WO2006047576A1 - Reactive color inks - Google Patents
Reactive color inks Download PDFInfo
- Publication number
- WO2006047576A1 WO2006047576A1 PCT/US2005/038526 US2005038526W WO2006047576A1 WO 2006047576 A1 WO2006047576 A1 WO 2006047576A1 US 2005038526 W US2005038526 W US 2005038526W WO 2006047576 A1 WO2006047576 A1 WO 2006047576A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ink
- fixer
- set forth
- colorant
- dye
- 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
-
- 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
- C09D11/40—Ink-sets specially adapted for multi-colour inkjet printing
-
- 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
- C09D11/54—Inks based on two liquids, one liquid being the ink, the other liquid being a reaction solution, a fixer or a treatment solution for the ink
Definitions
- the present invention relates to reactive color inks.
- a fixer can be used to increase the durability ity of ink jet inks in terms of water fastness, smear and smudge fastness, by precipitating the colorant.
- a typical fixer contains a cationic polymer and/or an acid and/or metal salts.
- Cationic polymers suitable for ink jet application are polyamine (at low pH), quaternized polyamines and polyguanidine.
- the fixer is used to immobilize dyes and to increase durability and can be applied prior to the image is printed (underprinting) or after the image is printed (overpri nting).
- the impact of the fixer on color performance is twofold. Firstly, the formation of fixer-dye complex causes hue shift in many cases.
- fixer-dye interaction determines where the fixer-dye complex resides on media and changes how the colors appear.
- Fig 1. is a bar graph showing Bar OD v Water Drip Transfer mOD for selected dyes/combination of dyes using underprinting (UP) and overprinting (OP).
- Fig. 2 is a bar graph showing Bar OD v Water Drip Transfer mOD for selected dyes/combination of dyes using underprinting (UP) and overprinting .
- Fig. 3 is a bar graph showing Bar OD v Water Drip Transfer mOD for selected dyes/combination of dyes using underprinting and overprinting.
- Fig. 4 is a table summarizing the best gamut (CMY only) achieved using underprinting.
- Fig. 5 is table summarizing the best gamut (CMY only) achieved usi ng overprinting.
- Fig. 6 is a table summarizing the best gamut (CMY only) achieved without using pure dyes which are prone to fail lightfastness tests.
- Figs. 7 - 9 are graphic comparisons which are plotted in terms of Spectral OD and Wavelength for selected dyes with fixer underprinting.
- Fig. 10 is a graph in terms of Absorbance and Wavelength respectively demonstrates UV-Vis solution spectra for various magenta dyes ..
- Fig. 11 is a table which lists the spectral band width of the spectrum at O. ⁇ max and band centers for a plurality of different magenta dyes.
- Fig. 12 is a graph which is expressed in terms of chroma and bandwidth and which compares slow, medium and fast precipitating dyes.
- Fig. 13 compares results for a plurality of dyes/combinations in terms of Transfer OD and Bar OD for Hammermill® and Lustra Laser® papers.
- Fig. 14 shows the results of color gamut calculations using various magenta dyes with cyan and yellow dye blends, wherein the gamut volume is estimated from CMYRGBKW.
- Figs. 15A - 15E and 16A - 16F are micrographs of various magenta dyes in the red area fills.
- the invention is directed to improve color performance by using different dyes and/or and dye mixtures with an ink vehicle.
- the basis of the invention is to use a single slow-precipitating dye or a blend of fast and slow precipitating colorants in order to optimize color space and other attributes (such as lightfastness and pen reliability). That is to say, as noted above, a fixer induces precipitation of the colorants. However, the rate of precipitation is colorant dependent. Slow precipitating colorants increase dot size and thus enable better color to be achieved as compared with fast precipitating colorants. If the slow precipitating dye is deficient in a certain attribute, it is possible to optimize the color space (chroma) by blending a slow precipitating colorant with a fast precipitating one.
- dyes which can be considered for use include a large number of water-soluble acid and direct dyes.
- anionic dyes include Direct Yellow 86, Acid Red 249, Direct Blue 199, Direct Black 168, and Direct Yellow 132; Aminyl Brilliant Red F-B (Sumitomo Chemical Co.); the Duasyn line of "salt-free" dyes available from Hoechst, Direct Black 168, Reactive Black 31 , Direct Yellow 157, Reactive Yellow 37, Acid Yellow 23, Reactive Red 180, Acid Red 52, Direct Blue 199, and Acid Blue 9; mixtures thereof; and the like.
- Tricon Acid Red 52 Tricon Direct Red 227, and Tricon Acid Yellow 17 (Tricon Colors Incorporated), Bernacid Red 2BMN, Pontamine Brilliant Bond Blue A, BASF X-34, Food Black 2, Catodirect Turquoise FBL Supra Cone. (Carolina Color and Chemical), Direct Blue 86, lntrabond Liquid Turquoise GLL (Crompton and Knowles), Reactive Red 4, Reactive Red 56, Levafix Brilliant Red E-4B (Mobay Chemical), Levafix Brilliant Red E-6BA (Mobay Chemical), Acid Red 92, Direct Brill Pink B Ground Crude (Crompton & Knowles), Cartasol Yellow GTF Presscake (Sandoz, Inc.), Tartrazine Extra Cone.
- Magenta A an H-acid type dye in the form of Formula (B) in WO01/59012 with a 2,6-dimethylmorpholine substitution on the triazine ring.
- AR52 - Acid Red 52 Magenta B - an H-acid magenta dye which by way of example has the following formula (wherein Q is a cation):
- Magenta C - a metalized magenta dye having the formula:
- M is H or a monovalent ion, such as Na + , Li + , K + , NH 4 + , and combinations thereof.
- Magenta E a metalized magenta dye in the form of a nickel chelate of [4-hydroxy-3-(1 H-[1 ,2,4,] triazole-3-ylazo)-naphthalene-1 ,5-disulfonic acid] for example.
- Magenta F an H-acid magenta dye in the form of Formula (B) in WO01/59012 with a morpholine substitution on the triazine ring.
- one or more embodiments of the present invention do not exclude optimization of the dye ratio in the mixtures, using a multi-pass printing technique, and trie use of different vehicles.
- the ink was adjusted to pH 7 with NaOH or HNO 3 and trie dye was either 3% of a single dye or 1.5% of each of two dyes.
- An image was printed using a slightly modified HP Business InkJet 2200 printer manufactured by the Hewlett Packard company. Each of the inks was fixed with either under or over printing using one-pass printmode. Underprinting refers to printing the fixer immediately before inks are printed. Overprinting refers to printing fixer after the inks are printed. Modified HP C4811 pens are used to print inks and fixer at 7pl per 600 dpi each. The printe r was operated under heated condition (85°C). Hammermil® and Lustro Laser®* paper were used. The Hamrnermill® paper represents normal plain paper and the Lustro Laser® paper represents a commercially coated glossy paper. For durability, the test was performed 24 hours after the image was printed.
- the media was set a 45-degree angle where about 250 microliters of water was dripped on the bar image.
- OD of the bar image (“bar OD”) and the drip transfer (optical density of non-imaged area just below the dripped imaged area, "drip transfer OD”) were measured.
- Bar OD and “drip transfer OD” are the above measured OD's minus the media OD.
- the purpose of using the fixer is to improve durability of the printed image.
- the drip/smear tests were carried out 24 hours after the samples were printed.
- the bar OD, water drip transfer OD and higher smear transfer OD on both papers were measured.
- AB9 itself shows the highest OD, however, the drip performance is not desirable.
- the PJ485/AB9 mixture shows higher OD and equivalent durability performance compared to PJ485 alone.
- magenta The signal in OD is not as dramatic as in cyan. Most of the dye or dye mixtures show equal or better durability performance than Magenta A except for AR52 (UP and OP) and M377 (OP).
- a list of gamut and % pantone coverage is generated with 3 cyan, 6 magenta and 5 yellow dyes/dye mixtures (90 combinations total) on Hammermil and Lustro Laser.
- the usage of AB9 shows the highest impact on gamut and/or % pantone coverage on both media.
- the highest gamut volume are listed in the tables shown in Figs. 4 and 5.
- AB9 is not suitab Ie to be the only dye in ink jet inks due to its lack of Iightfastness.
- dyes that are not lightfast e.g., AB9 and AY23
- the best set turned out to be PJ485/AB9, Magenta A and DY132/AY23 for UP and OP on both media.
- the gamut volume is listed in the table shown in Fig. 6.
- Significant improvement over control in the gamut volume can be achieved by blending the dyes.
- Figs. 7A-7C represent the comparison of calculated spectral OD's and measured spectral OD's for three green samples with fixer underprinting: PJ485 with DY132, AB9 with AY23 and PJ485/AB9 with DY132. The highest discrepancy between the measurements and calculation appears when pure PJ485 is used. Also shown in Figs. 8A-8C are micrographs of the green samples.
- the PJ485 with DY132 sample shows PJ485 forming discrete solid deposits on a uniform yellow background (top). The size of the deposits becomes smaller when PJ485/AB9 is used and trie background is greener (bottom). In the case of AB9 with AY23 (middle), no solid deposits are discernible. Similar trend is also observed with overprinting green samples (spectral OD shown in Figs. 9A-9C), although the effect is not as dramatic as the underprinting samples.
- the micrographs and the spectral OD data indicate that the addition rule does not hold if the colors do not mix well when printed.
- the micrographs show that the morphology of fixer-dye complex for PJ485 and AB9 are drastically different.
- the difference in the morphology of the fixer-dye> complex on paper could be due to difference in rate of precipitation of fixer-dye complex as determined by a stopflow device.
- PJ485/AB9 helps to create a better green than PJ485 due to interesting ink/fixer kinetics as illustrated in the micrographs.
- magenta dyes and some of their dye blends are evaluated regarding to durability and color performance.
- the various magenta inks are tested in the same manner as what was described earlier.
- UV-Vis solution spectra of various magenta dyes are shown in Fig. 10.
- "Half band width” and "band center” can be used to characterize color of the dyes. These values are listed in the table shown in Fig. 11.
- the half band width is typically associated with chromaticity of the dyes and is defined as the band width of the spectra at half of the maximum absorbance. The smal ler the band width , the higher the chromaticity.
- Band center indicates roughly where the main absorbance is and is related to the hue.
- the "band center” is d efined as the wavelength in the center of the half band.
- Magenta A and ProJet Fast M 2 show similar absorbance and narrower half band width but the chroma of Magenta ⁇ is higher than that for ProJet Fast M 2 on Lustro Laser media with fixer underprinting.
- a second example is Magenta C vs. RR180 and Magenta B. Magenta C shows much higher absorbance than the other two dyes, however, chroma of Magenta C is significantly lower than RR180 and Magenta B on Lustro Laser with fixer underprinting. Examination of the printed area under an optical microscope shows that Magenta A, RR180 and Magenta B printed area is uniform and featureless while ProJet Fast M 2 and Magenta C show discrete solid deposits on Lustro Laser media. More magenta dyes are tested in the same manner and separate them into three categories:
- FIG. 12 A trend is shown in Fig. 12 by plotting the chroma on Lustro Laser vs the half band width. Chroma on Lustro Laser with fixer underprinting can differ as many as 10 units using dye with different precipitating rates. The "slow precipitating" dyes are always in the upper right corner while the “fast precipitating” dyes locate in the lower left corner. The “medium precipitating” dyes sits between the two boundaries. As a result, the "slow-precipitating" dyes are preferred when used with fixer underprinting for improved color performance.
- magenta dye and dye blends can be used to obtain optimal color and lightfastness properties.
- Several dyes and dye blends are tested in the same manner as other magenta dyes mentioned previously. The durability of these dyes and dye blends are shown in Fig. 13. In general, all the magenta dyes perform similarly in the test.
- Micrographs of red area fills created with different magenta dyes on Lustro Laser are shown in Figs. 15A-15E and 16A - 16F. These micrographs shed lights on the kinetics of precipitation of fixer/dye complex.
- Examples of slow-precipitating dyes are AR289, RR180, Magenta F, Magenta A and Magenta D.
- Example of medium-precipitating dye are: ProJet Fast Magenta 2, Magenta B, Magenta C and Magenta E.
- Examples of fast-precipitating dyes are AR94 and DR227.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2005800446581A CN101087856B (en) | 2004-10-25 | 2005-10-25 | Reactive color inks |
BRPI0516895-3A BRPI0516895A (en) | 2004-10-25 | 2005-10-25 | ink for use in inkjet printing, ink system and fixer for use in inkjet printing and printing method |
JP2007539063A JP4825805B2 (en) | 2004-10-25 | 2005-10-25 | Reactive color ink |
EP05821085A EP1833929A1 (en) | 2004-10-25 | 2005-10-25 | Reactive color inks |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US62107904P | 2004-10-25 | 2004-10-25 | |
US60/621,079 | 2004-10-25 | ||
US11/256,177 | 2005-10-24 | ||
US11/256,177 US7951233B2 (en) | 2004-10-25 | 2005-10-24 | Reactive color inks |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006047576A1 true WO2006047576A1 (en) | 2006-05-04 |
Family
ID=36205792
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2005/038526 WO2006047576A1 (en) | 2004-10-25 | 2005-10-25 | Reactive color inks |
Country Status (6)
Country | Link |
---|---|
US (1) | US7951233B2 (en) |
EP (1) | EP1833929A1 (en) |
JP (1) | JP4825805B2 (en) |
CN (1) | CN101087856B (en) |
BR (1) | BRPI0516895A (en) |
WO (1) | WO2006047576A1 (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9090789B2 (en) * | 2006-12-20 | 2015-07-28 | Canon Kabushiki Kaisha | Aqueous ink, ink jet recording method, ink cartridge and ink jet recording apparatus |
CN101896562A (en) * | 2007-12-14 | 2010-11-24 | 惠普发展公司,有限责任合伙企业 | Phosphate-containing surfactants for use with pigment- and latex-containing ink-jet inks |
BR112015016719A2 (en) | 2013-01-14 | 2017-07-11 | 3M Innovative Properties Co | filter, correction or eye protection device, and color discrimination optimization method |
US9012871B2 (en) | 2013-05-02 | 2015-04-21 | Delphax Technologies Inc. | Use of fluorescent inks for document authentication |
CN109627849B (en) * | 2018-11-22 | 2021-09-21 | 武汉纺织大学 | Carbon nanotube/polypyrrole nanotube composite electronic ink and preparation method thereof |
Citations (2)
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EP1077239A1 (en) * | 1999-08-17 | 2001-02-21 | Hewlett-Packard Company | Increasing chroma and edge acuity of dye-based inks by underprinting using vesicle technique |
EP1442889A2 (en) * | 2003-01-28 | 2004-08-04 | Hewlett-Packard Development Company, L.P. | Method of dissolving complexes of anionic dye/cationic polymeric fixer |
Family Cites Families (28)
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US6139139A (en) * | 1992-08-05 | 2000-10-31 | Hewlett-Packard Company | Color inkjet printer with pens containing reactive inks |
US5700314A (en) * | 1994-03-30 | 1997-12-23 | Canon Kabushiki Kaisha | Image forming method, and ink set and ink-jet machinery used therein |
US5549740A (en) * | 1994-07-11 | 1996-08-27 | Canon Kabushiki Kaisha | Liquid composition, ink set and image forming method and apparatus using the composition and ink set |
EP0717089B1 (en) * | 1994-12-12 | 1999-03-24 | Mitsubishi Chemical Corporation | Recording liquid |
US5560766A (en) * | 1995-06-07 | 1996-10-01 | Xerox Corporation | Thermal ink jet composition |
JP4036407B2 (en) * | 1997-12-26 | 2008-01-23 | キヤノン株式会社 | Inkjet printing apparatus and method |
US6120589A (en) | 1998-02-20 | 2000-09-19 | Ricoh Company, Ltd. | Set of color ink compositions for ink-jet printing and method of forming color images using the color ink set |
US5958121A (en) * | 1998-03-24 | 1999-09-28 | Xerox Corporation | Ink compositions and multicolor thermal ink jet printing process for the production of high quality images |
US6299675B1 (en) * | 1998-05-28 | 2001-10-09 | Canon Kabushiki Kaisha | Printing method, image forming process, ink, ink set, recording unit, image forming apparatus and print |
US6228156B1 (en) * | 1998-09-18 | 2001-05-08 | Brother Kogyo Kabushiki Kaisha | Water-based ink for ink jet printing and ink jet printing method |
CA2324125C (en) * | 1999-10-25 | 2007-12-18 | Seiko Epson Corporation | Water-soluble ink composition and ink jet recording apparatus using same |
GB0002902D0 (en) | 2000-02-09 | 2000-03-29 | Avecia Ltd | Compounds |
US6436180B1 (en) * | 2000-03-31 | 2002-08-20 | Hewlett-Packard Company | Color ink composition for graphic art ink jet image printers |
US6630017B2 (en) * | 2000-03-31 | 2003-10-07 | Hewlett-Packard Development Company, L.P. | Inkset for graphic art ink jet image printers |
US6503978B1 (en) * | 2000-05-16 | 2003-01-07 | Hewlett-Packard Company | Enhancement of ink jet image waterfastness with overprinting |
DE10106682A1 (en) * | 2001-02-14 | 2002-08-29 | Clariant Gmbh | Colorant composition |
US6558459B2 (en) * | 2001-02-27 | 2003-05-06 | Hewlett-Packard Development Company | Derivatization of dyes/pigments with crown ethers and inkjet printing fluids containing the same |
US6419353B1 (en) * | 2001-03-02 | 2002-07-16 | Hewlett-Packard Company | Magenta ink formulation |
US6607589B2 (en) * | 2001-04-17 | 2003-08-19 | Hewlett-Packard Development Company, L.P. | Cyan ink formulation |
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DE10260361A1 (en) * | 2001-12-25 | 2003-07-17 | Benq Corp | High-chromaticity magenta inkjet printing ink comprises acid red 92 and at least one other red dye in an aqueous solvent |
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US6673140B2 (en) * | 2002-03-11 | 2004-01-06 | Hewlett-Packard Development Company, L.P. | Ink-jet inks and ink sets providing excellent gamut, image quality, and permanence |
DE60331148D1 (en) | 2002-07-27 | 2010-03-18 | Fujifilm Imaging Colorants Ltd | PROCESS, COMPOSITIONS AND CONNECTIONS |
JP4513255B2 (en) | 2002-12-03 | 2010-07-28 | セイコーエプソン株式会社 | Ink composition for inkjet printing, printing method, and printed fabric |
JP3835408B2 (en) | 2002-12-26 | 2006-10-18 | セイコーエプソン株式会社 | Ink composition for inkjet printing, printing method, and printed fabric |
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-
2005
- 2005-10-24 US US11/256,177 patent/US7951233B2/en not_active Expired - Fee Related
- 2005-10-25 WO PCT/US2005/038526 patent/WO2006047576A1/en active Application Filing
- 2005-10-25 CN CN2005800446581A patent/CN101087856B/en not_active Expired - Fee Related
- 2005-10-25 JP JP2007539063A patent/JP4825805B2/en not_active Expired - Fee Related
- 2005-10-25 EP EP05821085A patent/EP1833929A1/en not_active Withdrawn
- 2005-10-25 BR BRPI0516895-3A patent/BRPI0516895A/en not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1077239A1 (en) * | 1999-08-17 | 2001-02-21 | Hewlett-Packard Company | Increasing chroma and edge acuity of dye-based inks by underprinting using vesicle technique |
EP1442889A2 (en) * | 2003-01-28 | 2004-08-04 | Hewlett-Packard Development Company, L.P. | Method of dissolving complexes of anionic dye/cationic polymeric fixer |
Also Published As
Publication number | Publication date |
---|---|
CN101087856A (en) | 2007-12-12 |
EP1833929A1 (en) | 2007-09-19 |
US7951233B2 (en) | 2011-05-31 |
JP4825805B2 (en) | 2011-11-30 |
BRPI0516895A (en) | 2008-09-23 |
CN101087856B (en) | 2012-09-05 |
JP2008520756A (en) | 2008-06-19 |
US20060087541A1 (en) | 2006-04-27 |
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