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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- JP
- Japan
- Prior art keywords
- group
- ink
- carbon atoms
- sulfonic acid
- carboxyl
- 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.)
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- 125000004432 carbon atoms Chemical group C* 0.000 claims 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 14
- 125000000542 sulfonic acid group Chemical group 0.000 claims 13
- 239000000463 material Substances 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 6
- 150000001875 compounds Chemical group 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- -1 carbamoyloxy group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000003086 colorant Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 0 CC([C@](C(Nc1ccc(*)cc1)N=C1Nc2ccc(*)cc2)N=NBN=N*)=C1C#N Chemical compound CC([C@](C(Nc1ccc(*)cc1)N=C1Nc2ccc(*)cc2)N=NBN=N*)=C1C#N 0.000 description 8
Claims (10)
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。
(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。)
(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。)
(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。)
(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).
(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.)
(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.)
(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.)
(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.)
(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.
(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.)
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.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007177459 | 2007-07-05 | ||
JP2008142279A JP4632459B2 (en) | 2007-07-05 | 2008-05-30 | Ink, ink jet recording method, ink cartridge, recording unit, and ink jet recording apparatus |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2009030023A JP2009030023A (en) | 2009-02-12 |
JP2009030023A5 true JP2009030023A5 (en) | 2010-06-03 |
JP4632459B2 JP4632459B2 (en) | 2011-02-16 |
Family
ID=40212266
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2008142279A Active JP4632459B2 (en) | 2007-07-05 | 2008-05-30 | Ink, ink jet recording method, ink cartridge, recording unit, and ink jet recording apparatus |
Country Status (2)
Country | Link |
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JP (1) | JP4632459B2 (en) |
CN (1) | CN101338094B (en) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
WO2016136562A1 (en) * | 2015-02-27 | 2016-09-01 | 富士フイルム株式会社 | Azo compound, coloring composition, ink for inkjet recording, inkjet recording method, inkjet printer cartridge and inkjet recorded matter |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
JP5085129B2 (en) * | 2004-06-23 | 2012-11-28 | 日本化薬株式会社 | Azo compound, ink composition and colored body |
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 |
-
2008
- 2008-05-30 JP JP2008142279A patent/JP4632459B2/en active Active
- 2008-07-04 CN CN2008101080633A patent/CN101338094B/en active Active
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