CA2461432A1 - Novel anthrapyridone compounds, water-base magenta ink compositions, and ink-jet recording process - Google Patents
Novel anthrapyridone compounds, water-base magenta ink compositions, and ink-jet recording process Download PDFInfo
- Publication number
- CA2461432A1 CA2461432A1 CA002461432A CA2461432A CA2461432A1 CA 2461432 A1 CA2461432 A1 CA 2461432A1 CA 002461432 A CA002461432 A CA 002461432A CA 2461432 A CA2461432 A CA 2461432A CA 2461432 A1 CA2461432 A1 CA 2461432A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- optionally substituted
- sulfonic acid
- ink
- jet recording
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/14—Benz-azabenzanthrones (anthrapyridones)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/043—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring containing two or more triazine rings linked together by a non-chromophoric link
-
- 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
Abstract
New anthrapyridone compounds represented by the general formula (14):
(see formula 14) {wherein R represents a hydrogen atom, an alkyl group (optionally substituted with mono- or di-alkylamino group), a lower alkyl group(optionally substituted with a hydroxyl group or a cyano group), or a cyclohexyl group;
Y represents a chlorine atom, a hydroxyl group, an amino group, mono- or di-alkylamino group (optionally substituted with a sulfonic acid group, a carboxy group, or a hydroxyl group), an aralkyl- or cycloalkyl- amino group, an alkoxy group, a phenoxy group (optionally substituted with a sulfonic acid group, a carboxy group, an acetylamino group, an amino group, or a hydroxyl group), an anilino group (optionally substituted with a sulfonic acid group or a carboxy group), or a naphthylamino group (optionally substituted with a sulfonic acid group); and X represents a bridging group); or salts thereof and magenta inks containing the same, which have hues and vividness suitable for ink-jet recording and give records excellent in fastness to light, gas, water and so on.
(see formula 14) {wherein R represents a hydrogen atom, an alkyl group (optionally substituted with mono- or di-alkylamino group), a lower alkyl group(optionally substituted with a hydroxyl group or a cyano group), or a cyclohexyl group;
Y represents a chlorine atom, a hydroxyl group, an amino group, mono- or di-alkylamino group (optionally substituted with a sulfonic acid group, a carboxy group, or a hydroxyl group), an aralkyl- or cycloalkyl- amino group, an alkoxy group, a phenoxy group (optionally substituted with a sulfonic acid group, a carboxy group, an acetylamino group, an amino group, or a hydroxyl group), an anilino group (optionally substituted with a sulfonic acid group or a carboxy group), or a naphthylamino group (optionally substituted with a sulfonic acid group); and X represents a bridging group); or salts thereof and magenta inks containing the same, which have hues and vividness suitable for ink-jet recording and give records excellent in fastness to light, gas, water and so on.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001/292853 | 2001-09-26 | ||
JP2001292853 | 2001-09-26 | ||
PCT/JP2002/009874 WO2003027185A1 (en) | 2001-09-26 | 2002-09-25 | Novel anthrapyridone compounds, water-base magenta ink compositions, and ink-jet recording process |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2461432A1 true CA2461432A1 (en) | 2003-04-03 |
CA2461432C CA2461432C (en) | 2009-04-14 |
Family
ID=19114742
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002461432A Expired - Lifetime CA2461432C (en) | 2001-09-26 | 2002-09-25 | Novel anthrapyridone compounds, water-base magenta ink compositions, and ink-jet recording process |
Country Status (9)
Country | Link |
---|---|
US (2) | US6929361B2 (en) |
EP (1) | EP1437385B1 (en) |
KR (2) | KR100620408B1 (en) |
CN (1) | CN1303161C (en) |
CA (1) | CA2461432C (en) |
DE (1) | DE60212423T2 (en) |
RU (1) | RU2281944C2 (en) |
TW (1) | TWI265182B (en) |
WO (1) | WO2003027185A1 (en) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4433664B2 (en) * | 2002-08-30 | 2010-03-17 | セイコーエプソン株式会社 | Ink composition and inkjet recording method |
TWI336346B (en) * | 2003-05-22 | 2011-01-21 | Nippon Kayaku Kk | Anthrapyridone compound, aqueous magenta ink composition and ink-jet recording method |
TWI336347B (en) * | 2003-05-22 | 2011-01-21 | Nippon Kayaku Kk | Novel anthrapyridone compound, aqueous magenta ink composition and ink-jet recording method |
US7323045B2 (en) * | 2003-09-30 | 2008-01-29 | Seiko Epson Corporation | Magenta ink composition |
JP4186775B2 (en) * | 2003-09-30 | 2008-11-26 | セイコーエプソン株式会社 | Ink set |
EP2455431B1 (en) * | 2003-10-23 | 2013-08-21 | Fujifilm Corporation | Ink and ink set for inkjet recording |
JP4604478B2 (en) * | 2003-11-19 | 2011-01-05 | コニカミノルタホールディングス株式会社 | NOVEL DYE, COLORING COMPOSITION, INKJET RECORDING LIQUID, AND INKJET RECORDING METHOD |
JP3793222B2 (en) * | 2004-07-02 | 2006-07-05 | キヤノン株式会社 | Ink jet ink, ink set, ink jet recording method, ink cartridge, recording unit, and ink jet recording apparatus |
JP3793223B2 (en) * | 2004-07-02 | 2006-07-05 | キヤノン株式会社 | Ink jet ink, ink jet recording method, ink cartridge, recording unit, and ink jet recording apparatus |
JP4794940B2 (en) * | 2004-08-04 | 2011-10-19 | キヤノン株式会社 | INK TANK, INK JET RECORDING METHOD, AND INK TANK REPRODUCING METHOD |
JP3907671B2 (en) * | 2004-08-31 | 2007-04-18 | キヤノン株式会社 | Ink jet ink, ink jet ink preparation method, ink jet recording method, and ink cartridge |
JP4989975B2 (en) * | 2005-01-17 | 2012-08-01 | 日本化薬株式会社 | Anthrapyridone compound, magenta ink composition and colored body |
GB0509342D0 (en) * | 2005-05-06 | 2005-06-15 | Avecia Inkjet Ltd | Colorants and their use in ink jet printing |
JP4631793B2 (en) * | 2006-05-12 | 2011-02-16 | セイコーエプソン株式会社 | Magenta ink composition, ink set, ink cartridge, ink jet recording method and recorded matter |
JP4465721B2 (en) * | 2006-09-29 | 2010-05-19 | セイコーエプソン株式会社 | Ink set, ink cartridge, ink jet recording method and recorded matter |
JP4548398B2 (en) * | 2006-09-29 | 2010-09-22 | セイコーエプソン株式会社 | Ink set, ink cartridge, ink jet recording method and recorded matter |
US7785411B2 (en) * | 2006-11-09 | 2010-08-31 | Nippon Kayaku Kabushiki Kaisha | Anthrapyridone compound or salt thereof, magenta ink composition and colored product |
WO2008066024A1 (en) * | 2006-11-29 | 2008-06-05 | Nippon Kayaku Kabushiki Kaisha | Anthrapyridone compound, salt thereof, magenta ink composition and colored body |
JP5145243B2 (en) * | 2006-12-01 | 2013-02-13 | 日本化薬株式会社 | Anthrapyridone compound, salt thereof, magenta ink composition containing the same, and colored product |
JP4457412B2 (en) * | 2006-12-14 | 2010-04-28 | セイコーエプソン株式会社 | Ink set, ink cartridge, ink jet recording method and recorded matter |
US7618484B2 (en) * | 2007-05-01 | 2009-11-17 | Canon Kabushiki Kaisha | Ink jet ink, ink jet recording method, ink cartridge, recording unit and ink jet recording apparatus |
JP2009132891A (en) | 2007-10-31 | 2009-06-18 | Fujifilm Corp | Ink set, inkjet recording method and recorded matter |
WO2009093433A1 (en) * | 2008-01-25 | 2009-07-30 | Nippon Kayaku Kabushiki Kaisha | Anthrapyridone compound or salt thereof, magenta ink composition containing the anthrapyridone compound, and colored body |
JP5451556B2 (en) * | 2009-09-18 | 2014-03-26 | キヤノン株式会社 | Dye compound |
JP5785799B2 (en) | 2010-07-30 | 2015-09-30 | 富士フイルム株式会社 | Novel azo compound, aqueous solution, ink composition, ink for ink jet recording, ink jet recording method, ink cartridge for ink jet recording, and ink jet recorded matter |
JP5866150B2 (en) | 2010-07-30 | 2016-02-17 | 富士フイルム株式会社 | Novel azo compound, aqueous solution, ink composition, ink for ink jet recording, ink jet recording method, ink cartridge for ink jet recording, and ink jet recorded matter |
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 |
JP5854207B2 (en) * | 2011-11-28 | 2016-02-09 | セイコーエプソン株式会社 | Ink set |
EP2799498B1 (en) | 2011-12-26 | 2019-05-01 | Fujifilm Corporation | Compound having xanthene skeleton, coloring composition, ink for ink jet printing, and ink jet printing method |
WO2013129265A1 (en) | 2012-02-29 | 2013-09-06 | 富士フイルム株式会社 | Colored composition, inkjet recording ink, and inkjet recording method |
JP2014198816A (en) | 2012-09-26 | 2014-10-23 | 富士フイルム株式会社 | Azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording, and inkjet recorded matter |
EP3015516A4 (en) | 2013-08-08 | 2016-11-02 | Nippon Kayaku Kk | Ink composition, ink jet recording method using same, and colored material |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2759939A (en) * | 1956-08-21 | Seriesand the preparation | ||
JPS5674173A (en) | 1979-11-22 | 1981-06-19 | Toshiba Corp | Preparation of strontium halophosphate fluorescent material |
JPS5974173A (en) | 1982-10-22 | 1984-04-26 | Nippon Kayaku Co Ltd | Red water-base ink |
JPH0216171A (en) | 1988-07-05 | 1990-01-19 | Ricoh Co Ltd | Water-base ink |
EP0927747B1 (en) * | 1996-09-11 | 2006-07-19 | Nippon Kayaku Kabushiki Kaisha | Anthrapyridone compounds, water-base ink composition, and articles colored therewith |
JP3957423B2 (en) | 1998-03-10 | 2007-08-15 | 日本化薬株式会社 | Aqueous magenta ink composition and ink jet recording method |
JP3767879B2 (en) | 1998-03-25 | 2006-04-19 | 日本化薬株式会社 | Novel anthrapyridone compound, aqueous magenta ink composition and ink jet recording method |
KR100580937B1 (en) | 1998-03-25 | 2006-05-17 | 니폰 카야쿠 가부시키가이샤 | Novel anthrapyridone compounds, water-based magenta ink composition, and method of ink-jet recording |
JP4162318B2 (en) * | 1999-03-04 | 2008-10-08 | 日本化薬株式会社 | Water-based ink set, coloring method and colored body thereof |
JP4411856B2 (en) * | 2002-04-23 | 2010-02-10 | セイコーエプソン株式会社 | Ink set |
JP4433664B2 (en) * | 2002-08-30 | 2010-03-17 | セイコーエプソン株式会社 | Ink composition and inkjet recording method |
-
2002
- 2002-09-25 RU RU2004108852/04A patent/RU2281944C2/en not_active IP Right Cessation
- 2002-09-25 CN CNB028189566A patent/CN1303161C/en not_active Expired - Fee Related
- 2002-09-25 DE DE60212423T patent/DE60212423T2/en not_active Expired - Lifetime
- 2002-09-25 EP EP02768063A patent/EP1437385B1/en not_active Expired - Lifetime
- 2002-09-25 KR KR1020047004253A patent/KR100620408B1/en active IP Right Grant
- 2002-09-25 KR KR1020067007732A patent/KR100635705B1/en not_active IP Right Cessation
- 2002-09-25 CA CA002461432A patent/CA2461432C/en not_active Expired - Lifetime
- 2002-09-25 US US10/490,400 patent/US6929361B2/en not_active Expired - Lifetime
- 2002-09-25 TW TW091121958A patent/TWI265182B/en not_active IP Right Cessation
- 2002-09-25 WO PCT/JP2002/009874 patent/WO2003027185A1/en active IP Right Grant
-
2005
- 2005-04-01 US US11/096,507 patent/US7015327B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US20040239739A1 (en) | 2004-12-02 |
KR20060054487A (en) | 2006-05-22 |
KR100620408B1 (en) | 2006-09-13 |
EP1437385A4 (en) | 2005-01-26 |
TWI265182B (en) | 2006-11-01 |
EP1437385A1 (en) | 2004-07-14 |
CN1558933A (en) | 2004-12-29 |
DE60212423T2 (en) | 2006-10-19 |
RU2004108852A (en) | 2005-09-20 |
CN1303161C (en) | 2007-03-07 |
DE60212423D1 (en) | 2006-07-27 |
US6929361B2 (en) | 2005-08-16 |
US7015327B2 (en) | 2006-03-21 |
US20050171351A1 (en) | 2005-08-04 |
WO2003027185A1 (en) | 2003-04-03 |
KR20040044978A (en) | 2004-05-31 |
EP1437385B1 (en) | 2006-06-14 |
KR100635705B1 (en) | 2006-10-17 |
CA2461432C (en) | 2009-04-14 |
RU2281944C2 (en) | 2006-08-20 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry |
Effective date: 20220926 |