Radiation imagery chemistry: process – composition – or product th – Electric or magnetic imagery – e.g. – xerography,... – Radiation-sensitive composition or product
Reexamination Certificate
1995-08-03
2001-01-30
RoDee, Christopher D. (Department: 1753)
Radiation imagery chemistry: process, composition, or product th
Electric or magnetic imagery, e.g., xerography,...
Radiation-sensitive composition or product
C430S078000, C430S124300
Reexamination Certificate
active
06180301
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention is generally directed to hydroxygallium phthalocyanines and photoconductive imaging members thereof, and, more specifically, the present invention is directed to tetrafluoro substituted phthalocyanines, photoconductive imaging members thereof, and processes for the preparation thereof. In embodiments, the processes of the present invention comprise the reaction of fluorophthalonitrile with a gallium halide, preferably a gallium chloride in an organic solvent like N-methylpyrrolidone, a halonaphthalene such as 1-chloronaphthalene, quinoline, and preferably 1-chloronaphthalene, and the like to provide the precursor pigment tetrafluorohalogallium phthalocyanine, and preferably tetrafluorochlorogallium phthalocyanine, subsequently hydrolyzing or acid pasting the aforementioned precursor to preferably provide tetrafluoro hydroxygallium phthalocyanine Type I; and thereafter mixing the Type I in the presence of certain solvents, such as N,N-dimethylformamide, dimethylaminoethanol, isopropanol, and preferably N-methylpyrrolidone to enable a unique polymorphic form of tetrafluoro hydroxygallium phthalocyanine for each solvent that is used, including a very light sensitive Type V tetrafluoro hydroxygallium phthalocyanine. Embodiments of the present invention relate to certain tetrafluoro hydroxygallium phthalocyanines, such as Type I, II, III, IV, and V, processes thereof, and photoconductive imaging members thereof. Moreover, in embodiments the present invention relates to mixtures of tetrafluoro hydroxygallium phthalocyanines and hydroxygallium phthalocyanines, processes thereof, and photoconductive imaging members thereof.
With the present invention, in embodiments there is provided Type V tetrafluoro hydroxygallium phthalocyanine with an X-ray powder diffraction trace having a major peak at Bragg angles of 6.6, and minor peaks at 6.0, 13.4, 14.7, 15.9, 16.9, 26.1, and 27 degrees 2&THgr;; Type I tetrafluoro hydroxygallium phthalocyanine with an X-ray powder diffraction trace having a major peak at Bragg angles of 6.5, and minor peaks at 15.6, and 26.5 degrees 2&THgr;; Type II tetrafluoro hydroxygallium phthalocyanine with an X-ray powder diffraction trace having a major peak at Bragg angles of 6.6, and minor peaks at 12.7, 15.4, 26.3, and 27.0 degrees 2&THgr;; Type III tetrafluoro hydroxygallium phthalocyanine with an X-ray powder diffraction trace having a major peak at Bragg angles of 7.5, and minor peaks at 9.1, 15.6, 16.5, 19.5, 21.8, 22.6, and 27.3 degrees 2&THgr;; and Type IV tetrafluoro hydroxygallium phthalocyanine with an X-ray powder diffraction trace having a major peak at Bragg angles of 6.5, and minor peaks at 7.5, 15.2, 15.7, and 26.5 degrees 2&THgr;.
More specifically, in embodiments the process of the present invention comprises the formation of a precursor prepared by the reaction of 1 weight part, or weight percent gallium chloride with from about 1 weight part to about 10 weight parts, and preferably about 4 weight parts 4-fluorophthalonitrile in a solvent, such as quinoline, chloronaphthalene, or N-methylpyrrolidone, and which solvent is selected in an effective amount such as, for example, from about 5 weight parts to about 100 weight parts and preferably about 15 weight parts, for each part of gallium chloride that is used, to provide a pigment precursor tetrafluoro chlorogallium phthalocyanine, which is subsequently washed with a component, such as dimethylformamide, to provide the precursor tetrafluoro chlorogallium phthalocyanine as determined by X-ray powder diffraction with an X-ray powder diffraction trace having peaks at Bragg angles of 16.5, 25.5, 26.2, 27.3, and 28.8 and the highest peak at 7.0 degrees 2&THgr;; dissolving 1 weight part of the resulting precursor pigment tetrafluoro chlorogallium phthalocyanine in concentrated, about 94 percent, sulfuric acid, which acid is selected in various effective amounts, such as in an amount of from about 1 weight part to about 100 weight parts and in an embodiment about 25 weight parts, by stirring the pigment precursor tetrafluoro chlorogallium phthalocyanine in the acid for an effective period of time, for example from about 30 seconds to about 24 hours, and in an embodiment about 2 hours at a temperature of from about 0° C. to about 25° C., and preferably below about 10° C. in air or under an inert atmosphere, such as argon or nitrogen; adding the resulting mixture in a dropwise manner at a rate of about 0.5 milliliter per minute to about 10 milliliters per minute, and in an embodiment about 1 milliliter per minute to a stirred organic solvent, which can be a mixture comprised of from about 1 volume part to about 10 volume parts and preferably about 4 volume parts of concentrated aqueous ammonia solution (14.8 N) and from about 1 volume part to about 10 volume parts, and preferably about 6 volume parts of water for each volume part of acid like sulfuric acid that was used, which solvent mixture was chilled to a temperature of from about −25° C. to about 10° C. and in an embodiment about −5° C. while being stirred at a rate sufficient to create a vortex extending to the bottom of the flask containing the solvent mixture; isolating the resulting blue pigment by, for example, filtration; and washing the tetrafluoro hydroxygallium phthalocyanine product obtained with deionized water by redispersing and filtering from portions of deionized water, which portions are from about 10 volume parts to about 400 volume parts, and in an embodiment about 200 volume parts for each weight part of precursor pigment tetrafluoro chlorogallium phthalocyanine which was used. The product obtained as a wet cake, approximately 10 percent by weight pigment and 90 percent by weight water, can then be oven dried at a temperature of from about 40° C. to about 100° C. and in an embodiment about 50° C. for a period of from about 12 hours to about 1 week and in an embodiment about 24 hours The product, a dark blue solid, Type I tetrafluoro hydroxygallium phthalocyanine, had an X-ray diffraction pattern having major peaks at 6.9, 13.1, 16.4, 21.0, 26.4, and the highest peak at 6.9 degrees 2&THgr;. The resulting dried intermediate product, Type I tetrafluoro hydroxygallium phthalocyanine, can then be converted to different polymorphic forms by stirring in the presence of a solvent, present in an amount of from about 1 weight part to about 50 weight parts and in an embodiment about 15 weight parts per weight part of Type I tetrafluoro hydroxygallium phthalocyanine that was used, at room temperature, about 25° C., for a period of from about 2 hours to about 2 weeks, and in an embodiment about 1 week. The stirring can be effected with a magnetic stirrer, or in an embodiment by placing said pigment and said solvent in a sealed glass jar containing glass beads, 1 millimeter in diameter, present in an amount of from about 10 weight parts to about 100 weight parts and in an embodiment about 30 weight parts per weight part of Type I tetrafluoro hydroxygallium phthalocyanine that was used, and milling said pigment/solvent mixture on a ball mill. In one invention embodiment, there is used, for example, N,N-dimethylformamide as the solvent, which results in the product, Type II tetrafluoro hydroxygallium phthalocyanine. In another separate embodiment of the present invention, there is used, for example, dimethylaminoethanol as the solvent, which results in the product, Type III tetrafluoro hydroxygallium phthalocyanine. In another separate embodiment there is used, for example, isopropanol as the solvent, which results in the product, Type IV tetrafluoro hydroxygallium phthalocyanine. In another separate embodiment there is used, for example, N-methylpyrrolidone as the solvent, which results in the product, Type V tetrafluoro hydroxygallium phthalocyanine.
Examples of advantages associated with the present invention in embodiments thereof include excellent dispersion quality, as observed by careful visual inspection of the coating of the photogenerating layer containing the pigment Type V tetrafluo
Hsiao Cheng-Kuo
Mayo James D.
Palazzo E. O.
Rodee Christopher D.
Xerox Corporation
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