JP2009030023A5 - - Google Patents

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JP2009030023A5
JP2009030023A5 JP2008142279A JP2008142279A JP2009030023A5 JP 2009030023 A5 JP2009030023 A5 JP 2009030023A5 JP 2008142279 A JP2008142279 A JP 2008142279A JP 2008142279 A JP2008142279 A JP 2008142279A JP 2009030023 A5 JP2009030023 A5 JP 2009030023A5
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ink
carbon atoms
sulfonic acid
carboxyl
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JP2009030023A (en
JP4632459B2 (en
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Priority to US12/136,393 priority patent/US7550037B2/en
Priority to EP08158847A priority patent/EP2011841B1/en
Priority to CN2008101080633A priority patent/CN101338094B/en
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Claims (10)

少なくとも、第1の色材、第2の色材、及び第3の色材を含有してなるインクであって、
前記第1の色材が、下記一般式(I)で表される化合物であり、
前記第2の色材が、下記一般式(II)で表される化合物であり、
前記第3の色材が、下記一般式(III)で表される化合物であることを特徴とするインク。
Figure 2009030023
(一般式(I)中、Aは置換されていてもよい芳香族基又は複素環基であり、Bは下記一般式(1)乃至(5)で表されるいずれかの基であり、Mはそれぞれ独立に、水素原子、アルカリ金属、アンモニウム、又は有機アンモニウムである。)
Figure 2009030023
(一般式(1)乃至(5)中、R1乃至R9はそれぞれ独立に、水素原子、ハロゲン原子、脂肪族基、芳香族基、複素環基、カルボキシル基、カルバモイル基、アルコキシカルボニル基、アリールオキシカルボニル基、複素環オキシカルボニル基、アシル基、ヒドロキシル基、アルコキシ基、アリールオキシ基、複素環オキシ基、シリルオキシ基、アシルオキシ基、カルバモイルオキシ基、アルコキシカルボニルオキシ基、アリールオキシカルボニルオキシ基、アニリノ基及び複素環アミノ基を含むアミノ基、アシルアミノ基、ウレイド基、スルファモイルアミノ基、アルコキシカルボニルアミノ基、アリールオキシカルボニルアミノ基、アルキル若しくはアリールスルホニルアミノ基、複素環スルホニルアミノ基、シアノ基、ニトロ基、アルキル若しくはアリールチオ基、複素環チオ基、アルキル若しくはアリールスルホニル基、複素環スルホニル基、アルキル若しくはアリールスルフィニル基、複素環スルフィニル基、スルファモイル基、又はスルホン酸基であり、各基はさらに置換されていてもよい。)
Figure 2009030023
(一般式(II)中、R10はそれぞれ独立に、水素原子、ヒドロキシル基、カルボキシル基、ヒドロキシル基若しくは炭素数1乃至4のアルコキシ基によって置換されていてもよい炭素数1乃至4のアルキル基、ヒドロキシル基若しくは炭素数1乃至4のアルコキシ基によって置換されていてもよい炭素数1乃至4のアルコキシル基、ヒドロキシル基若しくは炭素数1乃至4のアルコキシ基によって置換されていてもよい炭素数1乃至4のアルキルアミノ基、カルボキシル−炭素数1乃至5のアルキルアミノ基、ビス−〔カルボキシ−炭素数1乃至5のアルキル〕アミノ基、ヒドロキシル基若しくは炭素数1乃至4のアルコキシ基によって置換されていてもよい炭素数1乃至4のアルカノイルアミノ基、カルボキシル基若しくはスルホン酸基若しくはアミノ基で置換されていてもよいフェニルアミノ基、スルホン酸基、ハロゲン原子、又はウレイド基であり、[C]はカルボキシル基又はスルホン酸基を有する脂肪族アミン残基であり、Mはそれぞれ独立に、水素原子、アルカリ金属、アンモニウム、又は有機アンモニウムである。)
Figure 2009030023
(一般式(III)中、Dは、置換基を有するフェニル基であり、該置換基は、カルボキシル基、スルホン酸基、塩素原子、シアノ基、ニトロ基、スルファモイル基、炭素数1乃至4のアルキル基、炭素数1乃至4のアルコキシ基(ヒドロキシル基、炭素数1乃至4のアルコキシ基、スルホン酸基、又はカルボキシル基で置換されていてもよい)、及び炭素数1乃至4のアルキルスルホニル基(ヒドロキシル基、スルホン酸基、又はカルボキシル基で置換されていてもよい)からなる群から選ばれる。E及びFはそれぞれ独立に、置換基を有するパラフェニレン基であり、該置換基は、カルボキシル基、スルホン酸基、炭素数1乃至4のアルキル基、炭素数1乃至4のアルコキシ基(ヒドロキシル基、炭素数1乃至4のアルコキシ基、スルホン酸基、又はカルボキシル基で置換されていてもよい)、及び炭素数1乃至4のアルキルスルホニル基(ヒドロキシル基、スルホン酸基、又はカルボキシル基で置換されていてもよい)からなる群から選ばれる。R11は、カルボキシル基で置換されていてもよい炭素数1乃至4のアルキル基、スルホン酸基で置換されていてもよいフェニル基、又はカルボキシル基のいずれかであり、R12は、シアノ基、カルバモイル基、又はカルボキシル基のいずれかであり、R13及びR14はそれぞれ独立に、水素原子、メチル基、塩素原子、又はスルホン酸基のいずれかである。)
An ink containing at least a first color material, a second color material, and a third color material,
The first colorant is a compound represented by the following general formula (I):
The second colorant is a compound represented by the following general formula (II):
The ink, wherein the third color material is a compound represented by the following general formula (III).
Figure 2009030023
(In general formula (I), A is an optionally substituted aromatic group or heterocyclic group, B is any group represented by the following general formulas (1) to (5), M Are each independently a hydrogen atom, an alkali metal, ammonium, or organic ammonium.)
Figure 2009030023
(In the general formulas (1) to (5), R 1 to R 9 are each independently a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a carboxyl group, a carbamoyl group, an alkoxycarbonyl group, Aryloxycarbonyl group, heterocyclic oxycarbonyl group, acyl group, hydroxyl group, alkoxy group, aryloxy group, heterocyclic oxy group, silyloxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, Amino group including anilino group and heterocyclic amino group, acylamino group, ureido group, sulfamoylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, alkyl or arylsulfonylamino group, heterocyclic sulfonylamino group, cyano group , Nitro group, al A kill or arylthio group, a heterocyclic thio group, an alkyl or arylsulfonyl group, a heterocyclic sulfonyl group, an alkyl or arylsulfinyl group, a heterocyclic sulfinyl group, a sulfamoyl group, or a sulfonic acid group, each group being further substituted May be good.)
Figure 2009030023
(In the general formula (II), each R 10 independently represents a hydrogen atom, a hydroxyl group, a carboxyl group, a hydroxyl group or an alkyl group having 1 to 4 carbon atoms which may be substituted by an alkoxy group having 1 to 4 carbon atoms. 1 to 4 carbon atoms which may be substituted by a hydroxyl group or an alkoxy group having 1 to 4 carbon atoms, 1 to 4 carbon atoms which may be substituted by a hydroxyl group or an alkoxy group having 1 to 4 carbon atoms Substituted by 4 alkylamino groups, carboxyl-alkylamino groups having 1 to 5 carbon atoms, bis- [carboxy-alkyl having 1 to 5 carbon atoms] amino groups, hydroxyl groups or alkoxy groups having 1 to 4 carbon atoms. C1-C4 alkanoylamino group, carboxyl group or sulfonic acid group Or a phenylamino group optionally substituted with an amino group, a sulfonic acid group, a halogen atom, or a ureido group, [C] is an aliphatic amine residue having a carboxyl group or a sulfonic acid group, and M is Each independently a hydrogen atom, an alkali metal, ammonium, or organic ammonium.)
Figure 2009030023
(In the general formula (III), D is a phenyl group having a substituent, and the substituent is a carboxyl group, a sulfonic acid group, a chlorine atom, a cyano group, a nitro group, a sulfamoyl group, or a group having 1 to 4 carbon atoms. An alkyl group, an alkoxy group having 1 to 4 carbon atoms (which may be substituted with a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, a sulfonic acid group, or a carboxyl group), and an alkylsulfonyl group having 1 to 4 carbon atoms; Selected from the group consisting of (which may be substituted with a hydroxyl group, a sulfonic acid group, or a carboxyl group) E and F are each independently a paraphenylene group having a substituent, and the substituent is a carboxyl group Group, sulfonic acid group, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms (hydroxyl group, alkoxy group having 1 to 4 carbon atoms, sulfonic acid , Or carboxyl which may be substituted with a group), and an alkylsulfonyl group (hydroxyl group of 1 to 4 carbon atoms, selected from the group consisting of a sulfonic acid group, or may be substituted by carboxyl group) .R 11 is any of an alkyl group having 1 to 4 carbon atoms which may be substituted with a carboxyl group, a phenyl group which may be substituted with a sulfonic acid group, or a carboxyl group, and R 12 is a cyano group, It is either a carbamoyl group or a carboxyl group, and R 13 and R 14 are each independently a hydrogen atom, a methyl group, a chlorine atom, or a sulfonic acid group.)
前記一般式(I)で表される化合物におけるAが、置換されていてもよいナフチル基であり、Bが、前記一般式(2)で表される基である請求項1に記載のインク。   The ink according to claim 1, wherein A in the compound represented by the general formula (I) is an optionally substituted naphthyl group, and B is a group represented by the general formula (2). 前記一般式(III)で表される化合物におけるDの置換基が、スルホン酸基又はカルボキシル基であり、E及びFが、下記一般式(6)で表される基である請求項1又は2に記載のインク。
Figure 2009030023
(一般式(6)中、R15は、スルホン酸基又はスルホプロポキシ基であり、R16は、水素原子、メチル基、エチル基、メトキシ基、又はエトキシ基のいずれかである。)
The substituent represented by D in the compound represented by the general formula (III) is a sulfonic acid group or a carboxyl group, and E and F are groups represented by the following general formula (6). The ink described in 1.
Figure 2009030023
(In the general formula (6), R 15 is a sulfonic acid group or a sulfopropoxy group, and R 16 is any one of a hydrogen atom, a methyl group, an ethyl group, a methoxy group, or an ethoxy group.)
インク中における前記第1の色材の含有量(質量%)が、インク中における全ての色材の含有量の合計(質量%)に対して、45.0%以上75.0%以下である請求項1乃至3のいずれか1項に記載のインク。   The content (% by mass) of the first color material in the ink is 45.0% or more and 75.0% or less with respect to the total content (% by mass) of all the color materials in the ink. The ink according to any one of claims 1 to 3. インク中における前記第2の色材の含有量(質量%)が、インク中における全ての色材の含有量の合計(質量%)に対して、12.0%より大きく40.0%以下である請求項1乃至4のいずれか1項に記載のインク。   The content (mass%) of the second color material in the ink is greater than 12.0% and 40.0% or less with respect to the total content (mass%) of all the color materials in the ink. The ink according to any one of claims 1 to 4. インク中における前記第1の色材の含有量(質量%)が、インク中における全ての色材の含有量の合計(質量%)に対して50.0%以上であり、
かつ、インク中における前記第2の色材の含有量(質量%)が、インク中における前記第3の色材の含有量(質量%)に対して、質量比率で、0.60倍以上1.00倍未満である請求項1乃至5のいずれか1項に記載のインク。
The content (mass%) of the first color material in the ink is 50.0% or more with respect to the total content (mass%) of all the color materials in the ink,
In addition, the content (mass%) of the second color material in the ink is 0.60 times or more and 1 in mass ratio with respect to the content (mass%) of the third color material in the ink. The ink according to any one of claims 1 to 5, which is less than 0.000 times.
インクをインクジェット方式で吐出して記録媒体に記録を行うインクジェット記録方法において、前記インクが、請求項1乃至のいずれか1項に記載のインクであることを特徴とするインクジェット記録方法。 7. An ink jet recording method for performing recording on a recording medium by ejecting ink by an ink jet method, wherein the ink is the ink according to any one of claims 1 to 6 . インクを収容するインク収容部を備えたインクカートリッジにおいて、前記インクが、請求項1乃至のいずれか1項に記載のインクであることを特徴とするインクカートリッジ。 An ink cartridge comprising an ink container for containing ink, wherein the ink is the ink according to any one of claims 1 to 6 . インクを収容するインク収容部と、インクを吐出するための記録ヘッドとを備えた記録ユニットにおいて、前記インクが、請求項1乃至のいずれか1項に記載のインクであることを特徴とする記録ユニット。 An ink storage portion for storing ink, a recording unit and a recording head for ejecting the ink, the ink, wherein the ink is an ink according to any one of claims 1 to 6 Recording unit. インクを収容するインク収容部と、インクを吐出するための記録ヘッドとを備えたインクジェット記録装置において、前記インクが、請求項1乃至のいずれか1項に記載のインクであることを特徴とするインクジェット記録装置。 An ink jet recording apparatus comprising an ink containing portion for containing ink and a recording head for ejecting ink, wherein the ink is the ink according to any one of claims 1 to 6. Inkjet recording apparatus.
JP2008142279A 2007-07-05 2008-05-30 Ink, ink jet recording method, ink cartridge, recording unit, and ink jet recording apparatus Active JP4632459B2 (en)

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JP2008142279A JP4632459B2 (en) 2007-07-05 2008-05-30 Ink, ink jet recording method, ink cartridge, recording unit, and ink jet recording apparatus
US12/136,393 US7550037B2 (en) 2007-07-05 2008-06-10 Ink, ink jet recording method, ink cartridge, recording unit and ink jet recording apparatus
EP08158847A EP2011841B1 (en) 2007-07-05 2008-06-24 Ink, ink jet recording method, ink cartridge, recording unit and ink jet recording apparatus
CN2008101080633A CN101338094B (en) 2007-07-05 2008-07-04 Ink, ink jet recording method, ink cartridge, recording unit and ink jet recording apparatus

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JP4632459B2 (en) * 2007-07-05 2011-02-16 キヤノン株式会社 Ink, ink jet recording method, ink cartridge, recording unit, and ink jet recording apparatus
WO2009136576A1 (en) * 2008-05-07 2009-11-12 日本化薬株式会社 Trisazo compound, ink composition, recording method and coloring material
JP5456666B2 (en) * 2008-05-07 2014-04-02 日本化薬株式会社 Trisazo compound, ink composition, recording method and colored body
JP5570506B2 (en) * 2009-06-12 2014-08-13 日本化薬株式会社 Ink composition, ink jet recording method, and colored body
WO2011086974A1 (en) * 2010-01-12 2011-07-21 日本化薬株式会社 Ink composition, inkjet recording method and colored body
JP2012072373A (en) 2010-08-31 2012-04-12 Fujifilm Corp Ink
JP5663255B2 (en) * 2010-09-29 2015-02-04 富士フイルム株式会社 Ink set, ink cartridge, ink jet printer, ink jet recording method and recorded matter
JP5757714B2 (en) * 2010-09-30 2015-07-29 富士フイルム株式会社 Ink composition, ink jet recording method using the same, and recorded matter
JP2012211293A (en) 2011-03-18 2012-11-01 Fujifilm Corp Ink composition, inkjet recording ink, and inkjet recording method
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JP3412857B2 (en) * 1992-05-13 2003-06-03 キヤノン株式会社 Ink, image forming method, inkjet recording method, inkjet recording unit, ink cartridge, and inkjet recording apparatus
KR20010020220A (en) * 1997-04-24 2001-03-15 다께다 가즈히꼬 Water-soluble trisazo compounds, aqueous ink composition and colored article
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JP5144895B2 (en) * 2005-05-27 2013-02-13 富士フイルム株式会社 Ink jet recording ink, ink set, and ink jet recording method
JP5238155B2 (en) * 2005-10-20 2013-07-17 富士フイルム株式会社 Ink composition, ink set, and recording method
US7758683B2 (en) * 2005-10-20 2010-07-20 Fujifilm Corporation Ink composition, ink set and recording method
JP4977371B2 (en) * 2005-10-20 2012-07-18 富士フイルム株式会社 Ink set, ink cartridge, ink jet printer, ink jet recording method, recorded matter, and fading improvement method
CN101346437B (en) * 2006-01-06 2012-01-11 日本化药株式会社 Trisazo compound, ink composition, recording method and colored matter
JP4577265B2 (en) * 2006-05-12 2010-11-10 セイコーエプソン株式会社 Black ink composition, ink set, ink cartridge, ink jet recording method and recorded matter
JP4632459B2 (en) * 2007-07-05 2011-02-16 キヤノン株式会社 Ink, ink jet recording method, ink cartridge, recording unit, and ink jet recording apparatus

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