JPS5974173A - Red water-base ink - Google Patents

Red water-base ink

Info

Publication number
JPS5974173A
JPS5974173A JP18463782A JP18463782A JPS5974173A JP S5974173 A JPS5974173 A JP S5974173A JP 18463782 A JP18463782 A JP 18463782A JP 18463782 A JP18463782 A JP 18463782A JP S5974173 A JPS5974173 A JP S5974173A
Authority
JP
Japan
Prior art keywords
water
formula
base ink
solvents
red
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.)
Pending
Application number
JP18463782A
Other languages
Japanese (ja)
Inventor
Satoshi Mori
聡 毛利
Toshihiko Matsuura
松浦 敏彦
Nobuyuki Yamanaka
山中 信行
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Kayaku Co Ltd
Original Assignee
Nippon Kayaku Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd
Priority to JP18463782A priority Critical patent/JPS5974173A/en
Publication of JPS5974173A publication Critical patent/JPS5974173A/en
Pending legal-status Critical Current

Links

Landscapes

  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

PURPOSE:To provide a red water-base ink having good resistance to light and water, by incorporating a particular dye. CONSTITUTION:A water-base ink which contains a dye of formula I (wherein R1 is H, 1-8C alkyl; R2, R3, R4 are H, methyl; X is H, methyl; n is 1-3; M is H, an alkali metal). colorants particularly C.I. Acid Red 143 of formula II and C.I. Acid Red 143:1 of formula III among dyes of formula I do not cause crystallization, gelation, coalescence, etc., and they are excellent in shelf stability when used in a water-base ink which comprises colorants, water, and solvents at the least. Solvents compatible with water and capable of liquefying colorants well, and having moderate hygroscopicity capable of controlling evaporation of moisture properly are preferable as solvents for inks and include solvents such as glycols, cellosolves, and carbitols.

Description

【発明の詳細な説明】[Detailed description of the invention]

本発明は耐光堅牢なる赤色水性インクに関するものであ
る。 従来水性インクは筆記用、スタンフ゛用、ンエノトイン
ク用、記録用等75(ある力S、着色前1](隊υ料)
としては直接染料、酸性染ネヰ、」嘉基灼二染木−1が
使用されている。 直接性染料よりなる水(’Iインク(工、 iiiに面
I水性は良好であるが、鮮H月さに欠U゛、!I存に赤
色においてその傾向が太きい。又1甚基+’1g梶g享
・Yしま食洋明であるが耐水性にかけ、而・1光+’4
E +1著しく劣る。 酸性染料はちょうど両者のrlI」間の性質を有するが
鮮明にして而」光及び耐水力;堅刻二なる着色前11し
工見当らない。壕だ、インク類のうちインク・ジェット
方式用のカラーインクG′!、、言己釘、、伺
The present invention relates to a red water-based ink that is light-fast. Conventional water-based inks are for writing, stamping, notebook ink, recording, etc. 75 (a certain force S, 1 before coloring) (team material)
Direct dyes, acid dyes, and ``Kakiroji Someki-1'' are used. Water ('I ink) made of direct dyes has good water resistance, but lacks freshness, and this tendency is more pronounced in red. '1g Kaji g Kyou, Y Shima Shoku Yomei, but it is water resistant, and 1 light + '4
E +1 significantly inferior. Acidic dyes have properties that are just between the two, but they are bright, light and water resistant; they are hard to find before coloring. Of all the inks, color ink G' for inkjet methods! ,,Konkikugi,,Kiki

【のp丁
現=1g+:、保存性が重視されるととカ・ら色A目の
IIn明さのイ山耐水、耐光性が優れ、結晶析1」Aや
ケルイヒカー起らない着色剤か望まれている。 本発明者はこのような問題の1++イ決を目1′白とし
インク用赤色着色剤の探索を11つjこところ、−(釦
式(I)の着色剤は上記裂刃〈さ1.ltろ・1化坐1
を有1〜ろことを見い出した。 (式中、1(・2.1%3. R4はそれぞれ水素原子
又はメチル基、R,は水素原子又は炭素数1〜8のアル
キル基を、Xは水素原子又はメチル基を示す。 11は1〜3の整数を、Mは水素原子又はアルカリ金属
を示す。) 一般式(I)で表わされろものの中では、特にCI  
Ac1d T(、ed  1 4 3及び CT、  Ac1cl Red  1 43  :  
1で示される着色剤はいずれも制光性、祠水件がすぐれ
、又水性インクとした場合、結晶析出、ゲル化、会合な
どが起らず保存性がすぐれている。 本発明の水性インクは着色剤、水及び溶剤とから少なく
ともなるが、インクに用いる溶剤としては水と相溶して
前述の着色剤をよく溶解する性質を持ち、かつ適度の吸
湿性を有し水分の蒸発を適度に制御出来る浴剤が好甘し
く、例えハ、エチレングリコール、ジエチレングリコー
ル、チオジグリコール等のグリコール系溶剤、セルソル
ブ系溶剤あるいはツノルビトール系溶剤等がある。本発
明の水性インク中における%f色剤の含有率は2〜30
重量%、溶剤は5〜50重量%、水は40〜90重量%
の比率が好址しい。さらに溶解性、溶解安定性をよくす
る目的でアニオン系又はノニオン系活4牛剤′75り用
いら諸tでもよい。これらは水性インクに対し0.2〜
2重扇%用いるのが好寸しい。 以下実施例により本発明を説明する。この中で「部」と
は重量部を意味する。 実施例1 後記式(IV)の化合物を次のように合成した。 】−アミノ−2−(4’−オクチルフェノキシ)−4−
(2’、 6’−ジメチルアニリノ)アントラキノ75
5部、ベンツ酢酸エチルエステル 200部の0−ジクロルベンゼンに溶解懸濁し、60C
で4時間加熱反応した。固形分をP31J分離後乾燥し
、乾燥固形分67部を得た。本化合物Qま元 原素分析値、N M R,により式(TV)の化学構造
を有することか、判明した0 本化合物全量を500部、5%発煙硫酸中200でスル
ホン化した。氷水にあけ固形分を′/P男11分禽■し
、苛性ソーダで中和乾燥し107音μの卓乞燥固水分を
得た。本化合物は弐■の化学(構造を有する。 実施例2。 実施例1で得られた弐Mの染料    15部ジエチル
グリコール         20部プロピレングリコ
ール        10部ノイゲンP(第−工業製薬
鋼→製    。2了、1、ノニオン界面活性剤) 水                   543部を
混合し、次いで攪拌溶解し、後工業用E紙でP、 過し
不溶群発を除去し赤色インキを得た。 上記インキは鮮明な帯青色を呈し、)制光性、耐水性に
寸ぐJ′シ特にインクジェット用インクとして化チ 身
′し て い /こ 。 実施例:3〜7 下記の構造の染料を用いて実施例2と同様な方法で・イ
ンクを製造した。これらは筆記用、スタンプ井1、ジェ
ットインク用に使用すると優れた性質を示した。 実施例6゜ 式(印の化合物          赤実施例7 式(1)の化合物          赤特許出願人 
日本化薬株式会社 523
[P = 1g +: When preservation is important, it is a color that has excellent water resistance and light resistance, and does not cause crystallization 1"A or kerosene. desired. The inventors of the present invention set out to solve this problem by searching for a red colorant for ink. ltro・1kaza 1
I found that there are 1 to 100 words. (In the formula, 1(・2.1%3. R4 is a hydrogen atom or a methyl group, R is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and X is a hydrogen atom or a methyl group. 11 is (M represents a hydrogen atom or an alkali metal.) Among those represented by the general formula (I), especially CI
Ac1d T(, ed 1 4 3 and CT, Ac1cl Red 1 43:
All of the colorants shown in No. 1 have excellent light control properties and water repellency, and when used as water-based inks, they do not cause crystal precipitation, gelation, association, etc., and have excellent preservability. The water-based ink of the present invention consists of at least a colorant, water, and a solvent, and the solvent used in the ink has a property of being compatible with water and dissolving the colorant well, and has a suitable hygroscopicity. Bath agents that can appropriately control water evaporation are preferred, such as glycol solvents such as ethylene glycol, diethylene glycol, and thiodiglycol, cellosolve solvents, and tunorbitol solvents. The content of %f colorant in the aqueous ink of the present invention is 2 to 30
% by weight, solvent 5-50% by weight, water 40-90% by weight
The ratio remains favorable. Furthermore, for the purpose of improving solubility and dissolution stability, anionic or nonionic active agents may be used. These are 0.2~ for water-based ink.
It is best to use double fans. The present invention will be explained below with reference to Examples. Herein, "parts" means parts by weight. Example 1 A compound of formula (IV) described below was synthesized as follows. ]-Amino-2-(4'-octylphenoxy)-4-
(2', 6'-dimethylanilino) anthraquino 75
5 parts of benzacetic acid ethyl ester was dissolved and suspended in 200 parts of 0-dichlorobenzene and heated at 60C.
The mixture was heated and reacted for 4 hours. The solid content was separated from P31J and dried to obtain 67 parts of dry solid content. The present compound Q was found to have the chemical structure of formula (TV) by elemental analysis and NMR.500 parts of the total amount of the present compound was sulfonated with 200 parts in 5% oleum. The solid content was poured into ice water and boiled for 11 minutes, neutralized and dried with caustic soda to obtain a dry solid moisture of 107 μm. This compound has the chemical structure of 2. Example 2. 2M dye obtained in Example 1 15 parts diethyl glycol 20 parts propylene glycol 10 parts Neugen P (manufactured by Dai-Kogyo Seiyaku Steel → Co., Ltd.) , 1, nonionic surfactant) was mixed with 543 parts of water, then stirred and dissolved, and then washed with industrial grade E paper to remove insoluble clusters to obtain a red ink.The above ink exhibited a clear blueish color. ,) It has been transformed into an inkjet ink with excellent light control and water resistance properties. Examples: 3 to 7 Inks were produced in the same manner as in Example 2 using dyes with the following structures. These exhibited excellent properties when used for writing, stamping, and jet ink. Example 6 Compound of formula (marked red) Example 7 Compound of formula (1) Red patent applicant
Nippon Kayaku Co., Ltd. 523

Claims (1)

【特許請求の範囲】[Claims] (1)下記一般式で示される染料を含有する赤色水性イ
ンク (式中、T’1.、、 、1.3. Tj4はそれぞれ
水素原子又はメチル基を、R1は水素原子又は炭素数1
〜8のアルキル基を、Xは水素原子又はメチル基を、I
]は1〜,3の整数を、Mは水素原子又はアルカリ金属
を示す。)
(1) A red water-based ink containing a dye represented by the following general formula (wherein T'1., , 1.3. Tj4 is a hydrogen atom or a methyl group, R1 is a hydrogen atom or a carbon number 1)
-8 alkyl group, X is a hydrogen atom or a methyl group, I
] represents an integer of 1 to 3, and M represents a hydrogen atom or an alkali metal. )
JP18463782A 1982-10-22 1982-10-22 Red water-base ink Pending JPS5974173A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP18463782A JPS5974173A (en) 1982-10-22 1982-10-22 Red water-base ink

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP18463782A JPS5974173A (en) 1982-10-22 1982-10-22 Red water-base ink

Publications (1)

Publication Number Publication Date
JPS5974173A true JPS5974173A (en) 1984-04-26

Family

ID=16156712

Family Applications (1)

Application Number Title Priority Date Filing Date
JP18463782A Pending JPS5974173A (en) 1982-10-22 1982-10-22 Red water-base ink

Country Status (1)

Country Link
JP (1) JPS5974173A (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998011167A1 (en) * 1996-09-11 1998-03-19 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compounds, water-base ink composition, and articles colored therewith
EP1063268A1 (en) * 1998-03-10 2000-12-27 Nippon Kayaku Kabushiki Kaisha Water-based magenta ink composition and method of ink-jet recording
WO2001018123A1 (en) * 1999-09-03 2001-03-15 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compound, aqueous magenta ink compositions and ink-jet recording method
EP1123932A1 (en) * 1998-10-22 2001-08-16 Nippon Kayaku Kabushiki Kaisha Novel anthrapyridone compounds, water-based magenta ink composition, and method of ink-jet printing
EP1164174A1 (en) 2000-06-12 2001-12-19 Canon Kabushiki Kaisha Ink set, ink jet recording apparatus, ink jet recording method, recording unit, and ink cartridge
US7015327B2 (en) 2001-09-26 2006-03-21 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compounds, water-base magenta ink compositions and method of ink-jet recording
US7025816B2 (en) * 2003-11-19 2006-04-11 Konica Minolta Holdings, Inc. Anthraquinone dye and inkjet recording liquid
US7520926B2 (en) 2006-09-15 2009-04-21 Videojet Technologies Inc. Solvent-based ink composition
US7727320B2 (en) 2005-01-17 2010-06-01 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compound, magenta ink composition and colored matter
US7740694B2 (en) 2006-06-30 2010-06-22 Videojet Technologies Inc Ink jet ink composition and method for printing
US7785410B2 (en) 2006-06-30 2010-08-31 Videojet Technologies Inc. Ink jet ink composition and method for printing on substrates under conditions of high static electrical charge
US7947124B2 (en) 2006-06-30 2011-05-24 Videojet Technologies Inc. High electrical resistivity ink jet ink composition
WO2013168806A1 (en) * 2012-05-11 2013-11-14 日本化薬株式会社 Ink set for inkjet printing, and method for printing fiber using same

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56155262A (en) * 1980-05-06 1981-12-01 Canon Inc Recording liquid

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56155262A (en) * 1980-05-06 1981-12-01 Canon Inc Recording liquid

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6152969A (en) * 1996-09-11 2000-11-28 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compounds, water-based ink composition, and articles colored therewith
WO1998011167A1 (en) * 1996-09-11 1998-03-19 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compounds, water-base ink composition, and articles colored therewith
EP1063268A1 (en) * 1998-03-10 2000-12-27 Nippon Kayaku Kabushiki Kaisha Water-based magenta ink composition and method of ink-jet recording
EP1063268A4 (en) * 1998-03-10 2002-07-31 Nippon Kayaku Kk Water-based magenta ink composition and method of ink-jet recording
US6530985B1 (en) 1998-03-10 2003-03-11 Nippon Kayaku Kabushiki Kaisha Water-based magenta ink composition and method of ink-jet recording
EP1123932A1 (en) * 1998-10-22 2001-08-16 Nippon Kayaku Kabushiki Kaisha Novel anthrapyridone compounds, water-based magenta ink composition, and method of ink-jet printing
EP1123932A4 (en) * 1998-10-22 2002-01-23 Nippon Kayaku Kk Novel anthrapyridone compounds, water-based magenta ink composition, and method of ink-jet printing
US6645283B1 (en) 1998-10-22 2003-11-11 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compounds, water-based magenta ink composition, and method of ink-jet printing
US6648952B1 (en) 1999-09-03 2003-11-18 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compound, aqueous magenta ink compositions and ink-jet recording method
WO2001018123A1 (en) * 1999-09-03 2001-03-15 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compound, aqueous magenta ink compositions and ink-jet recording method
EP1164174A1 (en) 2000-06-12 2001-12-19 Canon Kabushiki Kaisha Ink set, ink jet recording apparatus, ink jet recording method, recording unit, and ink cartridge
US6706100B2 (en) 2000-06-12 2004-03-16 Canon Kabushiki Kaisha Ink set, ink jet recording apparatus, ink jet recording method, recording unit, and ink cartridge
US7195664B2 (en) 2000-06-12 2007-03-27 Canon Kabushiki Kaisha Ink set, ink jet recording apparatus, ink jet recording method, recording unit, and ink cartridge
US7015327B2 (en) 2001-09-26 2006-03-21 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compounds, water-base magenta ink compositions and method of ink-jet recording
US7025816B2 (en) * 2003-11-19 2006-04-11 Konica Minolta Holdings, Inc. Anthraquinone dye and inkjet recording liquid
US7727320B2 (en) 2005-01-17 2010-06-01 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compound, magenta ink composition and colored matter
US7740694B2 (en) 2006-06-30 2010-06-22 Videojet Technologies Inc Ink jet ink composition and method for printing
US7785410B2 (en) 2006-06-30 2010-08-31 Videojet Technologies Inc. Ink jet ink composition and method for printing on substrates under conditions of high static electrical charge
US7947124B2 (en) 2006-06-30 2011-05-24 Videojet Technologies Inc. High electrical resistivity ink jet ink composition
US7520926B2 (en) 2006-09-15 2009-04-21 Videojet Technologies Inc. Solvent-based ink composition
WO2013168806A1 (en) * 2012-05-11 2013-11-14 日本化薬株式会社 Ink set for inkjet printing, and method for printing fiber using same
JPWO2013168806A1 (en) * 2012-05-11 2016-01-07 日本化薬株式会社 Ink set for ink jet printing and textile printing method using the same

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