JPH0391576A - Recording liquid - Google Patents
Recording liquidInfo
- Publication number
- JPH0391576A JPH0391576A JP1227181A JP22718189A JPH0391576A JP H0391576 A JPH0391576 A JP H0391576A JP 1227181 A JP1227181 A JP 1227181A JP 22718189 A JP22718189 A JP 22718189A JP H0391576 A JPH0391576 A JP H0391576A
- Authority
- JP
- Japan
- Prior art keywords
- group
- recording liquid
- water
- recording
- solvent
- 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
Links
- 239000007788 liquid Substances 0.000 title claims description 30
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- -1 SO3M Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract description 7
- 238000001454 recorded image Methods 0.000 abstract description 4
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 abstract description 2
- 230000007774 longterm Effects 0.000 abstract description 2
- 239000004094 surface-active agent Substances 0.000 abstract description 2
- 239000012530 fluid Substances 0.000 abstract 2
- 238000013329 compounding Methods 0.000 abstract 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 abstract 1
- SSGGNFYQMRDXFH-UHFFFAOYSA-N sulfanylurea Chemical compound NC(=O)NS SSGGNFYQMRDXFH-UHFFFAOYSA-N 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はインクジェット記録用及び筆記具用の記録液と
して好適なブラックの記録液に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a black recording liquid suitable as a recording liquid for inkjet recording and writing instruments.
この種の記録液においては、用いられる溶剤は、印字に
際して、PPC用紙、ファンホールド紙の様な一般的な
オフィスにおいて汎用されている紙に対し、定着が速く
、かつ印字品位が良好であることが要求されるほか、保
存時の安定性等も必要であり、使用できる溶剤が著しく
制限されるのが現状である。In this type of recording liquid, the solvent used must have fast fixation and print quality when printing on papers commonly used in general offices, such as PPC paper and fan-hold paper. In addition to the above requirements, stability during storage is also required, and the current situation is that the solvents that can be used are severely limited.
一方、これらの記録液に用いられる染料に関しては、前
記の様な限られた溶剤に対し、十分な溶解性を有し、長
期に保存した場合でも安定であることの他、印字された
画像の濃度が高く、耐水性、耐光性、耐オゾン性に優れ
ていること等が要求されている。On the other hand, the dyes used in these recording liquids have sufficient solubility in the limited solvents mentioned above, are stable even when stored for long periods of time, and are also stable in printed images. It is required to have high concentration, excellent water resistance, light resistance, and ozone resistance.
上記の様な多くの要求を同時に満足させることは、相当
に困難である。とりわけ、耐光性及び耐オゾン性に関し
ては、他の印字方式(例えば、電子写真方式、感熱溶融
転写方式等)において、着色剤として用いられている顔
料(有機および無機)の耐光性及び耐オゾン性が優れて
いるため、顔料に対抗し得る耐光性及び耐オゾン性の良
い染料を含有するインクジェット記録用及び筆記用具用
の記録液の開発が強く要求されている。It is quite difficult to satisfy many of the above requirements at the same time. In particular, with regard to light resistance and ozone resistance, the light resistance and ozone resistance of pigments (organic and inorganic) used as colorants in other printing methods (e.g., electrophotographic methods, heat-sensitive melt transfer methods, etc.) Therefore, there is a strong demand for the development of recording liquids for inkjet recording and writing instruments containing dyes with good light fastness and ozone fastness that can compete with pigments.
このために、特開昭55−144,065号、特開昭5
7−30.773号、特開昭57−207.660号、
特開昭58−147,470号、特開昭62−190.
269号、特開昭62−190.271号、特開昭62
−190.272号、特開昭62−250.082号等
、多くの出願がなされているものの、市場の要求を完全
に満足するには至っていない。For this purpose, JP-A-55-144,065, JP-A-5
No. 7-30.773, JP-A-57-207.660,
JP-A-58-147,470, JP-A-62-190.
No. 269, JP-A-62-190.271, JP-A-62
Although many applications have been filed, such as No. 190.272 and Japanese Unexamined Patent Publication No. 62-250.082, market demands have not yet been completely satisfied.
本発明は溶解性が高く、長期間保存した場合でも安定で
あり、かつ印字された画像の濃度が高くしかも耐水性・
耐光性とりわけ耐オゾン性に優れた染料を含有するブラ
ックの記録液の提供を目的とするものである。The present invention has high solubility, is stable even when stored for a long period of time, has high density printed images, and is water resistant.
The object of the present invention is to provide a black recording liquid containing a dye that has excellent light resistance, particularly ozone resistance.
本発明は下記一般式(1)
(式中A、Bはアルキル基、アルコキシ基、アシルアミ
ノ基、So、M基もしくはハロゲン原子で置換されてい
ても良いフェニル基又はSO,M基で置換されたナフチ
ル基を表わし、Xは塩素原子又はアξ)基を表わし、M
はアルカリ金属、アンモニウム又はアミン塩類を表わし
、12. mは0又はlを表わす、)
で示される染料の少くとも1種を含有することを特徴と
する記録液に関する。The present invention relates to the following general formula (1) (wherein A and B are substituted with an alkyl group, an alkoxy group, an acylamino group, a So, M group, or a phenyl group which may be substituted with a halogen atom, or a SO, M group). represents a naphthyl group, X represents a chlorine atom or aξ) group, M
represents an alkali metal, ammonium or amine salt; 12. The present invention relates to a recording liquid characterized by containing at least one dye represented by the formula (m represents 0 or 1).
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
A又はBが置換されたフェニル基である場合の置換基の
アルキル基、アルコキシ基としては炭素数1〜4のアル
キル基、アルコキシ基が挙げられ、アシルアミノ基のア
シル基としてはアセチル基、フロヒオニル基等の炭素数
2〜5のアルキルカルボニル基又はベンゾイル基が挙げ
られ、ハロゲン原子としてはCr2.Fがあげられる。When A or B is a substituted phenyl group, examples of the substituent alkyl group and alkoxy group include an alkyl group having 1 to 4 carbon atoms and an alkoxy group, and examples of the acyl group of the acylamino group include an acetyl group and a fluorhionyl group. Examples of the halogen atom include an alkylcarbonyl group having 2 to 5 carbon atoms such as Cr2. I can give F.
Mで表わされるアルカリ金属としてはNa、K。The alkali metals represented by M include Na and K.
Liが挙げられ、アミン塩類としては(モノ、ジ。Examples of amine salts include Li (mono, di,
トリ←アルキルアミン、(モノ、ジ、トリ←アルカノー
ルア【ン、アルキル基及びアルカノールの両方でジー又
はトリー置換されたア【ン等が挙げられる。Examples include tri←alkylamine, (mono-, di-, tri←alkanolamine), di- or tri-substituted amine with both an alkyl group and an alkanol, and the like.
本発明に使用する一般式(1)の染料の具体例としては
以下の様のものが挙げられる。Specific examples of the dye of general formula (1) used in the present invention include the following.
磁2
血4
M : IbN(C!HnOH)z
磁5
Na6
Na7
S〇−軸
本発明の化合物は、例えば細田豊著「新染料化学」 (
昭和48年12月21日発行、技報堂)第396頁第1
行ないし第407真上から14行及び第441真下から
4行〜第442買上から5行の記載に順じて通常のジア
ゾ化、カップリング及びトリアジニル化することにより
製造することができる。Magnetic 2 Blood 4 M: IbN(C!HnOH)z Magnetic 5 Na6 Na7 S〇-axis The compound of the present invention can be found, for example, in "New Dye Chemistry" by Yutaka Hosoda (
Published December 21, 1972, Gihodo) No. 396, No. 1
It can be produced by conventional diazotization, coupling and triazinylation according to the descriptions in line 14 from the top of line 407 and line 4 from line 441 to line 5 from line 442.
上記染料の含有量としては、記録液全重量に対して0.
5〜8%の範囲、好ましくは2〜5%の範囲が挙げられ
る。The content of the above-mentioned dye is 0.0% based on the total weight of the recording liquid.
A range of 5 to 8%, preferably a range of 2 to 5% is mentioned.
本発明の記録液に用いられる溶剤としては、水の他、水
溶性有機溶剤としてエチレングリコール、プロピレング
リコール、ブチレンゲリコール、ジエチレングリコール
、トリエチレングリコール、ポリエチレングリコール(
#200)、ポリエチレングリコール(#400)、グ
リセリン、N−メチル−ピロリドン、N−エチル−ピロ
リドン、N−ビニル−ピロリドン、1.3−ジメチル−
イミダシリジノン、エチレングリコールモノアリルエー
テル、エチレングリコールモノメチルエーテル、ジエチ
レングリコールモノメチルエーテル等を含有しているの
が好ましく、水及び水溶性有機溶剤の含有量としては、
それぞれ記録液全重量に対し、10〜90重量%、好ま
しくは10〜70重量%、より好ましくは10〜50重
量%の範囲が挙げられる。In addition to water, examples of solvents used in the recording liquid of the present invention include water-soluble organic solvents such as ethylene glycol, propylene glycol, butylene gelicol, diethylene glycol, triethylene glycol, and polyethylene glycol (
#200), polyethylene glycol (#400), glycerin, N-methyl-pyrrolidone, N-ethyl-pyrrolidone, N-vinyl-pyrrolidone, 1,3-dimethyl-
It is preferable to contain imidasilidinone, ethylene glycol monoallyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, etc., and the content of water and water-soluble organic solvent is as follows:
The amount of each of these is 10 to 90% by weight, preferably 10 to 70% by weight, and more preferably 10 to 50% by weight, based on the total weight of the recording liquid.
また、本発明の記録液のpHは6〜8が望ましい。Further, the pH of the recording liquid of the present invention is preferably 6 to 8.
さらに本発明の記録液は記録液全重量に対し0゜1−1
0重量%、好ましくは0.5〜5重量%の尿素、チオ尿
素、ビウレット、セ逅カルバジドから選ばれる化合物を
添加したり、又0.001〜0.5重量%の界面活性剤
を添加することにより印字後の速乾性及び印字品位をよ
り一層改良することができる。Furthermore, the recording liquid of the present invention has a temperature of 0°1-1 based on the total weight of the recording liquid.
0% by weight, preferably 0.5 to 5% by weight of a compound selected from urea, thiourea, biuret, and carbazide, or 0.001 to 0.5% by weight of a surfactant. This makes it possible to further improve the quick-drying properties and print quality after printing.
本発明の記録液は、インクジェット記録用、筆記用具用
等のブラックの記録液として用いられ、普通紙に記録し
た場合でも、記録画像の耐光性、耐水性及び耐オゾン性
に優れている他、記録液としての保存安定性も良好であ
る。The recording liquid of the present invention is used as a black recording liquid for inkjet recording, writing instruments, etc., and even when recorded on plain paper, the recorded image has excellent light resistance, water resistance, and ozone resistance. The storage stability as a recording liquid is also good.
本発明を以下の実施例で更に詳細に説明するが、本発明
はこれら実施例により何等限定されるものではない。The present invention will be explained in more detail with reference to the following examples, but the present invention is not limited to these examples in any way.
実施例1
エチレングリコールモノアリルエーテル 25エチレン
グリコール 22前記11kklの
化合物 3.5合 計
100上記の各成分を容器
の中で充分混合溶解し、孔径1μのテフロンフィルター
で加圧濾過したのち、真空ポンプ及び超音波を用いて脱
気処理し記録液を調製した。Example 1 Ethylene glycol monoallyl ether 25 ethylene glycol 22 11 kkl of the above compound 3.5 total
100 The above components were thoroughly mixed and dissolved in a container, filtered under pressure through a Teflon filter with a pore size of 1 μm, and then degassed using a vacuum pump and ultrasonic waves to prepare a recording liquid.
得られた記録液を用いて、インクジェットプリンター(
HG−4800、エプソン株式会社製造)でインクジェ
ット記録を行ない、下記(a)及び(ロ)の方法に従っ
て、インクジェット記録に関する評価を行った。Using the obtained recording liquid, inkjet printer (
Inkjet recording was performed using HG-4800 (manufactured by Epson Corporation), and the inkjet recording was evaluated according to the methods (a) and (b) below.
(a) 記録液の長期保存性:記録液をガラス容器に
密閉し、10″Cと60″Cで6ケ月間保存したのちで
も不溶分の析出は認められず、液の物性・や色調にも変
化がなかった。(a) Long-term storage stability of recording liquid: Even after recording liquid was sealed in a glass container and stored at 10"C and 60"C for 6 months, no precipitation of insoluble matter was observed, and the physical properties and color tone of the liquid did not change. There was no change.
(ロ)記録画像の品質:記録された画像はブランク色で
濃度が高く鮮明であった。室内光に3力月さらしたのち
の濃度の低下率は1%以下であり、また、キセノンフェ
ードメーター(スガ試験機■製造)により100時間露
光後の濃度の低下率は7%と低かった。(b) Quality of recorded image: The recorded image was blank in color, had high density, and was clear. The rate of decrease in density after three months of exposure to room light was less than 1%, and the rate of decrease in density after 100 hours of exposure using a xenon fade meter (manufactured by Suga Shikenki ■) was as low as 7%.
又、オゾン12ppmを含有する空気中に90分間曝露
した際の変退色(ΔE′″)の値を前後の色差としてJ
IS Z8730により求めたところ、その値は4と
小さいものであった。In addition, J
When determined using IS Z8730, the value was as small as 4.
又、水中に24時間浸漬した後の画像のにじみはわずか
であり又濃度の低下も小さかった。Further, after 24 hours of immersion in water, there was only slight blurring of the image and a small decrease in density.
実施例2
記録液の組成 使用量(重量%)
グリセリン 10エチレングリ
コール 10前記Nα3の化合物
使用量
(重量%)
合 計 100実施例
1と同様にして上記組成の記録液を調製し、(a)及び
(ロ)の検討を行った結果、いずれも良好な結果を得た
。Example 2 Composition of recording liquid Amount used (wt%) Glycerin 10 Ethylene glycol 10 Amount of the above Nα3 compound used (wt%) Total 100 A recording liquid with the above composition was prepared in the same manner as in Example 1, and (a) As a result of examining (2) and (b), favorable results were obtained in both cases.
実施例3
記録液の!Il威
ジエチレングリコールモノブチルエーテル 5グリセリ
ン 15前記弘2の化合物
2合 計
100実施例1の方法に従って、上記のa
威から成る記録液を調製し、実施例1に記載の(a)及
び(ハ)の方法に従って、評価を行なった結果、いずれ
も良好であった。Example 3 Recording liquid! Diethylene glycol monobutyl ether 5 Glycerin 15 Compound of Ko 2 above
2 total
100 According to the method of Example 1, above a
A recording liquid consisting of the following liquid was prepared and evaluated according to the methods (a) and (c) described in Example 1. As a result, all of the recording liquids were good.
実施例4〜7
実施例1におけるぬ1の化合物の代りにNα4゜Na5
.Nap、Na7の化合物を各々用いて記録液を調製し
、
実施例1と同様にして評価を行った結果、いずれも良好
であった。Examples 4 to 7 Nα4゜Na5 in place of the compound No. 1 in Example 1
.. Recording liquids were prepared using the Nap and Na7 compounds and evaluated in the same manner as in Example 1. As a result, both were good.
Claims (1)
ノ基、SO_3M基もしくはハロゲン原子で置換されて
いても良いフェニル基又はSO_3M基で置換されたナ
フチル基を表わし、Xは塩素原子又はアミノ基を表わし
、Mはアルカリ金属、アンモニウム又はアミン塩類を表
わし、l、mは0又は1を表わす。) で示される染料の少くとも1種を含有することを特徴と
する記録液。[Claims] Solvent and the following general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] (In the formula, A and B are an alkyl group, an alkoxy group, an acylamino group, an SO_3M group, or a halogen Represents a phenyl group which may be substituted with an atom or a naphthyl group substituted with an SO_3M group, X represents a chlorine atom or an amino group, M represents an alkali metal, ammonium or amine salt, l, m are 0 or 1.) A recording liquid characterized by containing at least one dye represented by:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1227181A JPH0391576A (en) | 1989-09-01 | 1989-09-01 | Recording liquid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1227181A JPH0391576A (en) | 1989-09-01 | 1989-09-01 | Recording liquid |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0391576A true JPH0391576A (en) | 1991-04-17 |
Family
ID=16856759
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1227181A Pending JPH0391576A (en) | 1989-09-01 | 1989-09-01 | Recording liquid |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0391576A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0626428A1 (en) | 1993-05-18 | 1994-11-30 | Canon Kabushiki Kaisha | Azo dye compounds, ink containing the same, and recording method and instrument using the ink |
US5820661A (en) * | 1996-04-25 | 1998-10-13 | Zeneca Limited | Ink compositions containing disazo dyes |
US6858069B2 (en) | 2001-10-26 | 2005-02-22 | Seiko Epson Corporation | Black aqueous ink composition, ink jet recording process using the same, and recorded matter |
DE10218503B4 (en) * | 2001-04-26 | 2006-01-26 | Mitsubishi Paper Mills Limited | Ink jet recording material and ink for ink jet recording |
US7094279B2 (en) | 2003-11-25 | 2006-08-22 | Seiko Epson Corporation | Black water-based ink composition |
-
1989
- 1989-09-01 JP JP1227181A patent/JPH0391576A/en active Pending
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0626428A1 (en) | 1993-05-18 | 1994-11-30 | Canon Kabushiki Kaisha | Azo dye compounds, ink containing the same, and recording method and instrument using the ink |
US5466282A (en) * | 1993-05-18 | 1995-11-14 | Canon Kabushiki Kaisha | Azo dye compound, ink containing the same, and recording method and instrument using the ink |
US5820661A (en) * | 1996-04-25 | 1998-10-13 | Zeneca Limited | Ink compositions containing disazo dyes |
DE10218503B4 (en) * | 2001-04-26 | 2006-01-26 | Mitsubishi Paper Mills Limited | Ink jet recording material and ink for ink jet recording |
US6858069B2 (en) | 2001-10-26 | 2005-02-22 | Seiko Epson Corporation | Black aqueous ink composition, ink jet recording process using the same, and recorded matter |
US7094279B2 (en) | 2003-11-25 | 2006-08-22 | Seiko Epson Corporation | Black water-based ink composition |
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