WO2005030887A1 - インク組成物 - Google Patents
インク組成物 Download PDFInfo
- Publication number
- WO2005030887A1 WO2005030887A1 PCT/JP2004/014351 JP2004014351W WO2005030887A1 WO 2005030887 A1 WO2005030887 A1 WO 2005030887A1 JP 2004014351 W JP2004014351 W JP 2004014351W WO 2005030887 A1 WO2005030887 A1 WO 2005030887A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- ink composition
- salt
- general formula
- heterocyclic
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
Definitions
- a plurality of color ink compositions are prepared and a color image is formed by inkjet recording.
- a color image is formed by three colors of a yellow ink composition, a magenta ink composition, and a cyan ink composition, and in some cases, four colors obtained by adding a black ink composition.
- a color image may be formed with six colors obtained by adding a light cyan ink composition and a light magenta ink composition to these four colors or seven colors obtained by further adding a dark yellow ink composition.
- the ink composition used for forming such a color image in addition to having good color developing properties itself, develops a good intermediate color when combined with a plurality of ink compositions. In addition, it is required that the printed matter does not discolor or fade during subsequent storage.
- Patent Document 2 Japanese Patent Application Laid-Open No. 2001-288392
- Patent Document 3 JP-A-2002-371214
- the inventors of the present invention conducted further investigations on the clogging resistance, light resistance, gas resistance, and moisture resistance of various magenta dyes. As a result, the ink composition containing a specific magenta dye was obtained.
- an aromatic compound having a carboxyl group and Z or a salt thereof are added to the above, compatibility of these properties is observed.
- the salt of the compound having a carboxyl group to be added is a lithium salt, the eye-resistance is high. It has been found that the effect of improving the clogging property is remarkably excellent, and the present invention has been completed based on these findings.
- the ink composition according to the present invention is characterized in that the compound represented by the general formula (1) and a salt thereof are a compound represented by the following general formula (2) and a salt thereof.
- the ink composition according to the present invention is characterized in that the compound having a naphthalene skeleton and the salt thereof described in 4 above are a compound having a carboxyl group at the 2-position and a salt thereof.
- A represents a residue of a 5-membered heterocyclic diazo component A—NH.
- the aryloxycarbol group includes an aryloxycarbol group having a substituent and an unsubstituted aryloxycarbol group.
- the aryloxycarbonyl group is preferably an aryloxycarbonyl group having 7 to 12 carbon atoms.
- the substituent includes an ionic hydrophilic group. Examples of the aryloxycarbonyl group include a phenoxycarbol group.
- the alkyl and arylsulfonyl groups include substituted alkyl and arylsulfonyl groups and unsubstituted alkyl and arylsulfonyl groups.
- a sulfonylamino group having 1 to 12 carbon atoms is preferable.
- the substituent include an ionic hydrophilic group.
- Examples of the alkyl and arylsulfur groups include a methanesulfol group and a phenylsulfol group, respectively.
- Examples of the alkyl and arylsulfyl groups include a methanesulfyl group and a phenylsulfyl group, respectively.
- the sulfamoyl group includes a sulfamoyl group having a substituent and an unsubstituted sulfamoyl group.
- Examples of the substituent include an alkyl group.
- Examples of the sulfamoyl group include a dimethylsulfamoyl group and a di (2-hydroxyethyl) sulfamoyl group.
- Each group described in the general formula (2) may further have a substituent.
- the substituent constant ⁇ ⁇ value used in the present specification will be described in relation to the substituent Z 1 .
- the No-Met rule is an empirical rule proposed by LP Hammett in 1935 to quantitatively discuss the effect of substituents on the reaction or equilibrium of benzene derivatives, but it is widely accepted today.
- the substituent constants determined by Hammett's rule include the ⁇ ⁇ value and the ⁇ m value, and these values can be found in many general books.For example, JA Dean, “Lange's Handbook of Chemistry, 12th edition, 1979 (McGraw-Hill) and the special edition of “Danigaku no Gaku”, No. 122, pp. 96-103, 1979 (Nankodo).
- each substituent is defined or explained by Hammett's substituent constant ⁇ ⁇ , but this is limited to only those substituents having a value known in the literature, which can be found in the above-mentioned books. It goes without saying that even if the value is unknown in the literature, it also includes substituents that would be included in the range when measured according to the Met rule.
- the ⁇ ⁇ value is used as a measure of the electronic effect of the substituent, regardless of the substitution position. . In the present invention, the ⁇ ⁇ value is used in this sense.
- Electron-withdrawing groups having a Hammett substituent constant ⁇ ⁇ value of 0.30 or more include, in addition to the above, Roxy group (for example, acetoxy), carbamoyl group (for example, N-ethylcarbamoyl, N, N-dibutylcarbamoyl), halogenated alkoxy group (for example, trifluoromethyloxy), halogenated aryloxy group (for example, pentafluorophenyl) -Roxy), sulfo-roxy group (for example, methylsulfo-roxy group), halogenated alkylthio group (for example, difluoromethylthio), and two or more substituted with electron-withdrawing groups having a ⁇ p value of 0.15 or more.
- Roxy group for example, acetoxy
- carbamoyl group for example, N-ethylcarbamoyl, N, N-dibutylcarbamo
- (C) ⁇ is preferably a pyrazole ring, an imidazole ring, an isothiazole ring, a thiadiazole ring, or a benzothiazole ring, more preferably a pyrazole ring or an isothiazole ring, and most preferably a pyrazole ring.
- the compound in which at least one of the various substituents is the above-mentioned preferable group is more preferable than the compound having more various substituents.
- All substituents more preferred by compounds wherein the group is the preferred group are Preferably, the compound that is the group is most preferred.
- step (c) In the presence of a base, the compound formed in the above step (b) is reacted with an alkylating agent, an arylating agent or a heterylating agent to introduce a substituent such as an alkyl group into the above general formula ( The compound represented by 1) is formed.
- the compound represented by the general formula (1) and a carboxyl group The content ratio of at least one selected from aromatic compounds and salts thereof having the formula (I) is preferably in the range of 4: 1 to 1:10, more preferably in the range of 3: 1 to 1: 8 by weight of the total amount. I prefer that.
- Aromatic compound having a carboxyl group and its salt power By setting at least one kind of ratio to be selected to be higher than 4: 1, a sufficient effect of improving moisture resistance can be obtained, and also to be lower than 1:10. This makes it possible to easily secure the reliability of clogging.
- Example 11 The ink composition of Example 10 exhibited good quality of a certain level or more in any property.However, when a compound having a naphthalene skeleton and having a carboxyl group at the 2-position was used (Example 7) — 10) is better than the case where the aromatic compound having a carboxyl group does not have a naphthalene skeleton (Examples 14 to 14) and the case where the aromatic compound has a naphthalene skeleton but the carboxyl group is not at the 2-position (Examples 5 and 6). High moisture resistance. In addition, the lithium salt (Examples 9, 9) was better than the case where the sodium salt of an aromatic compound having a carboxyl group was used (Examples 7, 8). ) Is more resistant to clogging
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP20040788379 EP1676892B1 (en) | 2003-09-30 | 2004-09-30 | Ink composition |
CN2004800351021A CN1886472B (zh) | 2003-09-30 | 2004-09-30 | 油墨组合物 |
US10/573,798 US7435292B2 (en) | 2003-09-30 | 2004-09-30 | Ink composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003339688A JP4515738B2 (ja) | 2003-09-30 | 2003-09-30 | インク組成物 |
JP2003-339688 | 2003-09-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005030887A1 true WO2005030887A1 (ja) | 2005-04-07 |
Family
ID=34386184
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2004/014351 WO2005030887A1 (ja) | 2003-09-30 | 2004-09-30 | インク組成物 |
Country Status (5)
Country | Link |
---|---|
US (1) | US7435292B2 (ja) |
EP (1) | EP1676892B1 (ja) |
JP (1) | JP4515738B2 (ja) |
CN (1) | CN1886472B (ja) |
WO (1) | WO2005030887A1 (ja) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1749864A1 (en) * | 2004-05-28 | 2007-02-07 | Seiko Epson Corporation | Ink composition, method of ink-jet recording with the same, and print |
US7479178B2 (en) | 2006-02-06 | 2009-01-20 | Hewlett-Packard Development Company, L.P. | Dye sets for inkjet imaging and ink sets using the same |
WO2009110554A1 (ja) * | 2008-03-07 | 2009-09-11 | 富士フイルム株式会社 | アゾ顔料、顔料分散物、着色組成物、及びインクジェット記録用インク |
WO2009110553A1 (ja) * | 2008-03-07 | 2009-09-11 | 富士フイルム株式会社 | アゾ顔料、該アゾ顔料を含む顔料分散物及び着色組成物 |
US7708820B2 (en) | 2004-07-13 | 2010-05-04 | Fujifilm Corporation | Black ink composition, ink set containing the same, and ink jet recording method |
AU2004316426B2 (en) * | 2004-01-28 | 2010-08-19 | Irobot Corporation | Debris sensor for cleaning apparatus |
US20100255275A1 (en) * | 2007-09-29 | 2010-10-07 | Gavin Wright | Magenta Dyes and Inks for Use in Ink-Jet Printing |
US20110262716A1 (en) * | 2008-12-20 | 2011-10-27 | Fujifilm Corporation | Magenta Dyes and Inks for Use in Ink-Jet Printing |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5124093B2 (ja) * | 2006-01-20 | 2013-01-23 | 富士フイルム株式会社 | インク、インクジェット用インク、インクジェット記録インクセット、インクジェット記録方法着色画像材料の耐候性改良方法 |
GB0812721D0 (en) * | 2008-07-11 | 2008-08-20 | Fujifilm Imaging Colorants Ltd | Magenta dyes and inks for use in ink-jet printing |
WO2010070312A2 (en) * | 2008-12-20 | 2010-06-24 | Fujifilm Imaging Colorants Limited | Magenta dyes and inks for use in ink-jet printing |
GB0910806D0 (en) * | 2009-06-23 | 2009-08-05 | Fujifilm Imaging Colorants Ltd | Magenta dyes and inks for use in ink-jet printing |
US8496743B2 (en) * | 2010-03-18 | 2013-07-30 | Seiko Epson Corporation | Ink composition |
JP6550830B2 (ja) * | 2015-03-25 | 2019-07-31 | セイコーエプソン株式会社 | 機能層形成用組成物、機能層形成用組成物の製造方法、有機el素子の製造方法、有機el装置、電子機器 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10152635A (ja) | 1996-09-24 | 1998-06-09 | Seiko Epson Corp | カラーインクジェット記録方法 |
JP2000289322A (ja) | 1999-04-06 | 2000-10-17 | Seiko Epson Corp | にじみのない画像を形成可能なインクジェット記録方法 |
JP2000290559A (ja) | 1999-04-08 | 2000-10-17 | Seiko Epson Corp | インク及びインクジェット記録方法 |
JP2001288392A (ja) | 2000-04-07 | 2001-10-16 | Seiko Epson Corp | インクセット |
JP2002371214A (ja) | 2001-04-09 | 2002-12-26 | Fuji Photo Film Co Ltd | 画像形成用着色組成物、インクジェット記録用インク、インクジェット記録方法、感熱記録材料、カラートナー、およびカラーフィルター |
JP2002371079A (ja) | 2001-04-09 | 2002-12-26 | Fuji Photo Film Co Ltd | アゾ化合物及びその製造方法 |
JP2003231845A (ja) | 2002-02-12 | 2003-08-19 | Fuji Photo Film Co Ltd | インクジェット記録用インク及びインクジェット記録方法 |
JP2003246942A (ja) | 2002-02-26 | 2003-09-05 | Fuji Photo Film Co Ltd | 着色組成物、インク、インクジェット記録方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5707432A (en) * | 1996-06-14 | 1998-01-13 | Cabot Corporation | Modified carbon products and inks and coatings containing modified carbon products |
JP3903938B2 (ja) * | 2002-04-23 | 2007-04-11 | セイコーエプソン株式会社 | インク組成物、それを用いたインクジェット記録方法および記録物 |
JP4433664B2 (ja) * | 2002-08-30 | 2010-03-17 | セイコーエプソン株式会社 | インク組成物及びインクジェット記録方法 |
JP4186775B2 (ja) * | 2003-09-30 | 2008-11-26 | セイコーエプソン株式会社 | インクセット |
US7323045B2 (en) * | 2003-09-30 | 2008-01-29 | Seiko Epson Corporation | Magenta ink composition |
-
2003
- 2003-09-30 JP JP2003339688A patent/JP4515738B2/ja not_active Expired - Fee Related
-
2004
- 2004-09-30 CN CN2004800351021A patent/CN1886472B/zh not_active Expired - Fee Related
- 2004-09-30 US US10/573,798 patent/US7435292B2/en not_active Expired - Fee Related
- 2004-09-30 WO PCT/JP2004/014351 patent/WO2005030887A1/ja active Application Filing
- 2004-09-30 EP EP20040788379 patent/EP1676892B1/en not_active Expired - Lifetime
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10152635A (ja) | 1996-09-24 | 1998-06-09 | Seiko Epson Corp | カラーインクジェット記録方法 |
JP2000289322A (ja) | 1999-04-06 | 2000-10-17 | Seiko Epson Corp | にじみのない画像を形成可能なインクジェット記録方法 |
JP2000290559A (ja) | 1999-04-08 | 2000-10-17 | Seiko Epson Corp | インク及びインクジェット記録方法 |
JP2001288392A (ja) | 2000-04-07 | 2001-10-16 | Seiko Epson Corp | インクセット |
JP2002371214A (ja) | 2001-04-09 | 2002-12-26 | Fuji Photo Film Co Ltd | 画像形成用着色組成物、インクジェット記録用インク、インクジェット記録方法、感熱記録材料、カラートナー、およびカラーフィルター |
JP2002371079A (ja) | 2001-04-09 | 2002-12-26 | Fuji Photo Film Co Ltd | アゾ化合物及びその製造方法 |
JP2003231845A (ja) | 2002-02-12 | 2003-08-19 | Fuji Photo Film Co Ltd | インクジェット記録用インク及びインクジェット記録方法 |
JP2003246942A (ja) | 2002-02-26 | 2003-09-05 | Fuji Photo Film Co Ltd | 着色組成物、インク、インクジェット記録方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP1676892A4 |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2004316426B2 (en) * | 2004-01-28 | 2010-08-19 | Irobot Corporation | Debris sensor for cleaning apparatus |
EP1749864A1 (en) * | 2004-05-28 | 2007-02-07 | Seiko Epson Corporation | Ink composition, method of ink-jet recording with the same, and print |
US7871465B2 (en) | 2004-05-28 | 2011-01-18 | Seiko Epson Corporation | Ink composition, and ink jet recording method and recorded matter using the same |
EP1749864A4 (en) * | 2004-05-28 | 2009-05-06 | Seiko Epson Corp | INK COMPOSITION, ITEM USED IN METHOD FOR INK RADIATION RECORDING AND PRINTING |
US7708820B2 (en) | 2004-07-13 | 2010-05-04 | Fujifilm Corporation | Black ink composition, ink set containing the same, and ink jet recording method |
US7479178B2 (en) | 2006-02-06 | 2009-01-20 | Hewlett-Packard Development Company, L.P. | Dye sets for inkjet imaging and ink sets using the same |
US20100255275A1 (en) * | 2007-09-29 | 2010-10-07 | Gavin Wright | Magenta Dyes and Inks for Use in Ink-Jet Printing |
JP2009235381A (ja) * | 2008-03-07 | 2009-10-15 | Fujifilm Corp | アゾ顔料、顔料分散物、着色組成物、及びインクジェット記録用インク |
WO2009110553A1 (ja) * | 2008-03-07 | 2009-09-11 | 富士フイルム株式会社 | アゾ顔料、該アゾ顔料を含む顔料分散物及び着色組成物 |
WO2009110554A1 (ja) * | 2008-03-07 | 2009-09-11 | 富士フイルム株式会社 | アゾ顔料、顔料分散物、着色組成物、及びインクジェット記録用インク |
US8177861B2 (en) | 2008-03-07 | 2012-05-15 | Fujifilm Corporation | AZO pigment, pigment dispersion containing the AZO pigment, and coloring composition |
US8206465B2 (en) | 2008-03-07 | 2012-06-26 | Fujifilm Corporation | Azo pigments, pigment dispersion, coloring composition, and ink for inkjet recording |
US20110262716A1 (en) * | 2008-12-20 | 2011-10-27 | Fujifilm Corporation | Magenta Dyes and Inks for Use in Ink-Jet Printing |
Also Published As
Publication number | Publication date |
---|---|
EP1676892A1 (en) | 2006-07-05 |
CN1886472A (zh) | 2006-12-27 |
JP4515738B2 (ja) | 2010-08-04 |
US20070146453A1 (en) | 2007-06-28 |
US7435292B2 (en) | 2008-10-14 |
EP1676892B1 (en) | 2013-03-27 |
EP1676892A4 (en) | 2006-09-27 |
CN1886472B (zh) | 2010-06-02 |
JP2005105108A (ja) | 2005-04-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4186775B2 (ja) | インクセット | |
EP2022830B1 (en) | Magenta ink composition, ink set, ink cartridge, inkjet recording method and recorded matter | |
US7465347B2 (en) | Yellow ink composition, ink set, ink cartridge, inkjet recording method, and recorded matter | |
JP5099295B2 (ja) | インクジェット記録用マゼンタインク | |
US7323045B2 (en) | Magenta ink composition | |
JP4515738B2 (ja) | インク組成物 | |
JP4400187B2 (ja) | 黒色水性インク組成物 | |
JP4729842B2 (ja) | マゼンタインク組成物 | |
JP5099296B2 (ja) | インクジェット記録用マゼンタインク | |
JP5099297B2 (ja) | インクジェット記録用マゼンタインク | |
US7871465B2 (en) | Ink composition, and ink jet recording method and recorded matter using the same | |
JP4701635B2 (ja) | インク組成物、それを用いたインクジェット記録方法および記録物 | |
JP2003183545A (ja) | 黒色水性インク組成物、それを用いたインクジェット記録方法および記録物 | |
JP2011195782A (ja) | インク組成物 | |
JP4179126B2 (ja) | マゼンタインク組成物 | |
JP2005146228A (ja) | インクセット | |
JP2011042798A (ja) | マゼンタインク組成物 | |
JP2006083339A (ja) | インク組成物 | |
JP2005281378A (ja) | インクセット | |
JP4432431B2 (ja) | インクセット | |
JP5871198B2 (ja) | インク組成物 | |
JP2003286422A (ja) | 黒色水性インク組成物、それを用いたインクジェット記録方法および記録物 | |
JP2008248173A (ja) | インク組成物、記録方法及び記録物 | |
JP2005047987A (ja) | 黒色インク組成物 | |
JP2010043266A (ja) | 黒色水性インク組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200480035102.1 Country of ref document: CN |
|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2004788379 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 2004788379 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2007146453 Country of ref document: US Ref document number: 10573798 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 10573798 Country of ref document: US |