WO2006076063A1 - Melanges de colorants noirs trichromatiques, solides a la lumiere, ameliores - Google Patents

Melanges de colorants noirs trichromatiques, solides a la lumiere, ameliores Download PDF

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Publication number
WO2006076063A1
WO2006076063A1 PCT/US2005/038608 US2005038608W WO2006076063A1 WO 2006076063 A1 WO2006076063 A1 WO 2006076063A1 US 2005038608 W US2005038608 W US 2005038608W WO 2006076063 A1 WO2006076063 A1 WO 2006076063A1
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WO
WIPO (PCT)
Prior art keywords
formula
dye
iii
compound
ink
Prior art date
Application number
PCT/US2005/038608
Other languages
English (en)
Inventor
Lawrence M. Krueger
Thomas Sommermann
Original Assignee
Lanxess Corporation
Lanxess Deutschland Gmbh
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 Lanxess Corporation, Lanxess Deutschland Gmbh filed Critical Lanxess Corporation
Priority to TW095100963A priority Critical patent/TW200639219A/zh
Publication of WO2006076063A1 publication Critical patent/WO2006076063A1/fr

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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
    • 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

Definitions

  • the present invention relates to lightfast trichromatic black dye compositions, to inks containing such compositions, and to processes using such inks in printing and imaging technologies, particularly ink jet printing.
  • Lightfastness is a dye property which indicates its resistance to fading due to light exposure.
  • One means of quantifying this property is to measure the change in color of a dye after the dye has been applied to a medium such as paper through the use of inkjet printing and then exposed to light.
  • InkJet printing is a non-impact printing technique which involves ejecting droplets of ink from a fine nozzle directly onto a substrate (paper, textiles, plastic, metal, glass).
  • Inks used in inkjet printers have to meet a variety of criteria, such as good filterability, low salt content, high surface tension, and long-term storage stability, in order to provide printed images which have good optical density, lightfastness, and ozonefastness.
  • various dyes like food black dyes, naphthol direct azo dyes and reactive dyes have widely been known to- date.
  • a typical example of food black dyes includes C.I. Food Black 2, described in JP-A 59-093 766.
  • food dyes give images with poor light fastness. Moderate lightfastness can be achieved using black naphthol direct azo dyes like C.I. Direct Black 168 or C.I. Direct Black 51 , as described in EP-A 0 564 146.
  • Reactive Black 31 are described in EP-A 0 693 537, and give images with high lightfastness.
  • a common disadvantage of using black dyes in an ink jet ink is that a neutral black shade can not easily be obtained. All inks containing black dyes need shading to get a neutral black printout. Furthermore, it is sometimes impossible to obtain the desired shade for special applications with black dyes.
  • trichromatic black compositions of yellow, red and blue dyes are advantageous because almost any shade can be easily adjusted by varying the component ratio.
  • a typical example of a trichromatic composition of yellow and blue stilbene disazo dyes with a red azo dye is described in US-A 4 118 182.
  • the invention relates to a composition
  • a composition comprising a dye mixture containing (1) a dye of Formula I, (2) a dye of Formula II, and (3) a dye of Formula III; where Formula (I) is:
  • R in the above-mentioned formulae is selected from the group consisting of trialkanolammonium, alkyldialkanolammonium, tetraalkylammonium, ammonium, lithium, sodium, potassium, and mixtures thereof.
  • the invention relates to an ink made with such a mixture.
  • the invention relates to a method for dyeing substrates with the above-described mixture.
  • the invention is based on the discovery that by using a certain combination of dyes, it is now possible to make a trichromatic dye composition that exhibits improved lightfastness on a variety of substrates, as compared to certain ordinarily trichromatic dye compositions and certain monochromatic dye compositions.
  • the discovery is unexpected, in part, because of how the unpredictable, synergistic nature of different dye mixtures affect the lightfastness of products containing such dye mixtures.
  • all numbers or expressions referring to quantities of ingredients, reaction conditions, and the like, used in the specification and claims are to be understood as modified in all instances by the term "about.”
  • Various numerical ranges are disclosed in this patent application. Because these ranges are continuous, they include every value between the minimum and maximum values. Unless expressly indicated otherwise, the various numerical ranges specified in this application are approximations.
  • the trichromatic black dye composition of the invention includes a mixture of three dyes having the following formulae: Formula I (C.I. Direct Red 239), Formula Il (C.I. Direct Yellow 133), and Formula III (C.I. Direct Blue 273),
  • R substituents are cations and can be selected from trialkanol- ammonium, alkyldialkanolammonium, tetraalkylammonium, ammonium, lithium, sodium and potassium and combinations thereof.
  • the Direct Red 239 is a known anionic dye and commercially available.
  • the Direct Red 239 is a required component in the mixture that is essential with the Direct Yellow 133 to form the black.
  • the Direct Red 239 has the Formula I
  • R is selected from trialkanolammonium, alkyldialkanolammonium, tetraalkylammonium, ammonium, lithium, sodium, potassium, and mixtures thereof.
  • the Direct Red 239 when used in accordance to the invention, results in a trichromatic black dye composition that imparts improved lightfastness to paper.
  • the Direct Red 239 has a solids content ranging from 1 to 20 or from 1 to 10 weight % solids. In another embodiment, the Direct Red 239 has a solids content containing 12.2wt% color solids.
  • the Direct Yellow 133 is a known anionic dye and commercially available.
  • the Direct Yellow 133 when mixed with the Direct Red 239 and Direct Blue 273 components, forms the black.
  • the Direct Yellow 133 is of the Formula II:
  • R is selected from trialkanolammonium, alkyldialkanolammonium, tetraalkylammonium, ammonium, lithium, sodium, potassium, and mixtures thereof.
  • the Direct Yellow 133 when used in accordance to the invention, results in a trichromatic black dye composition that imparts improved lightfastness to paper.
  • the Direct Yellow 133 has a solids content ranging from 1 to 20 or from 1 to 10 weight % solids. In another embodiment, the Direct Yellow 133 has a solids content containing 11.0 weight % color solids.
  • the Direct Blue 273 is a known anionic dye and commercially available. Without being bound by theory, it is believed that the Direct Blue 273 gives the good lightfastness and adds depth of color. Generally, the Direct Blue 273 is of the Formula III:
  • R is selected from trialkanolammonium, alkyldialkanol- ammonium, tetraalkylammonium, ammonium, lithium, sodium, potassium, and mixtures thereof.
  • the Direct Blue 273 when used in accordance to the invention, results in a trichromatic black dye composition that imparts improved lightfastness to paper.
  • the Direct Blue 273 has a solids content ranging from 1 to 20 or from 1 to 10 weight % solids. In another embodiment, the Direct Blue 273 has a solids content containing 11 weight % color solids.
  • the aqueous dye mixture contains dye components in sufficient amounts such that when the dye mixture is used in an ink to print paper, the dye on the paper exhibits improved lightfastness.
  • the aqueous dye mixture contains from 1.0 to 10.0 weight %, or from 3.0 to 5.0 weight % of Formula (I), from 1.0 to 15.0 weight %, or from 5.0 to 7.0 weight % of Formula (II), and from 10 to 50 weight %, or from 15 to 25 weight % of Formula (III) with the remainder as water. This mixture is the dye concentrate which is then used as the colorant in the ink formulation.
  • Solvents which are miscible with water, can be used with the aqueous dye mixture of the invention. These can be alcohols and their ethers or esters, carbonamides, ureas, sulfoxides and sulfones; particularly those with molecular weight ⁇ 200 g/mole. Examples of those solvents that are particularly suitable for use are: methanol, ethanol, propanol; ethylene-, propylene-, diethylene-, thiodiethylene-, and dipropyieneglycol; butanediol; 2-hydroxypropionitrile, _ .
  • the trichromatic black dye mixture is generally made by blending appropriate amounts of dyes having Formula (I), Formula (II), and Formula (III) in sufficient amounts under conditions that produce a trichromatic dye composition, which when used to print paper, produces printing with improved or comparable lightfastness, as compared to naphthol direct azo dyes like C.I. Direct Black 168, Direct Black 195, or reactive dyes such as C.I. Reactive Black 31.
  • the conditions at which the dyes of Formula (I), Formula (II) and Formula (III) are blended vary, depending on factors such as available equipment, product requirements, and the like. Below are illustrative conditions.
  • the pH of the blend can vary, depending on application. In one embodiment, the pH is 7, and in another embodiment, the pH ranges from 7 to 8.
  • the pH of the trichromatic black dye mixture from the invention can be from 8 to 10, and preferably from 9 to 10. Separation and purification methods can be used in making the trichromatic black dye composition.
  • three purification methods that can be used include: (1) ultrafiltration using a specified membrane to maximize removal of inorganic salts and minimize loss of color, (2) treatment with activated carbon to remove small amounts of surface active agents that negatively affect ink performance, and (3) sub- micron filtration to remove trace amounts of undissolved solids that affect the performance of the ink.
  • an aqueous mixture of the three dyes described in Formulas (I), (II), and (III) can be formed from either powders, liquids, or mixtures thereof, of the three colorants. This mixture is then purified by reverse osmosis or ultrafiltration using an appropriate membrane to remove undesirable inorganic salts such as sodium- or potassium chloride or sodium- or potassium sulfate.
  • the salt content remaining in the purified liquid is normally less than 2 weight %, or less than 1 weight %, or less than 0.2 weight %, based upon the dye mixture.
  • the desalinated liquid is then treated with activated carbon to remove surface active impurities, and subsequently filtered through sub- micron filters to remove small amounts of undissolved material.
  • the trichromatic dye mixture containing (1) a dye of Formula I, (2) a dye of Formula II, and (3) a dye of Formula III of the invention can be used as a component to make an ink that is useful in inkjet systems.
  • the invention provides an ink formulation that includes the following components:
  • composition comprising a trichromatic black dye mixture containing (1) a dye of Formula I, (2) a dye of Formula II, and (3) a dye of Formula III; where Formula (I) is:
  • R in the above-mentioned formulae is selected from the group consisting of trialkanolammonium, alkyldialkanolammonium, tetraalkylammonium, ammonium, lithium, sodium, potassium, and mixtures thereof.
  • a specific ink formulation can include trichromatic dye mixture containing (1) a dye of Formula I, (2) a dye of Formula II, and (3) a dye of Formula III and the other components: water, diethylene glycol monobutyl ether, diethylene glycol, glycerine, an acetylene glycol surfactant, triethanolamine, 2-pyrrolidone, EDTA, and a biocide.
  • Another specific ink formulation can include the following components in addition to the trichromatic black dye composition of the invention: water, ethylene glycol, glycerol, urea, an acetylene glycol ethylene oxide adduct surfactant, and a silicon-containing surfactant.
  • Another specific ink formulation includes the following components in addition to the trichromatic dye mixture containing (1) a dye of Formula I, (2) a dye of Formula II, and (3) a dye of Formula III: water, trimethylolpropane, 2-pyrrolidone, 1,5-pentanediol, a nonionic surfactant, an anionic surfactant, buffer, and EDTA.
  • Dyestuffs can be added in addition to these formulations.
  • the invention provides the following ink formulation:
  • Buffering Agent 0.1 - 0.5 pH control, dye stabilizer
  • UV Absorbers UV Absorbers, Antioxidant light stability, storage stability
  • inks in accordance to the invention can contain the following components in addition to the trichromatic black dye mixture containing (1) a dye of Formula I, (2) a dye of Formula II, and (3) a dye of Formula III: Water 39.6%
  • the trichromatic black dye mixture containing (1) a dye of Formula I, (2) a dye of Formula II, and (3) a dye of Formula III of the invention can be added to the above-mentioned formulations in various amounts, depending on the application. Generally, the amount can range from 1 to 5 wt% or 10wt%. Percentages listed above are in weight %.
  • Suitable solvents that can be used to make inks suitable for inkjet systems include alcohols and their ethers or esters, carbonamides, ureas, sulfoxides and sulfones; particularly those with molecular weight ⁇ 200 g/mole.
  • solvents examples include: methanol, ethanol, propanol; ethylene-, propylene-, diethylene-, thiodiethylene-, and dipropyleneglycol; butanediol; 2-hydroxypropionitrile, pentamethyleneglycol, ethyleneglycolmonoethyl-, propyl- and butylether, ethylenediglycolmonoethylether, triethyleneglycoimonobutylether, butylpolyglycol, formamide, triethyleneglycol, 1 ,5-pentanediol, 1 ,3,6- hexanetriol, acetic acid-2-hydroxyethylester, acetic acid-2(2"-hydroxy)- ethylester, glycerin, glycolacetate, 1 ,2-dihydroxypropane, 1-methyoxy-2- propanol, 2-methoxy-i-propanol, N,N-di
  • Suitable surfactants include nonionic surfactants having an HLB that is more than 5, e.g. 8 or 13.
  • suitable surfactants include SurfynolTM 440, and SurfynolTM 465, available from Air products.
  • Other suitable non-ionic surfactants will be apparent and known to one of ordinary skill in the art.
  • anionic surfactants can be used, depending on the application.
  • the water content of an ink of the invention can vary, depending on the application. Generally, the water content of the ink can range from 50 to 75 wt% or 90wt%. Percentages listed above are in weight %.
  • the ink of the invention can also include other components such as biocides.
  • suitable biocides include and are not limited to imidacloprid, tebuconazole, 1,2-benzisothiazolin-3- one, a mixture of benzylhemiformal and 2-octyl-2H-isothiazol-3-one, a mixture of 2-methyl-4-isothiazolin-3-one and 5-chloro-2-methyl-4- isothiazolin-3-one, and 2,6-dimethyl-/77-dioxan-4 ol acetate.
  • Imidacloprid, tebuconazole, 1 ,2-benzisothiazolin-3-one, a mixture of benzylhemiformal and 2-octyl-2H-isothiazol-3-one, and a mixture of 2-methyl-4-isothiazolin- 3-one and 5-chloro-2-methyl-4-isothiazolin-3-one may be obtained from LANXESS Corporation, Pittsburgh, PA. 2,6-dimethyl-/7?-dioxan-4 ol acetate can be obtained from Dow Chemical under the mark BIOBAN TM DXN
  • An ink of the invention is made by formulating the trichromatic dye mixture containing (1 ) a dye of Formula I, (2) a dye of Formula II, and (3) a dye of Formula III and blending the trichromatic dye mixture with the suitable components.
  • the invention provides an ink cartridge that includes an ink container portion that contains the trichromatic black dye mixture containing (1) a dye of Formula I, (2) a dye of Formula II, and (3) a dye of Formula III.
  • the invention provides an ink set that includes the following components:
  • a cyan ink component (d) and a black ink containing the trichromatic black dye mixture containing (1) a dye of Formula I, (2) a dye of Formula II, and (3) a dye of Formula III.
  • such an ink set will include a combination of a first dye ink having a color tone, and a second dye ink having a color tone different from that of the first dye ink, such that at least one of the first and second dye inks in the ink set contains an ink of the trichromatic black dye mixture containing (1) a dye of Formula I, (2) a dye of Formula II, and (3) a dye of Formula III.
  • the trichromatic dye mixture containing (1 ) a dye of Formula
  • a dye of Formula II can be used to color a variety of substrates.
  • Useful substrates include paper substrates, glass substrates, metal substrates, plastic substrates, and textile substrates.
  • a paper colored with this dye when exposed to light would exhibit a DE value.
  • the magnitude of this DE (a measure of the lightfastness which is the dye's resistance to fading on paper or other media) that is observed depends on the substrate that is being used.
  • the ink is applied to an appropriate medium by using drop-on demand ink jet technology (Thermal inkjet, Bubble-Jet, Piezo inkjet), to develop the letter character or graphic desired.
  • the invention provides previously unavailable advantages.
  • the resulting jet-black dye which, when applied to varying media such as paper, glass, metal, plastic, and textiles, exhibits excellent lightfastness properties and acceptable ozone fastness.
  • Inks of the invention also provide excellent lightfastness and acceptable ozone fastness.
  • the formulated ink was added to a Hewlett-Packard HP 51645 black cartridge and applied to the following media: TCF Special Copy Paper (80 g/m 2 ), HP Bright White InkJet Paper, HP Premium Paper, HP Premium High-Gloss Film Paper. The prints were dried, exposed to light at 290 nm (Atlas Suntest) and at 320 nm (Atlas Alpha) for 12 and 24 hrs.
  • the formulated ink was added to a Hewlett-Packard HP 51645a black cartridge and applied to the following media: TCF Special Copy Paper (80 g/m 2 ), HP Bright White InkJet Paper, HP Premium Paper, HP Premium High-Gloss Film Paper. The prints were dried, exposed to light at 290 nm (Atlas Suntest) and at 320 nm (Atlas Alpha) for 12 and 24 hrs.
  • a desalinated, carbon-treated and 0.2 micron filtered solution of C.I. Direct Black 168 was prepared as described in Example 1. The total dye content in this solution was 25 weight % with an E 1 i value of 75.
  • the formulated ink was added to a Hewlett-Packard HP51645a black cartridge and applied to the following media: TCF Special Copy Paper (80 g/m 2 ), HP Bright White InkJet Paper, HP Premium Paper, HP Premium High-Gloss Film Paper.
  • the prints were dried, exposed to light at 290 nm (Atlas Suntest) and at 320 nm (Atlas Alpha) for 12 and 24 hrs.
  • a desalinated, carbon-treated and 0.2 micron filtered solution of C.I. Reactive Black 31 was prepared as described in example 1.
  • the total dye content in this solution was 13 weight % with an E ⁇ value of 40.
  • the formulated ink was added to a Hewlett-Packard HP51645a black cartridge and applied to the following media: TCF Special Copy Paper (80 g/m 2 ), HP Bright White InkJet Paper, HP Premium Paper, HP Premium High-Gloss Film Paper. The prints were dried, exposed to light at 290 nm (Atlas Suntest) and at 320 nm (Atlas Alpha) for 12 and 24 hrs.

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  • 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)

Abstract

L'invention concerne une composition comprenant un mélange de colorants trichromatique contenant un constituant C.I. rouge direct 239, un constituant C.I. jaune direct 133, ainsi qu'un constituant C.I. bleu direct 273. L'invention concerne également des encres préparées à l'aide du mélange susmentionné, ainsi que des procédés de préparation et d'utilisation du mélange.
PCT/US2005/038608 2005-01-10 2005-10-27 Melanges de colorants noirs trichromatiques, solides a la lumiere, ameliores WO2006076063A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
TW095100963A TW200639219A (en) 2005-01-10 2006-01-10 Improved lightfast, trichromatic black dye mixtures

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US64259605P 2005-01-10 2005-01-10
US60/642,596 2005-01-10

Publications (1)

Publication Number Publication Date
WO2006076063A1 true WO2006076063A1 (fr) 2006-07-20

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PCT/US2005/038608 WO2006076063A1 (fr) 2005-01-10 2005-10-27 Melanges de colorants noirs trichromatiques, solides a la lumiere, ameliores
PCT/US2006/000824 WO2006076365A1 (fr) 2005-01-10 2006-01-10 Melange de colorant noir trichromatique, stable a la lumiere ameliore

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Application Number Title Priority Date Filing Date
PCT/US2006/000824 WO2006076365A1 (fr) 2005-01-10 2006-01-10 Melange de colorant noir trichromatique, stable a la lumiere ameliore

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WO (2) WO2006076063A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102924973A (zh) * 2012-10-25 2013-02-13 上海贝通色彩科技有限公司 一种水性双偶氮染料混合物及其制备方法、用途
TWI487749B (zh) * 2011-05-30 2015-06-11 Nippon Kayaku Kk 染料系偏光元件及偏光板

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4118182A (en) * 1975-11-03 1978-10-03 E. I. Du Pont De Nemours And Company Solutions of azo dyes derived from 4-4-diamino-2,2-stilbenedisulfonic acid
US6641257B1 (en) * 1998-05-29 2003-11-04 American Ink Jet Corporation Lightfast ink jet inks

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4118182A (en) * 1975-11-03 1978-10-03 E. I. Du Pont De Nemours And Company Solutions of azo dyes derived from 4-4-diamino-2,2-stilbenedisulfonic acid
US6641257B1 (en) * 1998-05-29 2003-11-04 American Ink Jet Corporation Lightfast ink jet inks

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI487749B (zh) * 2011-05-30 2015-06-11 Nippon Kayaku Kk 染料系偏光元件及偏光板
CN102924973A (zh) * 2012-10-25 2013-02-13 上海贝通色彩科技有限公司 一种水性双偶氮染料混合物及其制备方法、用途

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Publication number Publication date
WO2006076365A1 (fr) 2006-07-20
TW200639219A (en) 2006-11-16

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