JPH0129825B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to novel disazo compounds. BACKGROUND ART Inorganic photoreceptors using inorganic photoconductive materials such as selenium, cadmium sulfide, and zinc oxide have been widely used in electrophotography. ``Electrophotography'' generally refers to a method in which a photoconductive photoreceptor is first charged in a dark place by corona discharge, etc., and then subjected to imagewise exposure to selectively discharge the charges in the exposed areas, leaving the unexposed areas free of electrostatic charge. This is one of the image forming methods that leaves an image and further visualizes this latent image using a developing means using toner or the like to form a surface image. The basic characteristics required of the photoreceptor used in such electrophotography are (1) ability to be appropriately charged in the dark, (2) excellent charge retention in the dark, and ability to discharge the charge. (3) high photosensitivity and rapid discharge of charges upon irradiation with light; and excellent mechanical strength and flexibility. Although the conventional inorganic photoreceptors have several advantages, they also have various disadvantages. For example, the selenium photoreceptors currently widely used are (1) to
Although condition (3) is satisfied to a considerable extent, mechanical strength and flexibility are not satisfactory. In particular, as a variety of processes have been adopted in recent electrophotography methods, photoreceptors that are compatible with all of these processes have become required, and for example, flexible shapes are required. However, the selenium photoreceptor has low flexibility and is difficult to produce in such a shape. Similar drawbacks can also be cited for inorganic photoreceptors other than selenium photoreceptors. In recent years, in order to eliminate the drawbacks of these inorganic photoreceptors, organic electrophotographic photoreceptors using various organic photoconductive materials have been researched and developed, and have been put into practical use. For example, poly-N-vinylcarbazole and 2,4,7-trinitrofluorene-9 are coated on a support.
Photoreceptor with a photosensitive layer containing poly-N-vinylcarbazole sensitized with a pyrylium salt dye (Japanese Patent Publication No. 48-25658) (see Japanese Patent Publication No. 37543), a photoreceptor with a photosensitive layer containing a disazo pigment as the main component (see Japanese Patent Application Laid-open No. 1983-37543), and a photoreceptor with a photosensitive layer containing a eutectic complex consisting of a dye and a resin as the main component. Examples include photoreceptors (see Japanese Patent Application Laid-open No. 10735/1983). Although these organic photoreceptors have improved the mechanical properties and flexibility of the inorganic photoreceptors to some extent, they generally have low photosensitivity and do not fully satisfy the requirements for electrophotographic photoreceptors. In general, the characteristics of an electrophotographic photoreceptor are greatly influenced by the materials used, the manufacturing method, etc., but they are particularly dependent on the photoconductive material. For this reason, research into photoconductive materials has been actively conducted, and the present invention also relates to this. An object of the present invention is to provide a novel disazo compound which solves the drawbacks of the conventional photoconductive materials for photoreceptors and which is particularly useful as a photoconductive material. That is, the present invention is based on the general formula [In the formula, A is

[Formula] or

[Formula] (R is selected from the group consisting of a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group, a nitro group, a dimethylamino group, a diethylamino group, and a phenyl group, and n is 1 or (represents an integer of 2)] is a disazo compound represented by In addition, in the general formula and, when n is 2, R may be the same or different. The disazo compound of the present invention represented by the above general formula is a novel compound with colored crystals at room temperature. Specific examples are shown in Table 1 below, along with melting points, elemental analysis values, and infrared absorption spectrum data.

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[Table] To produce the disazo compound of the general formula of the present invention, N,N'-bis(2-hydroxy-3
-Naphthoyl)-4,4'-diaminobibenzyl and a naphthalenediazonium salt or benzenediazonium salt derivative of the general formula are dissolved in an organic solvent such as N,N-dimethylformamide or dimethyl sulfoxide, and the solution is heated at about -10°C to An aqueous alkaline solution such as an aqueous sodium acetate solution may be added dropwise at a temperature of 30°C. The reaction is completed in 5 to 30 minutes, and the desired novel disazo compound of the present invention is obtained. The appropriate amount of the compound of the general formula to be used is about 2 to 5 moles per 1 mole of the compound of the formula. Also, compounds of the formula include, for example, 4,4'-diaminobibenzyl and 2-hydroxy-3-naphthoic acid chloride

[Production of N,N'-bis(2-hydroxy-3-naphthoyl)-4,4'-diaminobibenzyl]

21.2 gr of 4,4-diaminobibenzyl was dissolved in 200 ml of dioxane, while 2-hydroxy-3-
Naphthoic acid chloride 41.3gr dioxane 200ml
Dissolved in pyridine, added the previous solution, and added pyridine.
19gr was added and reacted at 90-95°C for 5 hours. The resulting pale yellow precipitate was collected, washed with water, and then dried. This product was recrystallized from a mixed solvent of N,N-dimethylformamide and water, giving 36.4g of pale yellow crystals (yield:
65.7%). The melting point and elemental analysis values are shown below. Melting point Elemental analysis above 300℃ C H N Calculated value (%) 78.24 5.11 5.07 Actual value (%) 77.93 5.01 5.20 Infrared absorption spectrum (KBr tablet method) is the first
As shown in the figure, absorption bands based on amide groups were observed at 1660 cm ^-1 and 1640 cm ^-1 . Example 2 (Disazo compound: Production of compound No. 1) 1.38 gr of N,N'-bis(2-hydroxy-3-naphthoyl)-4,4'-diaminobibenzyl obtained in Example 1 and benzenediazonium tetra 0.96 gr of fluoroborate was dissolved in 500 ml of cooled N,N-dimethylformamide, and a solution consisting of 0.82 gr of sodium acetate and 10 ml of water was added dropwise thereto over about 5 minutes at room temperature, followed by stirring at room temperature for 3 hours.
Thereafter, the formed precipitate was collected, washed three times with 300 ml of water, and then washed with 300 ml of N,N-dimethylformamide.
Wash 5 times with ml. Reconstitute remaining N, N with acetone.
- Rinse off dimethylformamide and heat to 2mm at 70°C.
Compound No. shown in Table 1 was dried under reduced pressure of Hg.
1.6 g (87%) of disazo compound No. 1 was obtained. The infrared absorption spectrum of the obtained disazo compound is shown in FIG. Examples 3 to 17 (Disazo compound: Compound No. 2 to
16) Compounds No. 2 to 1 shown in Table 1 were prepared in the same manner as in Example 2, except that the compound shown in Table 2 below was used as the diazonium component in the production of the disazo compound of Compound No. 1 in Example 2. Sixteen disazo compounds were prepared.

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【table】 [Brief explanation of drawings]

Figure 1 shows the infrared absorption spectrum of N,N-bis(2-hydroxy-3-naphthoyl)-4,4'-diaminobibenzyl obtained in Example 1.
The figure shows an infrared absorption spectrum of the novel disazo compound of the present invention obtained in Example 2.

Claims (1)

[Claims] 1. General formula [In the formula, A is [Formula] or [Formula] (R consists of a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group, a nitro group, a dimethylamino group, a diethylamino group, and a phenyl group) selected from the group, n represents an integer of 1 or 2)] A disazo compound represented by the following.