JP2010079015A - Dispersion for electrophotographic photoreceptor, and method for manufacturing electrophotographic photoreceptor - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a dispersion capable of suppressing the dispersion from turning into unstable or the membrane of an undercoat layer from becoming uneven caused by aggregation of pigment even when the undercoat layer is applied while a support body is heated, and to provide a method for manufacturing an electrophotographic photoreceptor using the dispersion for the electrophotographic photoreceptor. <P>SOLUTION: The dispersion for the electrophotographic photoreceptor is obtained by dispersing an organic pigment and a gelled polyamide resin in a solvent, wherein the gelled polyamide resin includes a gelled N-methoxymethylated nylon or a quaternary nylon copolymer of nylon 6-66-610-12, and the dispersion for an electrophotographic photoreceptor contains a secondary alcohol having an ether group. The method for manufacturing an electrophotographic photoreceptor is characterized by forming a photoreceptor by using the above dispersion for an electrophotographic photoreceptor. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a dispersion for an electrophotographic photoreceptor prepared using an organic pigment, a specific gelled polyamide resin, and a specific solvent, and a method for producing an electrophotographic photoreceptor using the dispersion.

  An electrophotographic photoreceptor includes a photosensitive layer that forms an electrostatic latent image by charging and exposure using light, and a support as a support member for providing the photosensitive layer. In general, when a photosensitive layer is directly formed on a support, unevenness of the photosensitive layer is caused by contamination of the surface of the support, uneven shape and properties, and the like. As a result, the obtained image may have image defects such as white spots, black spots, density unevenness, and a problem that the photosensitive layer is peeled off from the support.

  Up to now, an undercoat layer has been provided between the support and the photosensitive layer for the purpose of securing adhesion to the support, protecting electrical breakdown of the photosensitive layer, and improving charge injection from the support to the photosensitive layer. Things have been done. While this undercoat layer has the above-mentioned advantages, it also has the disadvantage that charges are likely to be accumulated in order to suppress charge transfer between the support and the photosensitive layer, such as an increase in residual potential during continuous printing in a low humidity environment. Potential fluctuations may occur and problems such as image density reduction may occur. Particularly in recent years, as the quality and speed of printers and copiers have increased, the requirements for the quality of electrophotographic photoreceptors have become stricter, and changes in usage environment and changes in potential fluctuations even during continuous use. There has been a strong demand for an electrophotographic photosensitive member that does not occur.

In order to suppress such inconveniences, methods for containing a metal oxide pigment or an organic pigment in the undercoat layer have been proposed (see Patent Documents 1 and 2). In these proposals, an undercoat layer is obtained by applying a dispersion in which an organic pigment or a metal oxide pigment is dispersed in an alcohol solution of an alcohol-soluble polyamide resin on a support.
International Publication No. 2005/116777 Pamphlet Japanese Patent Laid-Open No. 2000-221701

  However, during factory production, etc., the support is heated by ultrasonic cleaning or heat drying during application of other conductive layers, and the undercoat layer is applied onto the heated support. There are many. Accordingly, the dispersion for the undercoat layer comes into contact with a large number of heated supports, and the temperature of the dispersion rises to cause the aggregation of the pigment, thereby deteriorating the stability of the dispersion liquid. It may cause unevenness.

  In view of the above problems, the object of the present invention is to destabilize the dispersion due to the aggregation of the pigment and to generate film unevenness in the undercoat layer even when the undercoat layer is applied with the support heated. An object of the present invention is to provide a dispersion that can be suppressed and a method for producing an electrophotographic photosensitive member using the dispersion for an electrophotographic photosensitive member.

According to the present invention, a dispersion for an electrophotographic photoreceptor obtained by dispersing an organic pigment and a gelled polyamide resin in a solvent,
The gelled polyamide resin is a quaternary nylon copolymer of gelled N-methoxymethylated nylon or gelled nylon 6-66-610-12,
There is provided a dispersion for an electrophotographic photoreceptor, wherein the dispersion for an electrophotographic photoreceptor contains a secondary alcohol having an ether group.

According to the present invention, in the method for producing an electrophotographic photoreceptor by forming an undercoat layer and a photosensitive layer in this order on a support,
There is provided a method for producing an electrophotographic photosensitive member, wherein the undercoat layer is formed using the electrophotographic photosensitive member dispersion.

  The electrophotographic photoreceptor dispersion of the present invention and the method for producing an electrophotographic photoreceptor using the electrophotographic photoreceptor dispersion use a gelled polyamide resin, an organic pigment, and a secondary alcohol having an ether group. The dispersion prepared in this way is used. As a result, even when an undercoat layer is produced on the heated support using the dispersion liquid, it is possible to suppress the destabilization of the dispersion liquid due to the aggregation of the organic pigment and the film unevenness of the undercoat layer. A method for producing an electrophotographic photoreceptor using the dispersion for a photographic photoreceptor and the dispersion for an electrophotographic photoreceptor can be provided.

  Hereinafter, embodiments of the present invention will be described in detail.

  The dispersion liquid of the present invention is a dispersion liquid produced by dispersing an organic pigment and a gelled polyamide resin in a solvent.

  The “gelled polyamide resin” described here means a polyamide resin solution that can be determined to be in a solid state by performing a solid-liquid determination test in accordance with ASTM D4359-90 standard.

  The gelled polyamide resin can be prepared by combining the following conditions after the polyamide resin alone or the polyamide resin is dissolved by heating in a solvent.

  (1) Type of polyamide resin: The type of polyamide resin is determined in consideration of solubility in a solvent for gelling the polyamide resin and ease of gelation of the polyamide resin. As the types of polyamide resins, N-alkoxyalkylated nylon typified by N-methoxymethylated 6 nylon and N-methoxymethylated 12 nylon, and quaternary nylon copolymer of nylon 6-66-610-12 Nylon copolymer is more preferable. Most preferred is a quaternary nylon copolymer of N-methoxymethylated 6 nylon or nylon 6-66-610-12. One type or two or more types of polyamide resins can be used in combination. When at least N-methoxymethylated nylon is included, it is more preferable that N-methoxymethylated nylon having an N-methoxymethylation rate of 20% to 45% is included. In addition, N-methoxymethylation rate was measured by the method shown below by NMR. When N-methoxymethylated nylon has a N-methoxymethylation rate lower than 20%, solubility in a solvent may be lowered, and it may be difficult to prepare a gelled polyamide resin. When the N-methoxymethylation rate is higher than 45%, the solubility in a solvent increases, and the stability of the gelled polyamide resin may deteriorate.

<Measurement method of N-methoxymethylation rate>
apparatus:
Measuring apparatus: FT NMR apparatus JNM-EX400 (manufactured by JEOL Ltd.)
Measurement frequency: 400MHz
Pulse condition: 5.0 μS
Data points: 32768
Frequency range: 10500Hz
Integration count: 32 times Measurement temperature: 25 ° C
sample:
N-methoxymethylated nylon 25mg
0.75 ml of methanol-D4 (99.8 atom% D) made by Aldrich
Tetramethylsilane (internal standard) 0.05% by mass with respect to methanol-D4
Method of calculation:
A: Integral value of methylene proton (ca.2.4 ppm) adjacent to the carbonyl portion of the amide group which is N-methoxymethylated B: Methylene proton (ca) adjacent to the carbonyl portion of the amide group which is not N-methoxymethylated 2.2 ppm) N-methoxymethylation rate (%) = A / (A + B) × 100

  (2) Temperature at which the polyamide resin is gelled: The temperature at which the polyamide resin is gelled is not particularly limited as long as the desired gelled polyamide resin can be obtained. In order to obtain a gelled polyamide resin stably, it is preferable to cool the polyamide resin heated and dissolved at a certain concentration or higher in the solvent, and more preferably to 30 ° C. or lower.

  (3) Solvent for gelling the polyamide resin: The presence or type of the solvent is not particularly limited as long as the desired gelled polyamide resin can be prepared, but is preferably alcohol. In addition, the solvent may be combined with one or more solvents in consideration of the solubility of the polyamide resin and the ease of preparation of the gelled polyamide resin.

  The alcohol is more preferably a linear or branched alcohol having 1 to 6 carbon atoms, and particularly preferably contains any one of ethanol, n-propanol, and n-butanol.

  (4) Polyamide resin solid content of gelled polyamide resin: If a desired gelled polyamide resin can be prepared, the polyamide resin solid content of the gelled polyamide resin is not particularly limited. Considering the stability of the gelled polyamide resin, the solid content of the polyamide resin is preferably 2.0% or more by mass%, and most preferably in the range of 5.0% or more and 30.0% or less. If the solid content of the polyamide resin is too low, the gelled polyamide resin may not be prepared, and if it is too high, it may not be dissolved.

  (5) Shape of gelled polyamide resin: The shape of the gelled polyamide resin is not particularly limited as long as a desired dispersion can be prepared. Considering workability in the dispersion operation, it is preferable to crush the gelled polyamide resin into a mass of 0.5 mm or more and 10 mm or less before dispersion. If the gelled polyamide resin mass is smaller than 0.5 mm, the crushed gelled polyamide resins are likely to adhere to each other, and workability may be deteriorated. If the gelled polyamide resin mass is larger than 10 mm, an undispersed component of the gelled polyamide resin may remain after the dispersion is completed. For crushing the gelled polyamide resin, a paint shaker, a ball mill, a sand mill, an ultrasonic disperser, a high-pressure homogenizer, a stirrer, a mixer, a stirrer, a roll mill, an emulsion disperser, a mesh, a sieve, a mincer, or the like is used.

  As the organic pigment, conventionally known pigments such as azo pigments such as monoazo, bisazo, trisazo, and tetrakisazo, phthalocyanine pigments such as gallium phthalocyanine and titanyl phthalocyanine, and perylene pigments can be used. Among these, azo pigments are particularly preferable because they can interact with the amide bond of the polyamide resin through hydrogen bonds. Moreover, these organic pigments can be used in combination of two or more thereof.

  As the azo pigment, a bisazo pigment represented by the following general formula (1) is most preferable. Although the details are not clear as the most preferable reason, it is presumed that a good dispersion state can be maintained because the amide bond having affinity for the gelled polyamide resin and the hydroxyl group having affinity for alcohol are simultaneously present.

In general formula (1), Ar ¹ and Ar ² each independently represent a substituted or unsubstituted aryl group. X ¹ represents a vinylene group or a p-phenylene group. n represents 0 or 1.

  The dispersion is produced by dispersing the gelled polyamide resin and the organic pigment in a solvent. Considering the dispersibility of the dispersion, when the gelled polyamide resin and the organic pigment are dispersed, it is preferable to add a solvent to increase the fluidity of the dispersion during dispersion to some extent. The solvent, the organic pigment and the gelled polyamide resin may be dispersed simultaneously, or only the organic pigment may be dispersed in advance in the solvent, and then the gelled polyamide resin may be added and dispersed.

  As a dispersion method, a known method, for example, a method using a dispersion device such as a paint shaker, a ball mill, a sand mill, an ultrasonic disperser, a high-pressure homogenizer, a stirrer, a mixer, a stirrer, a roll mill, or an emulsifying disperser is used. Can do.

  The dispersion contains a secondary alcohol having an ether group. The secondary alcohol may be contained in a solvent used at the time of dispersing the organic pigment and the gelled polyamide resin, or may be contained at the stage of diluting the dispersion after completion of the dispersion. Furthermore, it is particularly preferred that at least one of the solvents used during dispersion is ethanol, n-propanol, or n-butanol.

  The content of the secondary alcohol having an ether group is preferably 10% by mass or more and 70% by mass or less with respect to the total mass of the electrophotographic photoreceptor dispersion. When the content of the secondary alcohol having an ether group is less than 10% by mass, the organic pigment tends to aggregate, and when it exceeds 70% by mass, the viscosity of the dispersion increases and the stability of the dispersion deteriorates. There is.

  As the secondary alcohol having an ether group, a glycol ether compound is preferable, and a propylene glycol monoalkyl ether compound is preferable. Among these, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, and propylene glycol monobutyl ether are preferably selected. Most preferred is propylene glycol monomethyl ether.

  As a result of intensive studies, we have found that the effect of improving the stability of the dispersion can be exhibited more significantly by combining the gelled polyamide resin and the secondary alcohol having an ether group. The reason is not clear, but the following can be considered. The secondary alcohol having an ether group is a solvent having low solubility in the polyamide resin, and has a property of easily affinity and mixing with the alcohol. Therefore, this property is presumed that a stable dispersion state can be maintained because the gelled polyamide resin dispersed together with the pigment is prevented from dissolving or shrinking in various environments.

  The mass ratio (P / B) of the mass (P) of the organic pigment contained in the electrophotographic photoreceptor dispersion and the mass (B) of the gelled polyamide resin is determined using the liquid stability of the dispersion and the dispersion. It is determined in consideration of the effect of suppressing potential fluctuations during continuous printing of the electrophotographic photosensitive member formed in this manner. Preferably, the mass ratio (P / B) of the mass (P) of the organic pigment contained in the dispersion and the mass (B) of the gelled polyamide resin is 1/1000 or more and 3/1 or less. More preferably, the mass ratio (P / B) of the mass (P) of the organic pigment contained in the dispersion and the mass (B) of the gelled polyamide resin is from 1/100 to 2/1. When the mass ratio of the organic pigment and the gelled polyamide resin contained in the dispersion is higher than 3/1, the dispersibility of the pigment may deteriorate and the liquid stability of the dispersion may deteriorate. Further, if the mass ratio of the organic pigment and the gelled polyamide resin contained in the dispersion is lower than 1/1000, the effect of suppressing potential fluctuations during continuous printing on the electrophotographic photosensitive member may be inferior.

  The solid content of the dispersion is determined in consideration of the stability and coating properties of the dispersion, and is preferably 1.0% or more and 20.0% or less, and more preferably 1.5% or more and 5.5% by mass. 0% or less. When the solid content of the dispersion is higher than 20.0%, the fluidity of the dispersion may be lost, or the dispersibility may be deteriorated and the liquid stability of the dispersion may be lowered. On the other hand, if the solid content of the dispersion is lower than 1%, uneven application of the electrophotographic photosensitive member using the dispersion, image density unevenness due to film sagging, and the like may be deteriorated.

  Next, a method for producing an electrophotographic photoreceptor formed using the dispersion of the present invention will be described.

  The electrophotographic photoreceptor is formed by laminating at least an undercoat layer and a photosensitive layer on a conductive support. Even if the photosensitive layer is a single-layer type photosensitive layer (FIG. 1A) containing the charge transport material and the charge generation material in the same layer, the charge generation layer and the charge transport material containing the charge generation material are used. Although it may be a laminated type (functionally separated type) photosensitive layer (FIG. 1B) separated into the contained charge transport layer, a laminated type photosensitive layer is preferred from the viewpoint of electrophotographic characteristics. 1A and 1B, reference numeral 101 denotes a support, 102 denotes an undercoat layer, 103 denotes a photosensitive layer, 104 denotes a charge generation layer, and 105 denotes a charge transport layer. In the following, an electrophotographic photoreceptor containing a laminated (functionally separated type) photosensitive layer will be described in detail.

  The conductive support only needs to have conductivity, and examples thereof include metals such as aluminum, stainless steel, and nickel, or metals provided with a conductive layer, plastics, paper, and the like. Can be mentioned. In particular, cylindrical aluminum is excellent in terms of mechanical strength, electrophotographic characteristics, and cost. These conductive supports may be used as they are, but those subjected to physical treatment such as cutting and honing, anodizing treatment, or chemical treatment using acid or the like may be used. Among them, by performing physical processing such as cutting or honing, the surface roughness is processed to be 0.1 μm or more and 3.0 μm or less in terms of Rz value, thereby providing an interference fringe prevention function.

  An interference fringe preventing layer (not shown in FIG. 1) may be provided between the conductive support and the undercoat layer. The interference fringe prevention layer is not necessary when the support itself has an interference fringe prevention function, but by using the conductive support as it is and forming an interference fringe prevention layer by coating on it, An interference fringe preventing function can be imparted to the conductive support by a simple method. For this reason, it is very useful in terms of productivity and cost. The interference fringe prevention layer was prepared by dispersing inorganic particles such as tin oxide, indium oxide, titanium oxide, and barium sulfate in a suitable solvent together with a curable resin such as a phenol resin, and coating the resultant on a support. Thereafter, it is formed by heating and drying. The film thickness of the interference fringe prevention layer is preferably 1 μm or more and 40 μm or less, and more preferably 10 μm or more and 30 μm or less from the viewpoint of interference fringe prevention ability and coating of defects on the support.

  On the support or the interference fringe preventing layer, an undercoat layer is necessary for securing adhesion to the support, protecting the photosensitive layer from electrical breakdown, improving the carrier injection property of the photosensitive layer, and the like.

  The undercoat layer is formed by coating the dispersion composed of an organic pigment and a gelled polyamide resin on a support or an interference fringe prevention layer. The film thickness is preferably 0.01 μm or more and 10 μm or less, and more preferably 0.1 μm or more and 5 μm or less. By including an organic pigment in the undercoat layer, potential fluctuations during continuous printing can be suppressed.

  The laminated photosensitive layer is preferably a layer in which a charge generation layer and a charge transport layer are laminated on an undercoat layer in this order.

  As the charge generation material contained in the charge generation layer, azo pigments such as monoazo, bisazo, trisazo and tetrakisazo, phthalocyanine pigments such as gallium phthalocyanine and titanyl phthalocyanine, and perylene pigments can be used. A gallium phthalocyanine pigment is preferable from the viewpoint of characteristic stability during environmental changes. More preferably, from the viewpoint of high sensitivity, a crystal type having strong peaks at Bragg angles 2θ = 7.4 ° ± 0.3 ° and 2θ = 28.2 ° ± 0.3 ° in CuKα characteristic X-ray diffraction. Of hydroxygallium phthalocyanine.

  The coating solution for the charge generation layer is prepared by the known dispersion method described above using the charge generation material as a suitable solvent. Suitable solvents include, for example, tetrahydrofuran, cyclohexanone, methyl ethyl ketone, ethyl acetate, methanol, methyl cellosolve, acetone, dioxane and N, N-dimethylformamide. At this time, a polymer substance may be added together as a binder, or the binder may be added after predispersing only with a pigment and a solvent.

  The binder can be selected from a wide range of insulating resins, and can also be selected from organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinyl anthracene, and polyvinyl porene. Preferable examples include insulating resins such as polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and phthalic acid, etc.), polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, and polyacrylamide resin. In addition, insulating resins such as polyamide, polyvinyl pyridine, cellulose resin, urethane resin, epoxy resin, casein, polyvinyl alcohol, and polyvinyl pyrrolidone can be given.

  The charge generation layer is formed by applying a dispersion containing the above substances on the undercoat layer and then drying by heating. The thickness of the charge generation layer is preferably 5 μm or less, particularly preferably 0.05 μm or more and 1 μm or less. .

  The charge transport layer is formed by applying a paint in which a charge transport material and a binder are dissolved in a solvent, followed by heating and drying.

  Examples of the charge transport material used include various triarylamine compounds, hydrazone compounds, stilbene compounds, pyrazoline compounds, oxazole compounds, thiazole compounds, triallylmethane compounds, and the like. A binder may be added after preliminarily dispersing and dissolving only with the charge transport material and the solvent. Moreover, what was mentioned above can be used as a binder.

  The thickness of the charge transport layer is preferably 5 μm or more and 40 μm or less, and more preferably 10 μm or more and 30 μm or less.

  When the charge transport layer is a single layer, it can be formed similarly using the above-described substances, and the film thickness is preferably 5 μm or more and 40 μm or less, and particularly preferably 10 μm or more and 30 μm or less.

  In the present invention, a protective layer may be provided on the charge transport layer for the purpose of improving durability, transferability and cleaning properties (not shown in FIG. 1).

  The protective layer can be formed by applying and drying a protective layer coating solution obtained by dissolving a resin in an organic solvent. Examples of the resin include polyvinyl butyral, polyester, polycarbonate, polyamide, polyimide, polyarylate, polyurethane, styrene-butadiene copolymer, styrene-acrylic acid copolymer, and styrene-acrylonitrile copolymer.

  Further, in order to provide the protective layer with the charge transport ability, the protective layer may be formed by curing a monomer material having a charge transport ability or a polymer type charge transport material using various crosslinking reactions. . Examples of the curing reaction include radical polymerization, ionic polymerization, thermal polymerization, photopolymerization, radiation polymerization (electron beam polymerization), plasma CVD method, and photo CVD method.

  Furthermore, you may include electroconductive particle, a ultraviolet absorber, an abrasion resistance improving agent, etc. in a protective layer. As the conductive particles, for example, metal oxides such as tin oxide particles are preferable. As the wear resistance improver, fluorine resin fine powder, alumina, silica and the like are preferable.

  The thickness of the protective layer is preferably 0.5 μm or more and 20 μm or less, and particularly preferably 1 μm or more and 10 μm or less.

  As a coating method for these various layers, a dipping method, a spray coating method, a spinner coating method, a bead coating method, a blade coating method, a beam coating method, and the like can be used.

  Hereinafter, the present invention will be described in more detail with reference to specific examples. However, embodiments of the present invention are not limited to these. In the examples, “parts” means “parts by mass”.

  First, a method for producing the dispersion of the present invention will be described.

<Production Example 1 of Gelled Polyamide Resin>
22.5 parts of N-methoxymethylated 6 nylon resin (trade name: Toresin EF-30T, manufactured by Nagase ChemteX Corporation, degree of polymerization 420, methoxymethylation rate 36.8%), ethanol (made by Kishida Chemical, special grade) The mixture was dissolved in 127.5 parts while stirring in a 60 ° C. hot water bath. Next, the solution was allowed to stand in an environment having a temperature of 23 ° C. and a relative humidity of 50% for 12 hours to obtain a gelled polyamide resin GA-1.

<Production Example 2 of Gelled Polyamide Resin>
15.0 parts of N-methoxymethylated 6 nylon resin (trade name: Toresin EF-30T, manufactured by Nagase ChemteX Corp., degree of polymerization 420, methoxymethylation rate 36.8%) was added to n-butanol (manufactured by Kishida Chemical, Special grade) 135.0 parts were dissolved with stirring in a 70 ° C hot water bath. The solution was then allowed to stand for 12 hours in an environment having a temperature of 23 ° C. and a relative humidity of 50% to obtain a gelled polyamide resin GA-2.

<Production Example 3 of Gelled Polyamide Resin>
Nylon 6-66-610-12 Quaternary nylon copolymer resin (trade name: CM8000, manufactured by Toray Industries, Inc.) 22.5 parts, isobutanol (manufactured by Kishida Chemical, special grade) 127.5 parts, 70 ° C. hot water bath The solution was stirred and dissolved with heating. Next, the solution was allowed to stand in an environment having a temperature of 23 ° C. and a relative humidity of 50% for 12 hours to obtain a gelled polyamide resin GA-3.

<Production Example 4 of Gelled Polyamide Resin>
15.0 parts of N-methoxymethylated 6 nylon resin (trade name: Toresin EF-30T, manufactured by Nagase ChemteX Corporation, degree of polymerization 420, methoxymethylation rate 36.8%) was added to 2-propanol (manufactured by Kishida Chemical, Special grade) 135.0 parts were dissolved with stirring in a 70 ° C hot water bath. Next, the solution was allowed to stand in an environment having a temperature of 23 ° C. and a relative humidity of 50% for 12 hours to obtain a gelled polyamide resin GA-4.

<Production Example 5 of Gelled Polyamide Resin>
15.0 parts of N-methoxymethylated 6 nylon resin (trade name: Toresin EF-30T, manufactured by Nagase ChemteX Corporation, degree of polymerization 420, methoxymethylation rate 36.8%), 2-butanol (manufactured by Kishida Chemical, Special grade) 135.0 parts were dissolved with stirring in a 70 ° C hot water bath. The solution was then allowed to stand for 12 hours in an environment having a temperature of 23 ° C. and a relative humidity of 50% to obtain a gelled polyamide resin GA-5.

<Production Example 6 of Gelled Polyamide Resin>
15.0 parts of N-methoxymethylated 6 nylon resin (trade name: Toresin EF-30T, manufactured by Nagase ChemteX Corporation, degree of polymerization 420, methoxymethylation rate 36.8%) was added to n-propanol (manufactured by Kishida Chemical, Special grade) 135.0 parts were dissolved with stirring in a 70 ° C hot water bath. The solution was then allowed to stand for 12 hours in an environment having a temperature of 23 ° C. and a relative humidity of 50% to obtain a gelled polyamide resin GA-6.

  Next, examples relating to the preparation of the dispersion are shown.

<Example 1>
130.0 parts of the gelled polyamide resin GA-3 was crushed to a size of 1 mm or less by crushing while crushing with a sieve (mesh opening 0.5 mm). to this,
Isobutanol (manufactured by Kishida Chemical Co., Ltd., special grade) 50.0 parts 0.098 parts of a hydroxygallium phthalocyanine pigment represented by the following formula (2) (flag angle 2θ = 7.4 ° ± 0.3 ° in CuKα characteristic X-ray diffraction) Crystalline gallium phthalocyanine having a strong peak at a position of 2θ = 28.2 ° ± 0.3 ° (as described in Japanese Patent No. 3639691))

Was added to obtain a mixed solution before dispersion. This mixed liquid was dispersed using a vertical sand mill, using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotational speed of 1500 rpm (circumferential speed 5.5 m / s) for 4 hours. A liquid 1-1 was obtained. To dispersion 1-1, 441.5 parts of isobutanol (manufactured by Kishida Chemical, special grade) and 31.7 parts of propylene glycol monopropyl ether (manufactured by Toho Chemical Industry) were added and diluted to obtain dispersion 1-A. .

  Using a centrifugal sedimentation type particle size distribution analyzer CAPA-700 (manufactured by Horiba Seisakusho), the average particle size (median diameter) of the dispersion 1-A at room temperature (23 ° C.) is measured under the following measurement conditions. did. Further, after the dispersion 1-A was stored in a constant temperature bath at 40 ° C. for 1 hour, the particle size was measured in the same manner. The results are shown in Table 1.

<Measurement conditions of dispersion particle size>
(Particle size calculation conditions)
Calculation method: Volume-based settling distance: ΔX = 10 mm
Absorption coefficient correction: No correction (measurement conditions)
Solvent Ethanol DISP. VISC. 1.20 mPa · s
DISP. DENS. 0.79g / cc
SAMP. DENS. 1.20g / cc
D (MAX) 1.00μm
D (MIN) 0.10 μm
D (DIV) 0.05 μm
SPEED 7000rpm

<Example 2>
As the gelled polyamide resin, GA-4, 2-propanol (made by Kishida Chemical, special grade) was used instead of isobutanol, and propylene glycol monoethyl ether (made by Toho Chemical Industry) was used instead of propylene glycol monopropyl ether. . Otherwise, dispersion and dilution were performed in the same manner as in Example 1 to obtain dispersion 2-A. The above particle size measurement was performed on the dispersion 2-A. The results are shown in Table 1.

<Example 3>
130.0 parts of the gelled polyamide resin GA-1 was crushed into a size of 1 mm or less by crushing while crushing with a sieve (aperture opening 0.5 mm). To this, 16.2 parts of ethanol (manufactured by Kishida Chemical Co., Ltd.) and 0.098 parts of hydroxygallium phthalocyanine pigment represented by the above formula (2) were added to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 3-1 was obtained.

  To dispersion 3-1, 459.8 parts of ethanol (made by Kishida Chemical, special grade) and 32.7 parts of propylene glycol monoethyl ether (made by Kishida Chemical) were added and diluted to obtain dispersion 3-A. The above particle size measurement was performed on the dispersion 3-A. The results are shown in Table 1.

<Example 4>
130.0 parts of the gelled polyamide resin GA-5 was crushed to a size of 1 mm or less by crushing while crushing with a sieve (aperture opening 0.5 mm). To this, 50.0 parts of 2-butanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 0.098 parts of hydroxygallium phthalocyanine pigment represented by the above formula (2) were added to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 4-1 was obtained.

  To dispersion 4-1, 213.2 parts of 2-butanol (manufactured by Kishida Chemical, special grade) and 42.2 parts of propylene glycol monoethyl ether (product of Kishida Chemical) were added and diluted to obtain dispersion 4-A. . The above particle size measurement was performed on the dispersion 4-A. The results are shown in Table 1.

<Example 5>
130.0 parts of the gelled polyamide resin GA-5 was crushed to a size of 1 mm or less by crushing while crushing with a sieve (aperture opening 0.5 mm). To this, 9.7 parts of 2-butanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 0.065 parts of hydroxygallium phthalocyanine pigment represented by the above formula (2) were added to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 5-1 was obtained.

  295.7 parts of propylene glycol monoethyl ether (manufactured by Kishida Chemical Co., Ltd.) was added to the dispersion 5-1, and diluted to obtain dispersion 5-A. The above particle size measurement was performed on the dispersion 5-A. The results are shown in Table 1.

<Example 6>
130.0 parts of the gelled polyamide resin GA-1 was crushed to a size of 1 mm or less by crushing while crushing with a sieve (mesh opening 0.5 mm). To this, 50.0 parts of ethanol (manufactured by Kishida Chemical Co., Ltd.) and 0.098 parts of hydroxygallium phthalocyanine pigment represented by the above formula (2) were added to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 6-1 was obtained.

  To dispersion 6-1, 219.7 parts of ethanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 253.5 parts of propylene glycol monobutyl ether (manufactured by Toho Chemical Industry) were added and diluted to obtain dispersion 6-A. The above particle size measurement was performed on the dispersion 6-A. The results are shown in Table 1.

<Example 7>
130.0 parts of the gelled polyamide resin GA-5 was crushed to a size of 1 mm or less by crushing while crushing with a sieve (aperture opening 0.5 mm). To this, 50.0 parts of 2-butanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 0.065 parts of hydroxygallium phthalocyanine pigment represented by the above formula (2) were added to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 7-1 was obtained.

  To dispersion 7-1, 170.9 parts of 2-butanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 84.5 parts of propylene glycol monomethyl ether (manufactured by Kishida Chemical Co., Ltd., first grade) were added and diluted to prepare dispersion 7-A. Obtained. The above particle size measurement was performed on the dispersion 7-A. The results are shown in Table 1.

<Example 8>
130.0 parts of the gelled polyamide resin GA-1 was crushed to a size of 1 mm or less by crushing while crushing with a sieve (mesh opening 0.5 mm). To this, 50.0 parts of ethanol (manufactured by Kishida Chemical Co., Ltd.) and 0.098 parts of hydroxygallium phthalocyanine pigment represented by the above formula (2) were added to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 8-1 was obtained.

  346.4 parts of ethanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 126.7 parts of propylene glycol monomethyl ether (manufactured by Kishida Chemical Co., Ltd., first grade) were added to the dispersion 8-1 and diluted to obtain a dispersion 8-A. . The above particle size measurement was performed on the dispersion 8-A. The results are shown in Table 1.

<Example 9>
130.0 parts of the gelled polyamide resin GA-1 was crushed to a size of 1 mm or less by crushing while crushing with a sieve (mesh opening 0.5 mm). To this, 50.0 parts of ethanol (manufactured by Kishida Chemical Co., Ltd.) and 0.098 parts of hydroxygallium phthalocyanine pigment represented by the above formula (2) were added to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 9-1 was obtained.

  To dispersion 9-1, 219.7 parts of ethanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 253.5 parts of propylene glycol monomethyl ether (manufactured by Kishida Chemical Co., Ltd., first grade) were added and diluted to obtain dispersion 9-A. . The above particle diameter measurement was performed on the dispersion 9-A. The results are shown in Table 1.

<Example 10>
130.0 parts of the gelled polyamide resin GA-1 was crushed to a size of 1 mm or less by crushing while crushing with a sieve (mesh opening 0.5 mm). To this, 50.0 parts of ethanol (manufactured by Kishida Chemical Co., Ltd.) and 0.098 parts of hydroxygallium phthalocyanine pigment represented by the above formula (2) were added to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 10-1 was obtained.

  To dispersion 10-1, 93.0 parts of ethanol (manufactured by Kishida Chemical, special grade) and 380.2 parts of propylene glycol monomethyl ether (manufactured by Kishida Chemical, first grade) were added and diluted to obtain dispersion 10-A. . The above particle size measurement was performed on the dispersion 10-A. The results are shown in Table 1.

<Example 11>
130.0 parts of the gelled polyamide resin GA-6 was crushed to a size of 1 mm or less by crushing while crushing with a sieve (aperture opening 0.5 mm). To this, 50.0 parts of n-propanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 0.098 parts of a hydroxygallium phthalocyanine pigment represented by the above formula (2) were added to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 11-1 was obtained.

  To dispersion 11-1, 170.9 parts of n-propanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 84.5 parts of propylene glycol monomethyl ether (manufactured by Kishida Chemical Co., Ltd., first grade) are added and diluted to prepare dispersion 11-A. Obtained. The above particle size measurement was performed on the dispersion 11-A. The results are shown in Table 1.

<Example 12>
Dispersion and dilution were carried out in the same manner as in Example 11 except that n-butanol (manufactured by Kishida Chemical Co., Ltd., special grade) was used as the gelling polyamide resin instead of GA-2 and n-propanol. -A was obtained. The above particle size measurement was performed on the dispersion 12-A. The results are shown in Table 1.

<Example 13>
130.0 parts of the gelled polyamide resin GA-1 was crushed to a size of 1 mm or less by crushing while crushing with a sieve (mesh opening 0.5 mm). to this,
Ethanol (manufactured by Kishida Chemical, special grade) 50.0 parts 0.130 parts of diazo compound represented by the following formula (3)

Were added to obtain a mixed solution before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 13-1 was obtained.

  To dispersion 13-1, 220.3 parts of ethanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 253.9 parts of propylene glycol monomethyl ether (manufactured by Kishida Chemical Co., Ltd., first grade) 253.9 parts were added and diluted to obtain dispersion 13-A. . The above particle diameter measurement was performed on the dispersion 13-A. The results are shown in Table 1.

<Example 14>
0.195 parts of the diazo compound represented by the above formula (3), 221.6 parts of ethanol (manufactured by Kishida Chemical Co., Ltd., special grade), propylene glycol monomethyl ether (manufactured by Kishida Chemical Co., Ltd., first grade) 254. Seven parts were used. Otherwise, dispersion and dilution were carried out in the same manner as in Example 13 to obtain dispersion 14-A. The results are shown in Table 1.

<Example 15>
6.50 parts of the diazo compound represented by the above formula (3), 343.9 parts of ethanol (manufactured by Kishida Chemical Co., Ltd., special grade), and propylene glycol monomethyl ether (manufactured by Kishida Chemical Co., Ltd., first grade) 336. Three parts were used. Otherwise, dispersion and dilution were carried out in the same manner as in Example 13 to obtain dispersion 15-A. The results are shown in Table 1.

<Example 16>
6.50 parts of the diazo compound represented by the above formula (3), 91.7 parts of ethanol (manufactured by Kishida Chemical Co., Ltd., special grade) as a dilution solvent after dispersion, 588. Five parts were used. Otherwise, dispersion and dilution were carried out in the same manner as in Example 13 to obtain dispersion 16-A. The results are shown in Table 1.

<Example 17>
6.50 parts of the diazo compound represented by the above formula (3), 596.1 parts of ethanol (manufactured by Kishida Chemical, special grade) as a diluent solvent after dispersion, 84. propylene glycol monomethyl ether (manufactured by Kishida Chemical, first grade) 84. One part was used. Other than that was disperse | distributed and diluted like Example 13, and dispersion liquid 17-A was obtained. The results are shown in Table 1.

<Example 18>
The gelled polyamide resin GA-1 was crushed to a size of 1 mm or less by filtering while crushing 80.0 parts of the gelled polyamide resin GA-1 with a sieve (aperture opening 0.5 mm). To this, 100.0 parts of ethanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 12.0 parts of a diazo compound represented by the above formula (3) were added to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 18-1 was obtained.

  To dispersion 18-1, 530.4 parts of ethanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 253.9 parts of propylene glycol monomethyl ether (manufactured by Kishida Chemical Co., Ltd., first grade) 253.9 parts were diluted to obtain dispersion 18-A. . The above particle diameter measurement was performed on the dispersion 18-A. The results are shown in Table 1.

<Example 19>
By crushing 60.0 parts of the gelled polyamide resin GA-1 with a sieve (a sieve opening of 0.5 mm), the powder was crushed to a size of 1 mm or less. 150.0 parts of ethanol (manufactured by Kishida Chemical Co., Ltd.) and 18.0 parts of the diazo compound represented by the above formula (3) were added thereto to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 19-1 was obtained.

  To dispersion 19-1, 322.8 parts of ethanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 349.2 parts of propylene glycol monomethyl ether (manufactured by Kishida Chemical Co., Ltd., first grade) were added and diluted to obtain dispersion liquid 19-A. . The above particle size measurement was performed on the dispersion 19-A. The results are shown in Table 1.

<Example 20>
The gelled polyamide resin GA-1 was crushed into a size of 1 mm or less by filtering while crushing 40.0 parts of the gelled polyamide resin GA-1 with a sieve (aperture opening 0.5 mm). 150.0 parts of ethanol (manufactured by Kishida Chemical Co., Ltd.) and 18.0 parts of the diazo compound represented by the above formula (3) were added thereto to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). A liquid 20-1 was obtained.

  To dispersion 20-1, 281.6 parts of ethanol (manufactured by Kishida Chemical, special grade) and 310.4 parts of propylene glycol monomethyl ether (manufactured by Kishida Chemical, first grade) were added and diluted to obtain dispersion 20-A. . The above particle diameter measurement was performed on the dispersion 20-A. The results are shown in Table 1.

<Example 21>
Dispersion and dilution were carried out in the same manner as in Example 13 except that a diazo compound represented by the following formula (4) was used instead of the diazo compound represented by the above formula (3). Obtained. The above particle diameter measurement was performed on the dispersion liquid 21-A. The results are shown in Table 1.

<Comparative Example 1>
Dispersion and dilution were carried out in the same manner as in Example 8 except that propylene glycol dimethyl ether was used instead of propylene glycol monomethyl ether to obtain dispersion 1-X. The results are shown in Table 1.

<Comparative example 2>
Dispersion and dilution were carried out in the same manner as in Example 8 except that ethylene glycol monomethyl ether was used instead of propylene glycol monomethyl ether to obtain dispersion 2-X. The above particle size measurement was performed on the dispersion 2-X. The results are shown in Table 1.

<Comparative Example 3>
19.5 parts of N-methoxymethylated 6 nylon resin (trade name: Toresin EF-30T, manufactured by Nagase ChemteX Corporation, degree of polymerization 420, methoxymethylation rate 36.8%), ethanol (made by Kishida Chemical, special grade) The mixture was dissolved with stirring in 370.5 parts while heating in a 60 ° C. hot water bath. Then, it stood to cool and obtained the polyamide resin ethanol solution. To this, 6.5 parts of the diazo compound represented by the above formula (3) was added to obtain a mixed liquid before dispersion. Using a vertical sand mill, this mixed solution was dispersed for 4 hours using 500 parts of glass beads having an average particle diameter of 1.0 mm as a dispersion medium at a rotation speed of 1500 rpm (circumferential speed 5.5 m / s). Liquid 3-11 was obtained. Dispersion 3-11 was diluted by adding 301.9 parts of ethanol (manufactured by Kishida Chemical Co., Ltd., special grade) and 168.1 parts of propylene glycol monomethyl ether (manufactured by Kishida Chemical Co., Ltd., first grade) to obtain dispersion 3-X. . The above particle size measurement was performed on the dispersion 3-X. The results are shown in Table 1.

  Next, an electrophotographic photoreceptor was produced using the dispersions 1-A to 20-A obtained above and 1-X, 2-X, 3-X.

<Embodiment 22 of electrophotographic photosensitive member>
50 parts of titanium oxide powder coated with tin oxide (trade name Kronos ECT-62, manufactured by Titanium Industry Co., Ltd.)
Resol type phenolic resin 25 parts Methyl cellosolve 20 parts Spherical silicone resin powder 3.8 parts (trade name Tospearl 120, manufactured by Toshiba Silicone Co., Ltd.)
Methanol 5 parts Silicone oil 0.002 parts (polydimethylsiloxane / polyoxyalkylene copolymer, average molecular weight 3000)
With the above configuration, the coating solution for interference fringe prevention layer was prepared by dispersing for 2 hours in a sand mill using glass beads having a diameter of 0.8 mm. This coating solution was dip-coated on an aluminum cylinder (diameter 30 mm, drawn tube) as a conductive support and dried at 140 ° C. for 30 minutes to form an interference fringe preventing layer having a thickness of 15 μm.

  The dispersion 1-A is dip-coated on the obtained interference fringe prevention layer and dried at 100 ° C. for 10 minutes to form an undercoat layer having a film thickness of 0.5 μm. 1 was obtained. The temperature of the aluminum cylinder on which the interference fringe preventing layer of this dip coating was formed was 40 ° C.

next,
10 parts of hydroxygallium phthalocyanine represented by the above formula (2) 0.1 part of a compound represented by the following formula (5)

And 5 parts of polyvinyl butyral resin (trade name: ESREC BX-1, manufactured by Sekisui Chemical Co., Ltd.) were added to 250 parts of cyclohexanone and dispersed in a sand mill apparatus using glass beads having a diameter of 0.8 mm for 3 hours. Strong at Bragg angles (2θ ± 0.2 °) of 7.5 °, 9.9 °, 16.3 °, 18.6 °, 25.1 ° and 28.3 ° in CuKα characteristic X-ray diffraction A crystalline form of hydroxygallium phthalocyanine dispersion having a peak was obtained. To this, 100 parts of cyclohexanone and 450 parts of ethyl acetate were further added and diluted to obtain a coating solution for charge generation layer. The obtained coating solution was dip-coated on the undercoat layer and dried at 100 ° C. for 10 minutes to form a charge generation layer having a thickness of 0.18 μm.

  Next, 10 parts of a charge transport material represented by the following formula (6),

10 parts of a polycarbonate resin (trade name: Iupilon Z-200, manufactured by Mitsubishi Engineering Plastics) was dissolved in 70 parts of monochlorobenzene. The obtained solution was dip-coated on the charge generation layer and dried at 110 ° C. for 1 hour to form a charge transport layer having a thickness of 25 μm, thereby producing an electrophotographic photosensitive member D-1.

<Electrophotographic photoconductor production examples 23 to 42>
Undercoating layer coating cylinder C in the same manner as in Production Example 1 of the electrophotographic photosensitive member, except that the dispersion applied on the interference fringe prevention layer was changed from 1-A to 2-A to 21-A. -2 to C-21 and electrophotographic photoreceptors D-2 to D-21 were prepared.

<Production Comparative Examples 4 to 6 of electrophotographic photoreceptor>
Undercoating is performed in the same manner as in Production Example 1 of the electrophotographic photosensitive member, except that the dispersion applied on the obtained interference fringe prevention layer is changed from 1-A to 1-X, 2-X, 3-X. Layer coating cylinders 1-Y, 2-Y, 3-Y and electrophotographic photoreceptors 1-Z, 2-Z, 3-Z were prepared.

(Undercoat layer unevenness evaluation example)
<Examples 22 to 42>
The undercoat layer coating cylinders C-1 to C-21 prepared above were evaluated for the presence or absence of the undercoat layer film by visually observing the undercoat layer application surface. The visual evaluation results were performed based on the following criteria. The results are shown in Table 2.
(Undercoating layer film unevenness judgment criteria)
1 ... no unevenness 2 ... thin unevenness in the major axis direction less than about 2 mm wide 3 ... one or more thin unevenness in the major axis direction about 2 mm wide 4 or more 3 mm width or more Long-axis unevenness

<Comparative Examples 4 to 6>
The undercoat layer coating cylinders 1-Y, 2-Y, and 3-Y produced above were evaluated by visually observing the undercoat layer application surface for the presence or absence of the undercoat layer film. The determination of the evaluation result was the same as in Examples 22 to 42 described above. The results are shown in Table 2.

(Example of photoreceptor unevenness evaluation)
<Examples 22 to 42>
Next, the electrophotographic photoreceptors D-1 to D-21 prepared in a digital copying machine IR-400 manufactured by Canon Inc. were mounted and image evaluation was performed.

  The evaluation results are “no unevenness” when no unevenness is observed on the image, “some unevenness” when unevenness is recognized on the image, and “all unevenness” when unevenness is recognized on the image. It was. The results are shown in Table 2.

<Comparative Examples 4 to 6>
In the same manner as in Example 22, the electrophotographic photosensitive members 1-Z, 2-Z, and 3-Z prepared in a digital copying machine IR-400 manufactured by Canon Inc. were mounted and image evaluation was performed. The determination of the evaluation result was the same as in Examples 22 to 42. The results are shown in Table 2.

  As can be seen from Table 1, Examples 1 to 21 of dispersions prepared with an organic pigment, a gelled polyamide resin, and a solvent and containing a secondary alcohol having an ether group are organic pigments. And Comparative Example 3 of an electrophotographic photosensitive member using a dispersion obtained by dispersing a non-gelling polyamide resin, and Comparative Examples 1 and 2 containing an alcohol that is not a secondary alcohol having an ether group It can be seen that the dispersion is excellent in stability at room temperature and warming.

  Further, as is apparent from Table 2, Examples 22 to 42 of dispersions prepared with an organic pigment, a gelled polyamide resin and a solvent and obtained by containing a secondary alcohol having an ether group, Comparative Example 6 of an electrophotographic photosensitive member using a dispersion obtained by dispersing an organic pigment and a non-gelled polyamide resin, and Comparative Examples 4, 5 containing an alcohol that is not a secondary alcohol having an ether group Compared with the results of visual confirmation of the undercoat cylinder and the electrophotographic photoreceptor, it can be seen that coating film unevenness is suppressed.

It is a figure which shows the structure of a photosensitive layer. 1 is a diagram illustrating an example of a schematic configuration of an electrophotographic apparatus including a process cartridge having the electrophotographic photosensitive member of the present invention.

Explanation of symbols

DESCRIPTION OF SYMBOLS 101 Support body 102 Undercoat layer 103 Photosensitive layer 104 Charge generation layer 105 Charge transport layer 1 Electrophotographic photosensitive member 2 Axis 3 Charging means 4 Exposure light 5 Developing means 6 Transfer means 7 Transfer material 8 Fixing means 9 Cleaning means 10 Pre-exposure light 11 Process cartridge 12 Guide means

Claims (7)

A dispersion for an electrophotographic photoreceptor obtained by dispersing an organic pigment and a gelled polyamide resin in a solvent,
The gelled polyamide resin is a quaternary nylon copolymer of gelled N-methoxymethylated 6 nylon or gelled nylon 6-66-610-12,
The dispersion for electrophotographic photoreceptors, wherein the dispersion for electrophotographic photoreceptors contains a secondary alcohol having an ether group.   The dispersion for an electrophotographic photosensitive member according to claim 1, wherein the content of the secondary alcohol having an ether group is 10% by mass or more and 70% by mass or less based on the total mass of the dispersion for the electrophotographic photosensitive member. liquid.   The electrophotographic photosensitive member dispersion according to claim 1, wherein the secondary alcohol having an ether group is propylene glycol monomethyl ether.   4. The electrophotographic photosensitive member dispersion according to claim 1, wherein at least one of the solvents is ethanol, n-propanol, or n-butanol. The dispersion for an electrophotographic photosensitive member according to claim 1, wherein the organic pigment is an azo pigment represented by the following general formula (1).

[In General Formula (1), Ar ¹ and Ar ² each independently represent a substituted or unsubstituted aryl group. X ¹ represents a vinylene group or a p-phenylene group. n represents 0 or 1. ]   The mass ratio (P / B) of the mass (P) of the organic pigment and the mass (B) of the gelled polyamide resin in the dispersion for the electrophotographic photoreceptor is 1/100 or more and 2/1 or less. The electrophotographic photosensitive member dispersion according to any one of claims 1 to 5. In a method for producing an electrophotographic photoreceptor by forming an undercoat layer and a photosensitive layer in this order on a support,
A method for producing an electrophotographic photosensitive member, wherein the undercoat layer is formed using the dispersion for an electrophotographic photosensitive member according to any one of claims 1 to 6.