Compositions: coating or plastic – Coating or plastic compositions – Marking
Reexamination Certificate
1999-10-08
2002-02-26
Sergent, Rabon (Department: 1711)
Compositions: coating or plastic
Coating or plastic compositions
Marking
C008S647000, C106S031010, C106S031130, C106S031430, C106S031450, C106S031610, C106S031750, C523S161000, C528S049000, C528S073000, C528S291000, C528S288000, C528S341000, C528S347000, C528S349000, C528S362000, C560S024000, C560S025000, C560S026000, C560S032000, C560S033000, C560S115000, C560S157000, C560S158000, C549S321000
Reexamination Certificate
active
06350305
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to selected polymeric furanone magenta colorants and a process for making these colorants. Furthermore, the present invention relates to phase change inks containing these colorants as well as selected resins and waxes that incorporate these colorants therein.
2. Description of the Relevant Art
Phase change inks in digital printing applications (also sometimes called solid inks or hot melt inks) have in the past decade gained significant consumer acceptance as an alternative to more traditional printing systems such as offset printing, flexography printing, gravure printing, letterpress printing and the like. Phase change inks are especially desirable for the peripheral printing devices associated with computer technology, as well as being suitable for use in other printing technologies such as gravure printing applications as referenced in U.S. Pat. No. 5,496,879 and German Patent Publications DE 4205636AL and DE4205713AL assigned to Siegwerk Farbenfabrik Keller, Dr. Rung & Co.
In general, phase change inks are in the solid phase at ambient temperature, but exist in the liquid phase at the elevated operating temperature of an ink jet printing device. At the jet operating temperature, droplets of liquid ink are ejected from the printing device and, when the ink droplets contact the surface of the printing media, they quickly solidify to form a predetermined pattern of solidified ink drops.
They are easy to use and safe. They can be easily loaded into the printer by the user, generally in the form of solid sticks of yellow, magenta, cyan and black ink having a solid consistency similar to children's crayons. Inside the printer, these inks are melted at an elevated temperature in a printhead having a number of orifices, through which the melted ink will be ejected onto the desired substrate such as media like paper or an overhead transparency film. Alternatively, the melted ink may be transferred to a rotating drum and then transferred to the substrate. As the ink cools on the substrate, it re-solidifies into the desired image. This resolidification process, or phase change, is instantaneous and a printed, dry image is thus made upon leaving the printer, which is available immediately to the user.
These phase change inks contain no solvents or diluent that can lead to undesired emissions. In all, the use and specific design of the phase change ink addresses many of the limitations of more traditional ink and printing processes.
Furthermore, because the ink is in cool, solid form at any time when the user can actually come in contact with the ink, and the ink is in a molten state only inside the printer (inaccessible to the user), it is generally safe to use. These inks also have long-term stability for shipping and long storage times.
The phase change inks generally comprise a phase change ink carrier composition, which is combined with at least one compatible phase change ink colorant. The carrier composition has been generally composed of resins, fatty acid amides and resin derived materials. Also, plasticizers, waxes, antioxidants and the like have been added to the carrier composition. Generally the resins used must be water-insoluble and the carrier composition may contain no ingredients that are volatile at the jetting temperatures employed. Also, these carrier ingredients should be chemically stable so as not to lose their chemical identity over time and/or under elevated temperature conditions.
Preferably, a colored phase change ink will be formed by combining the above described ink carrier composition with compatible colorant material, preferably subtractive primary colorants. The subtractive primary colored phase change inks comprise four component dyes, namely, cyan, magenta, yellow and black. U.S. Pat. Nos. 4,889,560 and 5,372,852 teach the preferred subtractive primary colorants employed. Typically these may comprise dyes from the classes of Color Index (C.I.) Solvent Dyes, C.I. Disperse Dyes, modified C.I. Acid and Direct Dyes, as well as a limited number of C.I. Basic Dyes. Also suitable as colorants are appropriate polymeric dyes, such as those described in U.S. Pat. No. 5,621,022 and available from Milliken & Company as Milliken Ink Yellow 869, Milliken Ink Blue 92, Milliken Ink Red 357, Milliken Ink Yellow 1800, Milliken Ink Black 8915-67, uncut Reactant Orange X-38, uncut Reactant Blue X-17, and uncut Reactant Violet X-80 or those described in U.S. Pat. No. 5,231,135.
Colored resin reaction products such as those described in U.S. Pat. No. 5,780,528 issued Jul. 14, 1998, and assigned to the assignee of the present invention, are also suitable colorants.
Polymeric colorants are increasingly being utilized in preparing commercial phase change ink jet inks, as well as potentially for use in other applications, such as gravure printing, and other types of inks and coating applications where coloration is desired. For example, the specific class of polymeric dyes characterized by: (1) an organic chromophore having (2) a polyoxyalkylene substituent and optionally (3) a carboxylic acid or non-reactive derivative thereof covalently bonded to the polyoxyalkylene substituent, as described in U.S. Pat. No. 5,621,022 (Jaeger et al.) possess several advantages; including:
(1) These polymeric dyes are very soluble in the phase change carrier composition and possess high water fastness and high resistance to “bleeding” or weeping of the color from the carrier composition when printed samples are subjected to high temperatures or humidity.
(2) These polymeric dyes are thermally stable in the carrier composition. This is important because the resulting phase change ink compositions may remain molten for weeks at a time in the ink jet printer, or otherwise at elevated temperatures.
(3) These polymeric dyes also act as a plasticizer for the formulation. This enables the formulator to replace at least a portion of the commercial plasticizer that is normally part of the formulations disclosed in the inks of U.S. Pat. Nos. 4,889,560 and 5,372,852.
(4) These polymeric dyes are compatible with each other and with most conventional powdered dyes currently used in phase change ink compositions. Thus, mixtures of inks of different colors do not form a precipitate when mixed together during the printing process. This compatibility also allows for the mixing of these polymeric dyes with powdered dyes of the same primary color into the same ink composition to achieve high color strengths that would not be possible with either dye type by itself.
While phase change ink compositions containing this class of polymeric dye colorants have had good commercial success, it must be noted that non-migrating, lightfast magenta colorants are absent from this class of polymeric dyes. The present invention provides a solution to the need for better non-migrating magenta colorants that possess the other advantages of this class of polymeric dyes.
BRIEF SUMMARY OF THE INVENTION
The present invention is based on the discovery of a new class of oligomeric or polymeric furanone magenta dyes. The dyes are useful in a number of applications, including phase change inks. This new class of furanone magenta dyes can be made by a new and commercially viable synthesis that avoids the use of particularly hazardous starting materials and intermediates.
Therefore, one aspect of the present invention is directed to an oligomeric or polymeric furanone magenta colorant comprising a 3-cyano-4-phenyl-2(5H)-furanone adduct wherein the phenyl radical possesses an oligo or polyoxyalkylene substituent. This 3-cyano-4-(p-polyoxyalkylenephenyl)-2(5H)-furanone moiety, referred to above as the furanone adduct, can be further condensed with a variety of electron rich benzaldehyde moieties to produce magenta colorants.
Another aspect of the present invention is directed to a process for making a polymeric furanone magenta colorant comprising the steps of:
(1) subjecting an alkoxylated acetophenone to a halogenation reaction to form a halogenat
Banning Jeffery H.
King Clifford R.
Byorick Judith L.
Sergent Rabon
Xerox Corporation
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