CA2600803A1 - Amine- and phthalocyanine dye-containing ink-jet inks with improved ozone fastness - Google Patents

Amine- and phthalocyanine dye-containing ink-jet inks with improved ozone fastness Download PDF

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Publication number
CA2600803A1
CA2600803A1 CA002600803A CA2600803A CA2600803A1 CA 2600803 A1 CA2600803 A1 CA 2600803A1 CA 002600803 A CA002600803 A CA 002600803A CA 2600803 A CA2600803 A CA 2600803A CA 2600803 A1 CA2600803 A1 CA 2600803A1
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CA
Canada
Prior art keywords
ink
jet ink
jet
amine additive
phthalocyanine dye
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
Application number
CA002600803A
Other languages
French (fr)
Other versions
CA2600803C (en
Inventor
John R. Moffatt
Linda Uhlir-Tsang
Joseph W. Tsang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hewlett Packard Development Co LP
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2600803A1 publication Critical patent/CA2600803A1/en
Application granted granted Critical
Publication of CA2600803C publication Critical patent/CA2600803C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • 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
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes

Abstract

In accordance with embodiments of the present invention, an ink-jet ink can comprise a metallized phthalocyanine dye and a liquid vehicle carrying the dye. The liquid vehicle can include an amine additive present in the ink-jet ink at an effective concentration to cause improvement of ozone fastness. The improvement can be determined by comparing the ozone fastness of the ink-jet ink with a control ink-jet ink that does not include the amine additive.

Claims (10)

1. An ink-jet ink composition, comprising:
a metallized phthalocyanine dye; and a liquid vehicle carrying the dye, said liquid vehicle including an amine additive present in the ink-jet ink at an effective concentration to cause improvement of ozone fastness of said ink-jet ink, wherein the improvement is determined by comparing the ozone fastness of the ink-jet ink with a control ink-jet ink that does not include the amine additive.
2. An ink-jet ink as in claim 1, wherein the amine additive is present in the ink-jet ink composition at from 0.01 wt% to 10 wt%, and wherein the metallized phthalocyanine dye is present in the ink-jet ink composition at from 0.01 wt% to 10 wt%.
3. An ink-jet ink as in claim 1, wherein the amine additive is a polyamine.
4. An ink-jet ink as in claim 3, wherein the polyamine is selected from the group consisting of N-methyl-1,3-propanediamine,1,10-phenanthroline, diethylenetriamine, triethylenediamine, N,N-diethylethylenediamine, homopiperazine, piperazine, piperazine-2-carboxylic acid, 1,8-bis-[dimethylamino] naphthalene (proton sponge), N-(2-hydroxyethyl) piperazine-N'-(2 ethane sulfonic acid) (HEPES), 4-(2-hydroxyethyl) piperazine-1-propane sulfonic acid (EPPS), and combinations thereof.
5. An ink-jet ink as in claim 1, wherein the amine additive is a heterocyclic amine additive which does not include oxygen within its ring structure.
6. An ink-jet ink as in claim 1, wherein the amine additive is protonated in the ink-jet ink composition.
7. An ink-jet ink as in claim 1, wherein the metallized phthalocyanine dye is a nickel or copper phthalocyanine dye.
8. An ink-jet ink as in claim 1, wherein the amine additive is molecularly associated with the metallized phthalocyanine dye when the composition is printed onto a substrate.
9. A method for printing images with improved ozone fastness, comprising jetting an ink-jet ink onto a printing medium, said printing medium including an ink-receiving layer coated thereon, said ink-receiving layer comprising semi-metal oxide or metal oxide particulates, said ink-jet ink comprising a metallized phthalocyanine dye, and a liquid vehicle carrying the dye, said liquid vehicle including an amine additive being present in the ink-jet ink at an effective concentration to cause improvement of ozone fastness, wherein the improvement is determined by comparing the ozone fastness of the ink-jet ink with a control ink-jet ink that does not include the amine additive.
10. A method as in claim 9, wherein the amine additive is present in the ink-jet ink composition at from 0.01 wt% to 10 wt%, and wherein the metallized phthalocyanine dye is present in the ink-jet ink composition at from 0.01 wt%
to wt%.
CA2600803A 2005-03-14 2006-03-14 Amine- and phthalocyanine dye-containing ink-jet inks with improved ozone fastness Expired - Fee Related CA2600803C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11/080,209 US7435291B2 (en) 2005-03-14 2005-03-14 Amine- and phthalocyanine dye-containing ink-jet inks with improved ozone fastness
US11/080,209 2005-03-14
PCT/US2006/009423 WO2006099513A1 (en) 2005-03-14 2006-03-14 Amine- and phthalocyanine dye-containing ink-jet inks with improved ozone fastness

Publications (2)

Publication Number Publication Date
CA2600803A1 true CA2600803A1 (en) 2006-09-21
CA2600803C CA2600803C (en) 2011-02-15

Family

ID=36579086

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2600803A Expired - Fee Related CA2600803C (en) 2005-03-14 2006-03-14 Amine- and phthalocyanine dye-containing ink-jet inks with improved ozone fastness

Country Status (11)

Country Link
US (1) US7435291B2 (en)
EP (1) EP1877505B1 (en)
JP (1) JP5199065B2 (en)
CN (1) CN101155885B (en)
AT (1) ATE476481T1 (en)
BR (1) BRPI0608017B1 (en)
CA (1) CA2600803C (en)
DE (1) DE602006015940D1 (en)
RU (1) RU2371462C2 (en)
TW (1) TWI397562B (en)
WO (1) WO2006099513A1 (en)

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JP2006063330A (en) * 2004-07-29 2006-03-09 Canon Inc Inkjet ink, inkjet recording method, ink cartridge, recording unit and inkjet recorder
US20070095250A1 (en) * 2005-10-28 2007-05-03 Uhlir-Tsang Linda C Ink Compositions and Methods for Improving Neutrality, Hue Angle and/or Media Independence
US7811369B2 (en) * 2007-01-31 2010-10-12 Hewlett-Packard Development Company, L.P. Phthalocyanine dyes formulated with salts and anti-flocculent aromatic polyamines for ink-jet imaging
US7641728B2 (en) * 2007-04-23 2010-01-05 Hewlett-Packard Development Company, L.P. Ink composition and method for forming the same
US7897203B2 (en) * 2007-04-23 2011-03-01 Hewlett-Packard Development Company, L.P. Intercalated compound
US20080265211A1 (en) * 2007-04-30 2008-10-30 Rehman Zia Ur Shipping, handling, and testing fluids for ink dispensing systems
JP5125701B2 (en) * 2007-05-07 2013-01-23 コニカミノルタホールディングス株式会社 Inkjet ink
WO2009114684A2 (en) * 2008-03-12 2009-09-17 Sun Chemical Corporation Latex paints with improved fade resistance
US8673272B2 (en) * 2009-07-27 2014-03-18 Isp Investments Inc. Ultraviolet-absorbing compounds
CN104419259A (en) * 2013-09-06 2015-03-18 北京联创佳艺影像新材料技术有限公司 Method for processing dye high in fastness to ozone and application of dye in digital ink jet industry
AR100280A1 (en) * 2014-05-22 2016-09-21 Rohm & Haas POLYMER BINDERS FOR INK JET PRINTERS
US11401429B2 (en) 2016-09-26 2022-08-02 Hewlett-Packard Development Company, L.P. Aqueous ink compositions

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US4155768A (en) * 1977-12-05 1979-05-22 International Business Machines Corporation Waterfast ink for use in ink jet printing
US5026426A (en) * 1989-09-15 1991-06-25 Hewlett-Packard Company Ink compositions having improved waterfastness
US5100470A (en) * 1990-10-25 1992-03-31 Hewlett-Packard Company Waterfast ink formulations for thermal ink-jet using organic amines
US5254159A (en) * 1992-12-17 1993-10-19 Xerox Corporation Ink compositions
GB9322257D0 (en) * 1993-10-28 1993-12-15 Ciba Geigy Ag Pigment composition
JPH11228883A (en) * 1998-02-13 1999-08-24 Seiko Epson Corp Ink and ink jet recording using the same
JPH11323226A (en) * 1998-05-13 1999-11-26 Kao Corp Aqueous ink
US6988794B2 (en) * 2001-03-08 2006-01-24 Matsushita Electric Industrial Co., Ltd. Inkjet recording ink, method for producing said ink, and ink cartridge and recording device having said ink
US6808556B2 (en) 2001-10-29 2004-10-26 Hewlett-Packard Development Company, L.P. Branched alcohols and diols for increased dot size and reliability
EP1308488B1 (en) * 2001-10-30 2007-04-11 Hewlett-Packard Company Ink-jet inks for improved image quality and reliability
US6652085B2 (en) * 2001-10-30 2003-11-25 Hewlett-Packard Development Company, L.P. Enhancement of waterfastness using a polyamine/anionic dye mixture with an acidic fixer
EP1469047B1 (en) * 2002-01-24 2009-04-08 FUJIFILM Corporation Ink for ink-jet recording, ink producing method, and ink-jet recording method
JP3844336B2 (en) * 2002-01-25 2006-11-08 富士写真フイルム株式会社 Ink jet recording ink and ink jet recording method
WO2003066756A1 (en) * 2002-02-08 2003-08-14 Fuji Photo Film Co., Ltd. Ink and ink sets for ink jet printing and method of ink jet printing
JP3849626B2 (en) * 2002-03-13 2006-11-22 ブラザー工業株式会社 Water-based ink for inkjet recording
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JP4072487B2 (en) * 2002-10-02 2008-04-09 キヤノン株式会社 Aqueous ink, ink jet recording method, ink tank, recording unit, and ink jet recording apparatus
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US20070095250A1 (en) * 2005-10-28 2007-05-03 Uhlir-Tsang Linda C Ink Compositions and Methods for Improving Neutrality, Hue Angle and/or Media Independence

Also Published As

Publication number Publication date
RU2007137856A (en) 2009-04-20
US7435291B2 (en) 2008-10-14
ATE476481T1 (en) 2010-08-15
EP1877505A1 (en) 2008-01-16
RU2371462C2 (en) 2009-10-27
TW200641062A (en) 2006-12-01
JP2008536962A (en) 2008-09-11
CN101155885B (en) 2012-05-09
DE602006015940D1 (en) 2010-09-16
US20060201383A1 (en) 2006-09-14
BRPI0608017B1 (en) 2017-04-18
CA2600803C (en) 2011-02-15
BRPI0608017A2 (en) 2009-11-03
CN101155885A (en) 2008-04-02
TWI397562B (en) 2013-06-01
WO2006099513A1 (en) 2006-09-21
JP5199065B2 (en) 2013-05-15
EP1877505B1 (en) 2010-08-04

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