性有機溶剤、
並びに必要に応じて水溶性界面活性剤、水溶性樹
脂及び添加剤等と混合して調製される。
一般式（）の染料と混合される前記水溶性有
機溶剤としては、エチレングリコール、ジエチレ
ングリコール、プロピレングリコール、チオジグ
リコール等のグリコール系溶剤、セロソルフ系溶
剤、アルコール系溶剤、カルビトール系溶剤、ア
ルカノールアミン等が挙げられる。また、必要に
応じて一般式（）の染料と混合される前記水溶
性界面活性剤としては、Ｎ−アルキルピロリド
ン、ビニルピロリドン誘導体、アニオン系界面活
性剤、非イオン系界面活性剤、両性界面活性剤等
が挙げられる。更に、必要に応じて一般式（）
の染料と混合される水溶性樹脂としては、天然又
は合成の水溶性樹脂が挙げられ、また、添加剤と
しては、PH調整剤、防腐剤、防錆剤または金属封
鎖剤等を用いることもできる。
以上の如くして得られる多様な色彩の本発明水
性インキ組成物は、色調鮮明で、且つ優れた耐水
性及び耐光性を有し、金属に対する腐蝕性もな
く、また他色の補色用としても優れた性能を有
し、筆記具用インキ、スタンプ用インキ、ジエツ
ト印刷用インキ、記録計用インキ等として最適で
ある。
以上に本発明の実施例を示す。なお、重量部を
部と略して記載する。
実施例 １
染料例(1)の染料（Na塩） ５部
エチレングリコール 10部
ジエチレングリコール 10部
チオジグリコール ５部
ブチルセロソルブ 0.5部
アニオン系界面活性剤（商品名：ハイテノール
08） 0.2部
防腐剤 0.5部
蒸溜水 68.5部
上記配合物を60〜70℃にて混合・溶解させた
後、工業用ろ紙でろ過して本発明に係る黒色水性
インキ組成物を調製した。
得られたインキ組成物をサインペン容器にセツ
トし、筆記テストを行つたところ、ペン先部分で
のインキのかすれがなく、常時円滑にインキが流
出し、筆跡は色調鮮明で、且つ優れた耐水性及び
耐光性を有していた。
実施例 ２
染料例(2)の染料（Li塩）５部を実施例１に用い
た染料の代りに使用して、爾余の点においては実
施例１の場合と同様にして、本発明に係る赤色水
性インキ組成物を得た。
得られたインキ組成物は、実施例１の組成物と
同様、優れた性能を有していた。
実施例 ３
染料例(6)の染料（Na塩） ８部
エチレングリコール 10部
ジエチレングリコール 10部
プロピレングリコール ５部
アニオン系界面活性剤（商品系：ハイテノール
08） 0.2部
防腐剤 0.5部
蒸溜水 66.3部
上記配合物を実施例１の場合と同様に処理し
て、本発明に係る茶色水性インキ組成物を得た。
得られたインキ組成物は、実施例１の組成物と
同様、優れた性能を有していた。
実施例 ４
染料例(7)の染料（Na塩）８部を実施例３に用
いた染料の代りに使用して、爾余の点においては
実施例３の場合と同様にして、本発明に係る黒色
水性インキ組成物を得た。
得られたインキ組成物は、実施例１の組成物と
同様、優れた性能を有していた。
比較例 １
実施例１に用いた染料の代りにタートラジン
（C.I.Acid Yellow23）５部を使用して、爾余の
点においては実施例１の場合と同様として、黄色
水性インキ組成物を調製した。
比較例 ２
実施例２に用いた染料の代りにニユーコクシン
（C.I.Acid Red18）５部を使用して、爾余の点に
おいては実施例２の場合と同様にして、赤色水性
インキ組成物を調製した。
比較例 ３
実施例３に用いた染料の代りにWater Brown
＃16〔オリエント化学工業社製、タートラジン、
ニユーコクシン、水溶性鋼フタロシアニン（C.I.
Direct Blue87）の配合品〕８部を使用して、爾
余の点においては実施例３の場合と同様にして、
茶色水性インキ組成物を調製した。
比較例 ４
実施例４に用いた染料の代りにC.I.ダイレクト
ブラツク154 ３部を使用して、爾余の点におい
ては実施例４の場合の同様にして、黒色水性イン
キ組成物を調製した。
次に、実施例１〜４において得た本発明水性イ
ンキ組成物と比較例１〜４において得た水性イン
キ組成物との性能の比較を表１に示す。[Table] The water-based ink composition according to the present invention contains a dye represented by the general formula () in water and a water-soluble organic solvent,
It is also prepared by mixing with a water-soluble surfactant, water-soluble resin, additives, etc. as necessary. Examples of the water-soluble organic solvent to be mixed with the dye of general formula () include glycol solvents such as ethylene glycol, diethylene glycol, propylene glycol, and thiodiglycol, cellosol solvents, alcohol solvents, carbitol solvents, and alkanolamines. etc. The water-soluble surfactants to be mixed with the dye of the general formula () if necessary include N-alkylpyrrolidone, vinylpyrrolidone derivatives, anionic surfactants, nonionic surfactants, and amphoteric surfactants. agents, etc. Furthermore, if necessary, the general formula ()
Examples of the water-soluble resin to be mixed with the dye include natural or synthetic water-soluble resins, and additives such as PH regulators, preservatives, rust preventives, or metal sequestrants can also be used. . The aqueous ink compositions of the present invention with various colors obtained as described above have clear tones, excellent water resistance and light resistance, are not corrosive to metals, and can also be used as complementary colors to other colors. It has excellent performance and is ideal as ink for writing instruments, stamp ink, jet printing ink, recorder ink, etc. Examples of the present invention are described above. Note that parts by weight are abbreviated as parts. Example 1 Dye (Na salt) of dye example (1) 5 parts ethylene glycol 10 parts diethylene glycol 10 parts thiodiglycol 5 parts butyl cellosolve 0.5 parts anionic surfactant (product name: Hytenol
08) 0.2 parts Preservative 0.5 parts Distilled water 68.5 parts The above formulations were mixed and dissolved at 60 to 70°C, and then filtered through industrial filter paper to prepare a black aqueous ink composition according to the present invention. When the obtained ink composition was placed in a felt-tip pen container and a writing test was conducted, it was found that there was no ink blurring at the pen tip, the ink always flowed out smoothly, the handwriting was clear in tone, and it had excellent water resistance. and light resistance. Example 2 The invention was carried out in the same manner as in Example 1, except that 5 parts of the dye (Li salt) of Dye Example (2) was used in place of the dye used in Example 1. Such a red aqueous ink composition was obtained. The obtained ink composition had excellent performance similar to the composition of Example 1. Example 3 Dye (Na salt) of dye example (6) 8 parts ethylene glycol 10 parts diethylene glycol 10 parts propylene glycol 5 parts anionic surfactant (product type: Hitenol
08) 0.2 parts Preservative 0.5 parts Distilled water 66.3 parts The above formulation was treated in the same manner as in Example 1 to obtain a brown water-based ink composition according to the present invention. The obtained ink composition had excellent performance similar to the composition of Example 1. Example 4 The invention was carried out in the same manner as in Example 3 except that 8 parts of the dye (Na salt) of Dye Example (7) was used in place of the dye used in Example 3. Such a black aqueous ink composition was obtained. The obtained ink composition had excellent performance similar to the composition of Example 1. Comparative Example 1 A yellow aqueous ink composition was prepared in the same manner as in Example 1 except that 5 parts of tartrazine (CIAcid Yellow 23) was used in place of the dye used in Example 1. Comparative Example 2 A red aqueous ink composition was prepared in the same manner as in Example 2 except that 5 parts of CIAcid Red 18 was used in place of the dye used in Example 2. Comparative Example 3 Water Brown was used instead of the dye used in Example 3.
#16 [Manufactured by Orient Chemical Industry Co., Ltd., tartrazine,
Newcoccin, water-soluble steel phthalocyanine (CI
Using 8 parts of Direct Blue 87), the other aspects were the same as in Example 3,
A brown water-based ink composition was prepared. Comparative Example 4 A black aqueous ink composition was prepared in the same manner as in Example 4 except that 3 parts of CI Direct Black 154 was used in place of the dye used in Example 4. Next, Table 1 shows a comparison of performance between the aqueous ink compositions of the present invention obtained in Examples 1 to 4 and the aqueous ink compositions obtained in Comparative Examples 1 to 4.
【表】
実施例 ５
染料例(3)の染料（Ｋ塩） ５部
ジエチレングリコール 11部
トリエタノールアミン ２部
防腐剤 0.2部
蒸溜水 81.8部
上記配合物を30〜40℃にて混合・溶解させた
後、工業用ろ紙でろ過し、次いでポアーサイズ
0.8μのメンブランフイルターにてろ過精製して、
赤色ジエツト印刷用インキ組成物を調製した。
得られたインキ組成物は、溶液として安定性に
優れ、インキによる目詰りを起さず、ジエツト印
刷方式による印刷物は鮮明な色調を示し、耐水性
は良好であつた。
実施例 ６
染料例(9)の染料（Na塩） ５部
トリエチレングリコール 11部
Ｎ−メチル−２−ピロリドン ２部
防腐剤 0.2部
蒸溜水 81.8部
上記配合物を30〜40℃にて混合・溶解させた
後、工業用ろ紙でろ過し、次いでポアーサイズ
0.8μのメンブランフイルターにてろ過精製して、
青色ジエツト印刷用インキ組成物を調製した。
得られたインキ組成物は、溶液として安定性に
優れ、インキによる目詰りを起きず、ジエツト印
刷方式により印刷物は鮮明な色調を示し、耐水性
は良好であつた。[Table] Example 5 Dye (K salt) of dye example (3) 5 parts diethylene glycol 11 parts triethanolamine 2 parts Preservative 0.2 parts Distilled water 81.8 parts The above formulations were mixed and dissolved at 30 to 40°C. After that, it is filtered with industrial filter paper, and then the pore size is
Purify by filtration with a 0.8μ membrane filter,
A red jet printing ink composition was prepared. The obtained ink composition had excellent stability as a solution and did not cause clogging due to ink, and prints produced by jet printing showed clear color tone and had good water resistance. Example 6 Dye (Na salt) of dye example (9) 5 parts Triethylene glycol 11 parts N-methyl-2-pyrrolidone 2 parts Preservative 0.2 parts Distilled water 81.8 parts The above formulation was mixed at 30-40°C. After dissolving, filter through industrial filter paper, then check the pore size.
Purify by filtration with a 0.8μ membrane filter,
An ink composition for blue jet printing was prepared. The obtained ink composition had excellent stability as a solution, did not cause clogging due to ink, printed matter showed clear color tone by jet printing, and had good water resistance.
Claims (1)
性インキ組成物。 ［式〔〕中、 D1は、遊離酸の形において次式〔〕 （式〔〕中、 ｎは１又は２を示し、 Ｚは、 Arまたは【式】を示す。 但し、Arは、メトキシ基、スルホン基及びハ
ロゲンからなる群から選ばれた１の置換基或は同
種又は別種の２の置換基によつて置換されたベン
ゼン系のジアゾ成分残基を示し、 Ｘ及びＹは、互いに独立して水素、メチル基又
はメトキシ基を示す。） で表わされるアミノ基を有する水溶性アゾ染料残
基または水溶性アントラキノン染料残基を示し、 Ｒは、下記式乃至で表わされる基からなる
群から選ばれた活性水素を有する水溶性窒素化合
物の残基を示し、 −NHC2H4NHC3H6Si（OH）3 D2は、式〔〕で表わされるアミノ基を有す
る水溶性アゾ染料残基、水溶性アントラキノン染
料残基、または上記Ｒを示す。[Claims] 1. General formula An aqueous ink composition characterized by containing a dye represented by: [Formula [], D 1 is the following formula [] in the free acid form: (In the formula [], n represents 1 or 2, and Z represents Ar or [Formula]. However, Ar is one substituent selected from the group consisting of a methoxy group, a sulfone group, and a halogen, or Indicates a benzene-based diazo component residue substituted with two substituents of the same type or different types, and X and Y each independently represent hydrogen, a methyl group, or a methoxy group. R represents a water-soluble azo dye residue or a water-soluble anthraquinone dye residue having an active hydrogen selected from the group consisting of groups represented by the following formulas, −NHC 2 H 4 NHC 3 H 6 Si(OH) 3 D 2 represents a water-soluble azo dye residue having an amino group represented by the formula [], a water-soluble anthraquinone dye residue, or the above R.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59223567A JPS61101576A (en) | 1984-10-23 | 1984-10-23 | Water based ink composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59223567A JPS61101576A (en) | 1984-10-23 | 1984-10-23 | Water based ink composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61101576A JPS61101576A (en) | 1986-05-20 |
| JPH0552867B2 true JPH0552867B2 (en) | 1993-08-06 |
Family
ID=16800181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59223567A Granted JPS61101576A (en) | 1984-10-23 | 1984-10-23 | Water based ink composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61101576A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0468922B1 (en) * | 1990-07-24 | 1995-11-15 | Ciba-Geigy Ag | Use of polyazodyes for dyeing leather |
| CN102127308A (en) * | 2010-12-29 | 2011-07-20 | 黄山普米特新材料有限公司 | Read active dye and preparation method thereof |
-
1984
- 1984-10-23 JP JP59223567A patent/JPS61101576A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61101576A (en) | 1986-05-20 |
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