Compositions: coating or plastic – Coating or plastic compositions – Marking
Reexamination Certificate
2000-10-12
2002-10-15
Klemanski, Helene (Department: 1755)
Compositions: coating or plastic
Coating or plastic compositions
Marking
C106S031480, C106S031580, C347S100000
Reexamination Certificate
active
06464767
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to an ink jet printing method using a pyrazoleazoindole dye as a colorant in an ink jet composition.
BACKGROUND OF THE INVENTION
Ink jet printing is a non-impact method for producing images by the deposition of ink droplets in a pixel-by-pixel manner to an image-recording element in response to digital signals. There are various methods which may be utilized to control the deposition of ink droplets on the image-recording element to yield the desired image. In one process, known as continuous ink jet, a continuous stream of droplets is charged and deflected in an imagewise manner onto the surface of the image-recording element, while unimaged droplets are caught and returned to an ink sump. In another process, known as drop-on-demand ink jet, individual ink droplets are projected as needed onto the image-recording element to form the desired image. Common methods of controlling the projection of ink droplets in drop-on-demand printing include piezoelectric transducers and thermal bubble formation. Ink jet printers have found broad applications across markets ranging from industrial labeling to short run printing to desktop document and pictorial imaging.
The inks used in the various ink jet printers can be classified as either dye-based or pigment-based. A dye is a colorant, which is dissolved in the carrier medium. A pigment is a colorant that is insoluble in the carrier medium, but is dispersed or suspended in the form of small particles, often stabilized against flocculation and settling by the use of dispersing agents. The carrier medium can be a liquid or a solid at room temperature in both cases. Commonly used carrier media include water, mixtures of water and organic co-solvents and high boiling organic solvents, such as hydrocarbons, esters, ketones, etc.
The choice of a colorant in ink jet systems is critical to image quality. For colors such as cyan, magenta, yellow, green, orange, etc., the peak wavelength (&lgr;-max), the width of the absorption curve and the absence of secondary absorptions are important. The colorant should also have a high degree of light fastness after printing onto the ink-receiving element. For aqueous dye-based inks, the dye needs to be sufficiently soluble in water to prepare a solution that is capable of producing adequate density on the receiving element and stable for extended periods of storage without precipitation. High quality ink jet printing with dye-based inks requires dyes which will provide both bright hue and good light stability. It is difficult to find dyes, particularly yellow dyes, which meet all of these requirements.
Aqueous dye-based inks for high-quality, photo-realistic, ink jet printing require water-soluble dyes with excellent color and high light- and water-fastness. Typically the dyes are chosen from acid, direct and reactive dyestuffs developed for the dyeing of natural fibers such as paper, wool and cotton. Water solubility of these dyes is due to the incorporation of negatively charged substituent groups such as sulfo or carboxy.
U.S. Ser. No. 09/306,121, now U.S. Pat. No. 6,174,356 filed May 6, 1999, discloses water-soluble azoindole dyes for use in ink jet printing including dyes derived from diazotizable heteroaromatic amines. However, there is a problem with some of these dyes in that they do not have sufficient light stability.
U.S. Pat. No. 4,685,934 describes water-soluble pyrazoleazoindole yellow and orange dyes useful for conventional dyeing of synthetic fibers and textiles. However, there is no disclosure in this patent for use of these dyes in ink jet printing.
It is an object of this invention to provide an ink jet printing method using bright, readily water-soluble and light stable azoindole dyes derived from diazotizable heteroaromatic amines useful for aqueous ink jet printing.
SUMMARY OF THE INVENTION
This and other objects are achieved in accordance with this invention which relates to an ink jet printing method, comprising the steps of:
A) providing an ink jet printer that is responsive to digital data signals;
B) loading said printer with an ink jet recording element comprising a support having thereon an image-receptive layer capable of accepting an ink jet image;
C) loading said printer with an ink jet ink composition comprising water, a humectant and a water-soluble pyrazoleazoindole dye; and
D) printing on said ink jet recording element using said ink jet ink in response to said digital data signals.
DETAILED DESCRIPTION OF THE INVENTION
In a preferred embodiment of the invention, the pyrazoleazoindole dyes employed in the invention may be represented by the following structure:
wherein:
R
1
and R
3
each independently represents hydrogen, a substituted or unsubstituted alkyl group of 1-6 carbon atoms, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group of 6-10 carbon atoms, a substituted or unsubstituted heteroaryl group of 5-10 atoms or a polyoxyalkylene group of 2-20 alkylene oxide residues;
R
2
, X and Y each independently represents the groups listed above for R
1
, halogen, cyano, carboxy, acyl, nitro, sulfo, a substituted or unsubstituted alkoxy group of 1-6 carbon atoms, a substituted or unsubstituted aryloxy group of 6-10 carbon atoms, a substituted or unsubstituted alkoxy- or aryloxy-carbonyl group of 1-10 carbon atoms, a polyoxyalkylene group of 2-20 alkylene oxide residues, a ureido group, carbamoyl, a substituted or unsubstituted alkyl-, arylalkyl-, aryl-, diaryl- or dialkyl-carbamoyl group of 1-20 carbon atoms, sulfamoyl, a substituted or unsubstituted alkyl-, arylalkyl-, aryl-, diaryl- or dialkyl-sulfamoyl group of 1-20 carbon atoms, acylamino, sulfonylamino, amino, or a substituted or unsubstituted alkyl-, aralkyl-, aryl-, diaryl- or dialkyl-amino group of 1-20 carbon atoms;
n represents an integer from 1-4; and
Z represents cyano, carboxy, sulfo, alkoxycarbonyl, carbamoyl or a substituted or unsubstituted alkyl-, arylalkyl-, aryl-, diaryl- or dialkyl-carbamoyl group of 1-20 carbon atoms;
with the proviso that the dye must contain at least one group capable of imparting water solubility at a pH of about 4-9.
In a preferred embodiment of the invention, R
1
in the above formula represents hydrogen, methyl or 2-carboxyethyl. In another preferred embodiment, R
2
represents methyl or phenyl. In still another preferred embodiment, X represents hydrogen, sulfo, a substituted 1,3,5-triazinylamino group or an N-alkylphthalamido group. In yet another preferred embodiment, R
3
represents 4-sulfophenyl, 2,5-bis-sulfophenyl, methyl, phenyl, 4-carboxyphenyl or 3-sulfopropyl. In yet another preferred embodiment, Y represents hydrogen. In still yet another preferred embodiment Z represents cyano, carboxy or carbamoyl.
In the above definition, examples of a substituted or unsubstituted alkyl group include methyl, ethyl, isopropyl, hydroxyethyl, 3-sulfopropyl and m-carboxybenzyl. Examples of a substituted or unsubstituted aryl group include phenyl, naphthyl, 3,5-biscarboxyphenyl and 4-sulfophenyl. Examples of a substituted or unsubstituted heteroaryl group include pyridyl, imidazolyl and quinolyl. Examples of halogen include chloro, fluoro, bromo and iodo. Examples of an acyl group include acetyl and 4-sulfobenzoyl. Examples of a substituted or unsubstituted alkoxy group include methoxy, 3-carboxypropoxy and 2-hydroxyethoxy. Examples of a substituted or unsubstituted aryloxy group include phenoxy, 3-carboxyphenoxy and 4-sulfophenoxy. Examples of a substituted or unsubstituted alkoxy- or aryloxy-carbonyl group of 1-10 carbon atoms include methoxycarbonyl, ethoxycarbonyl, 2-methoxyethoxycarbonyl and 3-sulfophenoxycarbonyl. Examples of a substituted or unsubstituted alkyl- aralkyl-, aryl-, diaryl-or dialkyl carbamoyl group include N-methylcarbamoyl, N-methyl-N-4-sulfophenyl-carbamoyl, N,N-bis(4-carboxyphenyl)carbamoyl. Examples of a substituted or unsubstituted alkyl- aralkyl-, aryl-, diaryl-or dialkyl sulfamoyl group include N-methylsulfamoyl, N-methyl-N-phenyl-sulfamoyl, N-(p-sulfophenyl)sulfamoyl and N,N-bi
Carroll-Lee Ann L.
Evans Steven
Pyszczek Ellen M.
Weber Helmut
Cole Harold E.
Eastman Kodak Company
Klemanski Helene
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