WO2003011983A2 - Compositions d'encre contenant des agents absorbant l'ultraviolet - Google Patents

Compositions d'encre contenant des agents absorbant l'ultraviolet Download PDF

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Publication number
WO2003011983A2
WO2003011983A2 PCT/US2001/024069 US0124069W WO03011983A2 WO 2003011983 A2 WO2003011983 A2 WO 2003011983A2 US 0124069 W US0124069 W US 0124069W WO 03011983 A2 WO03011983 A2 WO 03011983A2
Authority
WO
WIPO (PCT)
Prior art keywords
group
ink
ink composition
lower alkyl
ink jet
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.)
Ceased
Application number
PCT/US2001/024069
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English (en)
Other versions
WO2003011983A3 (fr
Inventor
Ann P. Holloway
James F. Feeman
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.)
Lexmark International Inc
Original Assignee
Lexmark International Inc
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 Lexmark International Inc filed Critical Lexmark International Inc
Priority to PCT/US2001/024069 priority Critical patent/WO2003011983A2/fr
Priority to AU2001279116A priority patent/AU2001279116A1/en
Publication of WO2003011983A2 publication Critical patent/WO2003011983A2/fr
Anticipated expiration legal-status Critical
Publication of WO2003011983A3 publication Critical patent/WO2003011983A3/fr
Ceased legal-status Critical Current

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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
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes

Definitions

  • the present invention relates to ink compositions, and more particularly, to ink compositions comprising ultraviolet absorbers.
  • the ink compositions are particularly suitable for ink jet printing.
  • Inkjet printing is accomplished by ejecting ink from a nozzle toward paper or another print medium.
  • the ink may be driven toward the medium in a variety of ways.
  • electrostatic printing the ink is driven from a nozzle toward a medium by an electrostatic field.
  • squeeze tube Another ink jet printing procedure, known as squeeze tube, employs a piezo-electric element in the ink nozzle. Electrically-caused distortions of the piezo-electric element pump the ink through the nozzle and toward the print medium.
  • thermal or bubble ink jet printing the ink is driven from the nozzle toward the print medium by the formation of an expanding vapor phase bubble in the nozzle.
  • Ink compositions used in ink jet printers generally comprise deionized water, a water-soluble or water-miscible organic solvent, and a colorant.
  • a water-soluble or water-miscible organic solvent generally comprise deionized water, a water-soluble or water-miscible organic solvent, and a colorant.
  • colorant is a soluble dye or pigment.
  • inks comprising soluble dyes or pigments can exhibit many problems, such as poor water-fastness, poor light-fastness,
  • UVAs ultraviolet absorbers
  • an object of the present-invention to provide an ultraviolet absorber that is water-soluble and can be easily and directly added into ink compositions, particularly ink compositions suitable for ink jet printing.
  • the present invention relates to an aqueous ink composition suitable for use in ink jet printers and comprising ink and a water-soluble ultraviolet absorbing compound of the formula
  • R is selected from the group consisting of
  • R 2 is selected from the group consisting of -H and halogen
  • R 3 is selected from the group consisting of -H, halogen, lower alkyl, lower alkoxy, -CO 2 M and -SO 3 M
  • R 7 is selected from the group consisting of -H, -SO 3 M and -NHCO-lower alkyl
  • R g is selected from the group consisting of -H, -CO 2 M and -SO 3 M
  • R ⁇ is selected from the group consisting of -H, -CO 2 M, -SO 3 M and -NHCO-lower alkyl
  • M is selected from the group consisting of -H, -Na, -K, -Li and -N-(R 10 ) 4 wherein each R, 0 is independently selected from the group consisting of -H, lower alkyl and -(CH 2 -CH-O) n -H;
  • R n is selected from the group consisting of -H, -CH 3 and -CH 2 -CH 3 ; and n is from 1 to 4; and wherein the compound contains one or two -SO 3 M groups, one -SO 3 M and one -CO 2 M group, or two -CO 2 M groups.
  • the present invention is directed to an ink jet print cartridge
  • composition comprising ink and a water-soluble ultraviolet absorbing compound of
  • R is selected from the group consisting of
  • R 2 is selected from the group consisting of -H and halogen
  • R 3 is selected from the group consisting of -H, halogen, lower alkyl, lower alkoxy, -CO 2 M and -SO 3 M
  • R 7 is selected from the group consisting of -H, -SO 3 M and -NHCO-lower alkyl
  • R g is selected from the group consisting of -H, -CO 2 M and -SO 3 M
  • R is selected from the
  • each R 10 is independently selected from the group consisting of -H, lower alkyl and
  • R is selected from the group consisting of -H, -CH 3 and -CH 2 -CH 3 ; and n is from 1
  • Another aspect of the present invention comprises an aqueous ink composition comprising ink and a water soluble ultraviolet absorbing compound of the formula
  • R 2 is selected from the group consisting of -H and halogen; R 3 is selected
  • R 4 is selected from the group consisting of halogen, lower alkyl, lower alkoxy, -CO 2 M and -SO 3 M
  • R 4 is selected from the group consisting of halogen, lower alkyl, lower alkoxy, -CO 2 M and -SO 3 M
  • R 5 is selected from the group consisting of -H, halogen, lower alkyl, lower alkoxy, and -OH
  • R ⁇ is selected from the group consisting of -H, halogen, lower alkyl, lower alkoxy, -CO 2 M and -SO 3 M
  • M is selected from the group consisting of -H, -Na, -Li and -N-(R !0 ) 4 wherein each R J0 is individually selected from the group consisting of -H, lower alkyl and -(CH 2 -CH-O) ⁇ -H;
  • R,, R, is selected from the group consisting of -H, -CH 3 and -CH 2 -CH 3 ; and n is from 1 to 4; and wherein the compound contains one or two -SO 3 M groups, one -SO 3 M and one -CO 2 M group or two -CO 2 M groups, with the provision that either (1) R 2 and R 3 are not both hydrogen, or (2) R s is not hydrogen.
  • the ink compositions of the present invention are advantageous in exhibiting good color lightfastness when printed.
  • the compositions are particularly advantageous for use in ink jet printers owing to the easy and direct combination of the aqueous ink and the water soluble ultraviolet absorber.
  • the present invention relates to ink jet ink compositions comprising ink and a
  • R( is selected from the group consisting of
  • R 2 is selected from the group consisting of -H and halogen;
  • R 3 is selected from the
  • R 7 is selected from the group consisting of -H, -SO 3 M and -NHCO-lower alkyl
  • R 8 is selected from the group consisting of -H, -CO 2 M and -SO 3 M
  • Rg is selected from the group consisting of -H, -CO 2 M, -SO 3 M and -NHCO-lower alkyl
  • M is selected from the group consisting of -H, -Na, -K, -Li and -N-(R I0 ) 4 wherein each R 10 is independently selected from the group consisting of -H, lower alkyl and
  • Rn R n is selected from the group consisting of -H, -CH 3 and -CH 2 -CH 3 ; and n is from 1 to 4; and wherein the compound contains one or two -SO 3 M groups, one -SO 3 M and one -CO 2 group, or two -CO 2 M groups.
  • references to lower alkyl throughout this specification refers to C r C g alkyl, preferably C,-C 4 alkyl.
  • reference to lower alkoxy throughout this specification refers to Cj-Cg alkoxy, preferably C,-C 4 alkoxy.
  • R 2 is selected from the group consisting of -H and halogen
  • R 3 is selected from the group consisting of -H, halogen, lower alkyl, lower alkoxy, -CO 2 M and - SO 3 M
  • R 4 is selected from the group consisting of halogen, lower alkyl, lower alkoxy, -CO 2 M and -SO 3 M
  • R 5 is selected from the group consisting of -H, halogen, lower alkyl, lower alkoxy, and -OH
  • R is selected from the group consisting of -H, halogen, lower alkyl, lower alkoxy, -CO 2 M and -SO 3 M
  • M is selected from the group consisting of -H, -Na, -Li and -N-(R 10 ) 4 wherein each R ]0 is individually selected from the group consisting of -H, lower alkyl and -(CH 2 -CH-O) n -H;
  • R M is selected from the group consisting of -H, -CH 3 and -CH 2 -CH 3 ; and n is from 1 to 4; and wherein the compound contains one or two -SO 3 M groups, one -SO 3 M and one -CO 2 M group or two -CO 2 M groups, with the provision that either (1) R 2 and R 3 are not both hydrogen, or (2) R 5 is not hydrogen.
  • Preferred ultraviolet absorbing compounds of the present invention have the following structural formulas
  • the ultraviolet absorbers of the present invention are highly water-soluble, readily dissolve in the usual aqueous vehicles employed in common ink jet compositions, and remain in solution upon extended
  • the ultraviolet absorbing compound is included in the ink compositions in an amount sufficient to improve the light-fastness of printed images.
  • the ink compositions of the present invention comprise from about 0.1 to about 5% by weight of the ultraviolet absorbing compounds. More preferably, the ink compositions
  • the ultraviolet absorbing compounds contain from about 1 to about 3% of the ultraviolet absorbing compounds.
  • .ultraviolet absorbing compounds are preferably used in a salt form, which exhibits satisfactory water solubility.
  • the salt form include sodium, potassium,
  • the ultraviolet absorbent compounds are isolable in the free acid form and convertable to any of the salt forms, or alternatively, may be
  • the ultraviolet absorbing compounds of the present invention may be prepared
  • Suitable ortho-nitro anilines include, for example, 2-nitroaniline, 2- nitroaniline-4-sulfonic acid, 4-amino-3-nitro-benzoic acid, 4-methyl-2-nitroaniline, 4- methoxy-2-nitroaniline, 4-chloro-2-nitroaniline, 5-chloro-2-nitroaniline, 4,5-dichloro- 2-nitroaniline, and 4-ethyl-2-nitroaniline, among others.
  • Suitable phenolic couplers include, for example, 4-hydroxybenzene sulfonic
  • naphthols include, for example, 2-naphthol, 2-na ⁇ hthol-
  • naphthol-6-carboxylic acid l-naphthol-3,6-disulfonic acid, l-naphthol-3 -sulfonic acid, l-naphthol-4-sulfonic acid; l-naphthol-5-sulfonic acid, 2-acetamido-5-hydroxy-
  • naphthalene-7-sulfonic acid 2-acetamido-8-hydroxy-naphthalene-6-suIfonic acid
  • the ink compositions of the present invention are aqueous compositions.
  • water may contain one or more water-miscible solvents, for example in an
  • a suitable carrier mixture depends on the requirements of the specific application involved, such as desired surface tension and viscosity, the selected pigment or dye, the desired drying time of the ink, and the type of paper onto which the ink will be printed.
  • water soluble organic solvents that may be selected include (1) alcohols, such as methyl
  • ketones or ketoalcohols such as acetone, methylethyl ketone and diacetone alcohol
  • ethers such as tetrahydrofuran and dioxane
  • ethers such as
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, triethylene glycol,
  • propylene glycol tetraetheylene glycol
  • polyethylene glycol glycerol, 2-methyl-2,4-
  • Preferred water soluble organic solvents include polyhydric alcohols, such as
  • glycol ethylene glycol, propylene glycol, butylene glycol, triethylene glycol, 1,2,6- hexanetriol, thiodiglycol, hexylene glycol and diethylene glycol; diols, such as butanediol, pentanediol, hexanediol and homologous diols; glycol ethers, such as
  • propylene glycol laureate glycerol
  • polyalkyl glycols such as polyethylene glycol
  • lower alkyl ethers of polyhydric alcohols such as ethylene glycol monomethyl or monoethyl ether, diethylene glycol methyl or ethyl ether, and triethylene glycol monomethyl or monoethyl ether.
  • Particularly preferred organic solvents include ethylene glycol, diethylene glycol, and tetraethylene glycol.
  • ultraviolet absorbing compound as disclosed above, and an aqueous carrier.
  • the key selection criteria for the pigment is that they must be dispersable in the aqueous
  • pigment means an insoluble colorant.
  • pigment particles are sufficiently small to permit free flow of the ink through the ink
  • the jet printing device especially at the ejecting nozzles that usually have a diameter ranging from about 10 microns to about 50 microns.
  • the particle size also has an
  • ink It is also desirable to use small particles for maximum color strength and gloss.
  • the range of useful particle size is from approximately 0.05 micron to approximately
  • the pigment particle size should range from about 0.05 micron to about 5 microns and most preferably, from about 0.05 micron to about 1 micron.
  • Pigments suitable for use in the present invention include, for example, azo
  • pigments such as azo lakes, insoluble azo pigments, condensed azo pigments, and chelate azo pigments, polycyclic pigments, perylene pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, thioindigo pigments,
  • isoindolinone pigments quinophthalone pigments and dry lakes.
  • Additional organic pigments include nitro pigments, nitroso pigments, aniline black and daylight fluorescent pigments.
  • Preferred pigments include titanium oxide, iron oxide, and
  • the present invention include the following: Heliogen® Blue L 690 IF (BASF),
  • Heucophthal® Blue G XBT-583D Heubach
  • Irgalite® Rubine 4 BL Ciba-Geigy
  • the ink compositions may also contain conventional amounts of various modifiers such as binders, surfactants, polymer dispersants, biocides, corrosion
  • inhibitors such as sequestrants, pH buffers, and/or conductivity addivitives. They may also contain further water-soluble ultraviolet light absorbers, if desired.
  • Another embodiment of the present invention comprises an ink jet print cartridge comprising an ink jet ink storage receptacle, an ink jet printhead and an ink jet ink composition comprising ink and a water-soluble ultraviolet absorbing
  • R 2 is selected from the group consisting of -H and halogen
  • R 3 is selected from the group consisting of -H, halogen, lower alkyl, lower alkoxy, -CO 2 M and - SO 3 M
  • R 4 is selected from the group consisting of halogen, lower alkyl, lower alkoxy, -CO 2 M and -SO 3 M
  • R s is selected from the group consisting o -H, halogen, lower alkyl, lower alkoxy, and -OH
  • Rg is selected from the group consisting of -H, halogen, lower alkyl, lower alkoxy, -CO 2 M and -SO 3 M
  • M is selected from the group consisting of -H, -Na, -Li and -N-(R 1D ) 4 wherein each R 10 is individually selected from the group consisting of -H, lower alkyl and -(CH 2 -CH-O) n -H;
  • R n is selected from the group consisting of -H, -CH 3 and -CH 2 -CH 3 ; and n is from 1 to 4; and wherein the compound contains one or two -SO 3 M groups, one -SO 3 M and one -CO 2 M group or two -CO 2 M groups, with the provision that either (1) R 2 and R 3 are not hydrogen, or (2) R 5 is not hydrogen.
  • This example is directed to ink compositions of the present invention which
  • the ink jet ink compositions were formulated using conventional ink jet inks comprising either sodium dye salts or tetramethylammonium (TMA) dye salt.
  • TMA tetramethylammonium
  • yellow ink was formulated employing a tetramethylammonium (TMA) dye salt and 3% of the ultraviolet absorbing compound (V).
  • Magenta and cyan inks were formulated using sodium dye salts and 3% of the ultraviolet absorbing compound (V).
  • Comparative ink jet compositions were formulated using conventional cyan, magneta and yellow inks without incorporating the 3% ultraviolet absorbing compound.
  • the ink jet ink compositions comprising the ultraviolet absorbing compound showed dramatic improvement in light-fastness for most of the ink compositions in various paper types. Furthermore, the most dramatic improvement in light-fastness was demonstrated by the yellow ink containing the 3% ultraviolet absorbing compound.
  • the yellow ink employs a tetramethylammonium (TMA) dye salt as compared to the sodium dye salts used in the magenta and cyan inks.
  • TMA tetramethylammonium
  • ink jet ink compositions were prepared using conventional ink jet inks and 3% of the ultraviolet absorbing compound VIII as shown above. Comparative ink jet ink compositions were formulated comprising the same ink jet inks without the 3% ultraviolet absorbing
  • the yellow ink was prepared using a TMA dye salt while the magenta and cyan inks were prepared using sodium dye salts.
  • Example 1 Similar to Example 1, the ink jet ink compositions of the present invention and the comparative ink jet inks were then used in ink jet printing on the three types of paper as described in Example 1. Light-fastness of the ink jet ink compositions was
  • the ink jet ink compositions of the present invention employing a 3% ultraviolet absorbing compound showed dramatically lower delta E values than the comparative ink jet ink compositions. Therefore, the ink jet ink compositions of the present invention have superior light-fastness as compared to conventional ink jet ink compositions. It can be noted from Table 2 that the most dramatic improvement with the 3% ultraviolet absorbing compound was seen with the yellow ink.
  • Inkjet ink compositions of the present invention which utilize the ultraviolet absorbing compound of Example 2 were formulated. Tetramethylammonium dye salts were employed in making the yellow, magenta and cyan inks. The tetramethylammonium dye salts were mixed with 3% of the ultraviolet absorbing compound to form yellow, magenta and cyan ink jet ink compositions. Comparative ink jet ink compositions were also prepared as detailed in Example 1. The ink jet ink compositions of the present invention and the comparative ink jet ink compositions were then used for ink jet printing to measure light-fastness as described in Example 1. Table 3 details the results of this example.
  • ink jet ink compositions comprising the ultraviolet absorbing compounds of the present invention demonstrate improvements in light- fastness. Moreover, the most dramatic improvement in light-fastness was seen with the ink jet ink compositions comprising tetramethylammonium dye salts and the
  • present invention exhibit surprising results in the improvement of light-fastness over

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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

Compositions d'encre contenant des composés absorbant l'ultraviolet représentés par la formule I, dans laquelle R1, R2, et R3 sont définis dans la demande ; le composé contient un ou deux groupes -SO3M, un groupe -SO3M et un groupe -CO2M, ou deux groupes -CO2M. Compositions d'encre pour jet d'encre contenant des composés absorbant l'ultraviolet représentés par la formule IV, dans laquelle R2, R3, R4, R5 et R6 sont tels que définis dans la demande ; le composé contient un ou deux groupes -SO3M, un groupe -SO3M et un groupe -CO2M, ou deux groupes -CO2M, à condition que : soit (1) R2 et R3 ne représentent pas chacun hydrogène, soit (2) R5 ne représente pas hydrogène. Ces compositions d'encre conviennent pour l'impression à jet d'encre.
PCT/US2001/024069 2001-08-01 2001-08-01 Compositions d'encre contenant des agents absorbant l'ultraviolet Ceased WO2003011983A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/US2001/024069 WO2003011983A2 (fr) 2001-08-01 2001-08-01 Compositions d'encre contenant des agents absorbant l'ultraviolet
AU2001279116A AU2001279116A1 (en) 2001-08-01 2001-08-01 Ink compositions containing ultraviolet absorbers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2001/024069 WO2003011983A2 (fr) 2001-08-01 2001-08-01 Compositions d'encre contenant des agents absorbant l'ultraviolet

Publications (2)

Publication Number Publication Date
WO2003011983A2 true WO2003011983A2 (fr) 2003-02-13
WO2003011983A3 WO2003011983A3 (fr) 2009-06-11

Family

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PCT/US2001/024069 Ceased WO2003011983A2 (fr) 2001-08-01 2001-08-01 Compositions d'encre contenant des agents absorbant l'ultraviolet

Country Status (2)

Country Link
AU (1) AU2001279116A1 (fr)
WO (1) WO2003011983A2 (fr)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4041044A (en) * 1974-11-25 1977-08-09 Ciba-Geigy Corporation Process for the production of 2-aryl-2H-benzotriazoles
EP0415880B1 (fr) * 1989-08-25 1995-04-05 Ciba-Geigy Ag Encres stabilisées à la lumière
ATE127870T1 (de) * 1990-12-13 1995-09-15 Ciba Geigy Ag Wässrige dispersion schwerlöslicher uv-absorber.

Also Published As

Publication number Publication date
AU2001279116A1 (en) 2003-02-17
AU2001279116A8 (en) 2009-07-30
WO2003011983A3 (fr) 2009-06-11

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