Process for preparing titanyl phthalocyanine crystal by...

Details Process for preparing titanyl phthalocyanine crystal by... Process for preparing titanyl phthalocyanine crystal by...

1991-03-19

2001-05-15

Harrison, Robert H. (Department: 1619)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C430S079000, C540S143000

Reexamination Certificate

active

06232466

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to a process for preparing a titanyl phthalocyanine crystal useful as a photoconductive material.
BACKGROUND OF THE INVENTION
Phthalocyanine compounds are useful as coatings, printing inks, catalysts or electronic materials. In recent years, they have been extensively studied particularly for their use as electrophotographic photoreceptor materials, optical recording materials and photoelectric conversion materials.
In general, phthalocyanine compounds are known to show several different crystal forms depending on the process of production or the process of treatment. The difference in crystal form is known to have a great influence on their photoelectric conversion characteristics. For example, known crystal forms of copper phthalocyanine compounds include &agr;-, &egr;-, &pgr;-, &khgr;-, &rgr;-, and &dgr;-forms in addition to a stable &bgr;-form. It is known that these crystal forms are capable of interconversion by mechanical strain, a sulfuric acid treatment, an organic solvent treatment, a heat treatment, and the like as described, e.g., in U.S. Pat. Nos. 2,770,629, 3,160,635, 3,708,292, and 3,357,989. Further, a relationship between the crystal form of copper phthalocyanine and electrophotographic sensitivity is described in JP-A-50-38543 (the term “JP-A” as used herein means an “unexamined published Japanese patent application”).
With respect to titanyl phthalocyanine, too, various crystal forms have been proposed, including a stable &bgr;-form as disclosed in JP-A-62-67094, an &agr;-form as disclosed in JP-A-61-217050, and other crystal forms as disclosed in JP-A-63-366, JP-A-63-20365, JP-A-64-17066, and JP-A-1-153757.
However, any of the above-described phthalocyanine compounds proposed to date is still unsatisfactory in photosensitivity and durability when used as a photosensitive material. It has thus been demanded to develop a phthalocyanine compound of new crystal form or a process for easily preparing a phthalocyanine compound of stable crystal form.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a process for preparing a stable titanyl phthalocyanine crystal having high photosensitivity.
As a result of extensive investigations, the inventors have found that a titanyl phthalocyanine crystal having a stable crystal form which exhibits high sensitivity and durability as a photoconductive material can be obtained by subjecting amorphous or quasi-amorphous titanyl phthalocyanine to a simple treatment, and thus reach the present invention.
The present invention relates to a process for preparing a stable titanyl phthalocyanine crystal showing at least one diffraction peak at a Bragg angle (2&thgr;±0.2) of 27.3°, which comprises treating amorphous or quasi-amorphous titanyl phthalocyanine with an alcohol solvent, an aromatic solvent, a mixed solvent of an alcohol solvent and an aromatic solvent, or a mixed solvent of an alcohol solvent and water.
The titanyl phthalocyanine crystal prepared by the process of the present invention is useful as a photoconductive material of an electrophotographic photoreceptor.


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Derwent Abstract C88-030128, New Pthalocyanine Crystal Preparation (Jan. 28, 1988).*
JPA-50-38543, Abstract, Apr. 10, 1975.
JPA-62-67094, Abstract, Mar. 26, 1987.
JPA-63-366, Abstract, Jan. 5, 1988.
JPA-64-17066, Abstract, Jan. 20, 1989.
JPA-1-153757, Abstract, Jun. 15, 1989.
JPA-61-217050, Abstract, Sep. 26, 1986.

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