JPS6014781B2 - Novel disazo compound and its production method - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel disazo compound and a method for producing the same.

It has been known that some organic compounds, such as indigo compounds and phthalocyanine compounds, are useful as photoconductive materials for photoreceptors used in electrophotography.

The "electrophotographic method" referred to here generally means that a photoconductive photoreceptor is first charged with a corona discharge, etc., and then exposed to image light to selectively discharge the charges only in the exposed areas, thereby reducing the electrostatic charge. This is one of the image forming methods in which a port image is obtained and the latent image portion is visualized using a developing means using toner or the like to form an image. The basic characteristics required of a photoreceptor in such an electrophotographic method are as follows:
Examples include being charged to an appropriate potential in a dark place, having little charge discharge in a '21 dark place, and quickly discharging a charge by {3} light irradiation. However, the reality is that conventional photoconductive organic compounds do not necessarily fully satisfy these requirements. On the other hand, selenium and zinc oxide are known as photoconductive inorganic materials, and it is a fact that selenium is widely used in practical applications.

However, as various processes have been adopted in recent electrophotographic methods, a photoreceptor that is compatible with all of these processes has become required. In addition to the above-mentioned basic characteristics, there is a growing demand for belt-shaped photoreceptors that have flexibility in shape, for example. However, in the case of selenium, it is generally difficult to form it into such a shape. An object of the present invention is to provide a novel disazo compound which is particularly useful as a photoconductive material and which eliminates the above-mentioned drawbacks of photoconductive materials for photoreceptors, and a method for producing the same. That is, one aspect of the present invention is a general formula [where A is or (where R is a lower alkyl group, a lower alkoxy group, a nitro group, a lower dialkylamino group, or a halogen, and n is 0,1
, 2 or 3, and when n is an integer of 2 or 3, R may be the same or different groups.

). ] This is a novel disazo compound.

This novel disazo compound is a colored crystalline substance at room temperature, and specific examples thereof are as follows.

Among these disazo compounds, Compound No. Infrared absorption spectrum of [1] (KB Kameyodo method)
is shown in Figure 3.

These disazo compounds can be produced by the following methods. That is, another aspect of the present invention is, for example, 9
, 10-bis(4-nitrostyryl)anthracene, which is obtained by reducing the 9,10-bis(4-aminostyryl)anthracene represented by the formula, is diazotized to form a tetrazonium salt represented by the formula (where X represents an anionic functional group). , this can be expressed as general formula (a)
b) or [provided that R is a lower alkyl group, a lower alkoxy group, a nitro group, a lower dialkylamino group, or a halogen, and n is an integer of 0, 1, 2 or 3; When n is an integer of 2 or 3, R may be the same or different groups.

This is a method for producing the above-mentioned novel disazo compound, which is characterized by reacting with a compound represented by the above. The 9,10-bis(4-aminostyryl)anthracene used here is a new compound, such as 9,10-bis(4-nitrostyryl)anthracene represented by the formula (this compound is described, for example, in JP-A-51-98261). obtained by the method described above).

This reduction is carried out in an organic solvent such as N,N-dimethylformamide in the presence of a reducing agent such as iron-hydrochloric acid, which is commonly used for the reduction of nitro groups, at a temperature of 7 to 11,000 psi for about 30 minutes to
This is achieved by reacting for 2 hours. The 9,10 bis(4-aminostyryl)anthracene thus obtained is then diazotized by diazotizing it with an aqueous solution of sodium nitrite in a dilute inorganic acid such as dilute hydrochloric acid or dilute sulfuric acid.
This is done by adding at 10°C.

This diazotization reaction is completed in 30 minutes to 3 hours. Furthermore, it is desirable to add, for example, shelf-hydrofluoric acid to the reaction mixture to precipitate it as a tetrazonium salt, followed by filtration to obtain crystals. This tetrazonium salt is also a new compound. Next, the compound (a' or b) (coupler) is added to this tetrazonium salt to cause a coupling reaction between the tetrazonium salt and the coupling component.

In practice, this reaction involves mixing and dissolving the tetrazonium salt and the coupling component in an organic solvent such as N,N-dimethylformamide, and then dropping an alkaline aqueous solution such as a sodium acetate aqueous solution at a temperature of about 1100 to 1000 °C. This is done by This reaction is completed in 5 minutes to 3 hours. The disazo compound of the present invention is useful as a photoconductive material for electrophotographic photoreceptors. Therefore, for example, [1-disazo compound can be used as polyester, polyamide,
Photoreceptor system of '1' above, in which a layer of fine particles with a diameter of approximately 0.05 to 5 r is provided on a conductive support in a suitable resin such as polyurethane, polyketone, polycarbonate, polystyrene, polyvinyltoluene, etc. and further added an inorganic photoconductive material (for example, known cadmium sulfide, cadmium sulfide-selenium alloy, etc.) or an organic photoconductive material (for example, known polyN-vinylcarbazole, polyvinylpyrene, etc.). A laminated type photoreceptor, etc., in which a thin layer of a disazo compound of about 0.05 to 10 layers is formed on a transparent support by an appropriate method, and another photoconductive substance is further formed on the thin layer, This can be mentioned as an example of the use of the new disazo compound.

The photoreceptor produced in this manner is no inferior to conventional products and can fully achieve the object of the present invention.
Next, the effects of the novel disazo compound of the present invention will be explained using an example of its use in a photoreceptor.

1 part by weight of polyester resin (manufactured by DuPont, Polyester Adhesive 49000), No. 1 part by weight of the disazo pigment No. 1 and 2 parts by weight of tetrahydrofuran are pulverized and mixed in a ball mill, the resulting dispersion is applied onto an aluminum-deposited polyester film using a doctor blade, and dried at 10,000 for 10 minutes to obtain a thickness. A photoreceptor having a photosensitive layer of 7 layers was obtained.

Next, the surface of the photosensitive layer of this photoreceptor was positively charged by performing a Juro V corona discharge using a commercially available electrostatic copying paper tester, and then left at the 2nd stage and 8th stage. Surface potential Vp.

(volts), then from a tungsten lamp,
The photosensitive layer is irradiated with light such that the surface illuminance is 20 lux, and the surface potential is Vp. Find the time (seconds) until it becomes 1'2, and calculate the half-reduced exposure amount EI/2 (lux seconds) (
photosensitivity). The result is Vp. =810V,EI/
2=8.3 lux·sec, showing high light sensitivity. The details of the present invention will be illustrated below with reference to Examples. Example 1 (Production of 9,10-bis(4-aminostyryl)anthracene) 6.0 g of 9,10-bis(p-nitrostyryl)anthracene, 12.0 g of iron powder. Mix 200 g of N,N-dimethylformamide, add dilute hydrochloric acid prepared from 5 parts of concentrated hydrochloric acid and 17 parts of water, and react at 90 to 10,000 for 1 hour with strong shaking.

After the reaction is complete, add 5% aqueous sodium carbonate solution while hot.
Adjust the pH of the reaction mixture to 8. After removing the insoluble matter in a hot furnace, the furnace solution is diluted with 70% water to obtain yellowish brown crystals. The crystals were collected in a furnace, washed with water, and dried to give 9,10-bis(p-aminostyryl)anthracene 5.
．． A female (96.2% yield) is obtained. Melting point 281.5-2.
0qo (decomposition) elemental analysis (as C3 mountain 24N2) Calculated value Actual value C% 87.34 87.
10H% 5.87 5.
79N% 6.79 6.
80 infrared absorption spectrum (KB fin detergent method) and NH
3300-3500 Skin-1 The infrared absorption spectrum of this product is shown in FIG.

Example 2 (Production of disazo compound M.1) 9,10-(p-aminostyryl) obtained in Example 1
Anthracene6. The crabs were added to dilute hydrochloric acid prepared from 50 parts of concentrated hydrochloric acid and 50 parts of water, and the mixture was thoroughly floated for 3 minutes at 60°C, and then the mixture was cooled to about 0°C.

A solution of sodium nitrite dissolved in 2.1 ml and 6 ml of sodium nitrite was added dropwise to this at 0 to 5° C. over about 30 minutes. After that, the mixture was incubated at the same temperature for about 3 seconds, a small amount of unreacted material was removed by the furnace, the furnace solution was poured into 20% of 42% borohydrofluoric acid, and the precipitated crystals were taken out by the furnace. After washing with water and drying, 87 g of red crystals of tetrazonium difluoroborate (yield: 94.
6%). Decomposition point is about 160oo. Infrared absorption spectrum (KB stagnation method) N2
2250 Skin-1 The infrared absorption spectrum of this product is shown in Figure 2.

Next, this tetrazonium salt 4. 2-hydroxy-3-naphthoic acid anilide as a coupler and a coupler is dissolved in 600 mL of cooled N,N-dimethylformamide,
Add 7.0% sodium acetate to this. A solution consisting of 100 parts of water and water was added dropwise at a temperature of 4 to 8°C for 1 hour, and then incubated at room temperature for about 3 hours. Thereafter, the obtained precipitate was taken out of the oven and washed three times with 600 ml of water, and then 8 times with 600 ml of N,N-dimethylformamide. Further remaining N,N
-Dimethylformamide was washed away with acetone, and the obtained blue-black crystals were dried at 70°C under a reduced pressure of 2 phantom Hg to obtain compound No. 1 disazo compound6. (yield 91.2
%). Examples 3 to 15 (Production of disazo compounds 0 to Disazo compounds of RO to XW were produced.

[Brief explanation of drawings]

Figures 1 and 2 are infrared absorption spectra of 9,10 bis-(4-aminostyryl)anthracene and its tetrazonium difluoroborate, which are intermediates for producing the disazo compound of the present invention, and Figure 3 is the infrared absorption spectrum of the present invention. Disazo compound No. according to the invention This is the infrared absorption spectrum of No. 1. Figure 1 Figure 2 Figure 3

Claims (1)

[Scope of Claims] 1. General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [However, A is ▲ There are ▲ mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (However, R is lower alkyl group, lower alkoxy group, nitro group, lower dialkylamino group or halogen, n is 0,
is an integer of 1, 2 or 3, and when n is an integer of 2 or 3, R may be the same or different groups. ). ] A disazo compound represented by 2 The tetrazonium salt represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, X represents an anionic functional group) General formula (a) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or (b) ▲Mathematical formula, There are chemical formulas, tables, etc.▼ (However, in (a) and (b), R is a lower alkyl group, lower alkoxy group, nitro group, lower dialkylamino group, or halogen, and n is an integer of 0, 1, 2, or 3. can be,
When n is an integer of 2 or 3, R may be the same or different groups. ) A general formula that is characterized by reacting with a compound shown in (However, R is as described above). ] A method for producing a disazo compound.