WO2012111672A1 - 電子写真用感光体、その製造方法および電子写真装置 - Google Patents
電子写真用感光体、その製造方法および電子写真装置 Download PDFInfo
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- WO2012111672A1 WO2012111672A1 PCT/JP2012/053410 JP2012053410W WO2012111672A1 WO 2012111672 A1 WO2012111672 A1 WO 2012111672A1 JP 2012053410 W JP2012053410 W JP 2012053410W WO 2012111672 A1 WO2012111672 A1 WO 2012111672A1
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G15/00—Apparatus for electrographic processes using a charge pattern
- G03G15/06—Apparatus for electrographic processes using a charge pattern for developing
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0532—Macromolecular bonding materials obtained by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0542—Polyvinylalcohol, polyallylalcohol; Derivatives thereof, e.g. polyvinylesters, polyvinylethers, polyvinylamines
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0589—Macromolecular compounds characterised by specific side-chain substituents or end groups
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0696—Phthalocyanines
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/07—Polymeric photoconductive materials
- G03G5/071—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/07—Polymeric photoconductive materials
- G03G5/071—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G5/072—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising pending monoamine groups
- G03G5/0732—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising pending monoamine groups comprising pending alkenylarylamine
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/14—Inert intermediate or cover layers for charge-receiving layers
Definitions
- the present invention relates to an electrophotographic photosensitive member (hereinafter also simply referred to as “photosensitive member”) having a photosensitive layer containing an organic material, which is used in an electrophotographic apparatus such as an electrophotographic printer, a copying machine, or a facsimile, and its manufacture.
- the present invention relates to a method and an electrophotographic apparatus.
- the present invention relates to a laminate-type and single-layer type electrophotographic photoreceptor having excellent image characteristics and electrical characteristics by improving a resin binder which is a constituent material of the photosensitive layer, a method for producing the same, and an electrophotographic apparatus. .
- an electrophotographic photoreceptor is required to have a function of holding surface charges in a dark place, a function of receiving light to generate charges, and a function of receiving light and transporting charges.
- an electrophotographic photoreceptor a so-called laminated type in which functionally separated layers are laminated to a layer mainly contributing to charge generation and a layer contributing to surface charge retention in the dark and charge transport during light reception.
- the Carlson method is applied to image formation by electrophotography using these electrophotographic photoreceptors.
- image formation was performed by charging the photoconductor in the dark, and forming an electrostatic latent image on the charged photoconductor surface by exposure corresponding to the characters and pictures of the document.
- the electrostatic latent image is developed by toner, and the developed toner image is transferred and fixed to a support such as paper. After the toner image has been transferred, the photoreceptor is used again after removal of residual toner, neutralization, and the like.
- an inorganic photoconductive material such as selenium, selenium alloy, zinc oxide or cadmium sulfide.
- organic photoconductive materials for example, poly-N-vinylcarbazole, 9,10-anthracenediol polyester, pyrazoline, hydrazone, stilbene, butadiene, benzidine, phthalocyanine and bisazo compounds are known.
- the above-described function-separated stacked type photoreceptor in which a photosensitive layer is formed by laminating a charge generation layer containing a charge generation material and a charge rotation layer containing a charge rotation material, is an organic material. Against the backdrop of abundance, it has become mainstream due to its large design freedom based on the wide selectivity of materials suitable for each function of the photosensitive layer.
- a layer formed by dip coating using a coating solution in which an organic low molecular weight compound having a charge transfer function is dispersed or dissolved in a resin binder is used as a charge transport layer on this layer.
- Many photoreceptors have been commercialized.
- the charge generation layer is generally formed of a layer made of a dispersion in which an organic photoconductive material such as a phthalocyanine compound is dispersed in a resin binder as a charge generation material.
- an organic photoconductive material such as a phthalocyanine compound
- Patent Document 1 and Patent Document 2 polyvinyl acetal resin and polyvinyl butyral resin have good dispersibility of the pigment in the coating solution at the time of producing the photoreceptor and excellent adhesion.
- Patent Document 3 various methods for synthesizing the polyvinyl acetal resin itself have been studied.
- Patent Document 4 a charge generation layer containing two kinds of polyvinyl butyral resins having different butyralization degrees and two kinds of polyvinyl butyral resins having different hydroxyl contents in a specific mixing ratio is studied. Although effective in improving the stability and sensitivity in a high-humidity environment, the transfer resistance has not been studied.
- Patent Document 5 a combination of polyamide as the binder for the undercoat layer and polyvinyl butyral resin as the binder for the charge generation layer
- Patent Document 6 copolymer nylon as the binder for the undercoat layer and polyvinyl as the binder for the charge generation layer
- Patent Document 7 discloses a laminate composed of a layer of a curable resin composition containing a specific modified polyvinyl acetal resin and a base material layer, and a polyvinyl acetal resin containing a phenyl group is disclosed.
- an object of the present invention is to provide an electrophotographic photoreceptor having high transfer resistance, high memory characteristics, and good electrical characteristics, a method for producing the same, and an electrophotographic apparatus by solving the above problems.
- the present inventor uses a polyvinyl acetal resin containing a phenyl group as a constituent monomer for the photosensitive layer, and particularly uses a polyvinyl acetal resin containing such a phenyl group-containing unit in a specific ratio for the photosensitive layer.
- the inventors have found that the above problems can be solved, and have completed the present invention.
- the electrophotographic photoreceptor of the present invention is an electrophotographic photoreceptor comprising an undercoat layer and a photosensitive layer sequentially on a conductive substrate.
- the photosensitive layer contains at least a phthalocyanine compound as a charge generation material, and a polyvinyl acetal resin composed of a repeating unit represented by the following general formula (1) as a resin binder.
- the undercoat layer preferably contains a polyamide resin.
- the photosensitive layer is a laminated type including a charge generation layer and a charge transport layer, and a vinyl chloride copolymer resin is used as a resin binder of the charge generation layer in the charge generation layer.
- the content is preferably 1 to 5% by mass based on the total amount of the resin binder.
- the method for producing an electrophotographic photoreceptor of the present invention includes a process for producing a photosensitive layer by applying a coating solution on a conductive substrate,
- the coating solution contains at least a phthalocyanine compound as a charge generation material, and a polyvinyl acetal resin composed of a repeating unit represented by the following general formula (1) as a resin binder.
- the electrophotographic apparatus of the present invention is characterized in that the photoconductor of the present invention is mounted.
- the above configuration makes it possible to realize an electrophotographic photoreceptor having high transfer resistance, high memory characteristics, and good electrical characteristics, a manufacturing method thereof, and an electrophotographic apparatus.
- FIG. 2 is a schematic cross-sectional view illustrating a configuration example of a negatively charged function separation laminated electrophotographic photoreceptor as an example of the electrophotographic photoreceptor of the present invention.
- 1 is a schematic configuration diagram illustrating an example of an electrophotographic apparatus according to the present invention.
- 2 is an NMR spectrum chart of a resin represented by formula (I-1) according to Example 1. It is a schematic explanatory drawing which shows the printer used for evaluation of the transfer tolerance in an Example.
- the electrophotographic photosensitive member includes a negatively charged laminated type photosensitive member, a positively charged single layered type photosensitive member, and a positively charged laminated type photosensitive member.
- FIG. 1 is a schematic cross-sectional view of a photoconductor for use. As shown in the figure, in the negatively charged laminated type photoreceptor, an undercoat layer 2, a charge generation layer 4 having a charge generation function, and a charge transport layer 5 having a charge transport function are formed on a conductive substrate 1. The photosensitive layers 3 are sequentially laminated. In any type of photoreceptor, a surface protective layer 6 may be further provided on the photosensitive layer 3.
- the conductive substrate 1 serves as one electrode of the photoconductor and also serves as a support for each layer constituting the photoconductor, and may have any shape such as a cylindrical shape, a plate shape, or a film shape.
- a material of the conductive substrate 1 in addition to metals such as aluminum, stainless steel and nickel, the surface of glass or resin may be subjected to a conductive treatment.
- the undercoat layer 2 is generally composed of a resin-based layer or a metal oxide film such as alumite, for controlling the charge injection property from the conductive substrate to the photosensitive layer, or for defects on the substrate surface. It is provided as necessary for the purpose of covering or improving the adhesion between the photosensitive layer and the substrate.
- the resin used for the undercoat layer include acrylic resin, vinyl acetate resin, polyvinyl formal resin, polyurethane resin, polyamide resin, polyester resin, epoxy resin, melamine resin, polyvinyl butyral resin, polyvinyl acetal resin, vinyl phenol resin, and the like. These resins can be used alone or in combination as appropriate.
- the undercoat layer 2 contains a polyamide resin, superiority in transfer resistance is observed.
- the undercoat layer 2 can contain titanium oxide, tin oxide, zinc oxide, copper oxide and the like as metal oxide fine particles. These include a siloxane compound, an alkoxysilane compound, and a silane coupling.
- the surface treatment may be performed with an organic compound such as an agent.
- the charge generation layer 4 is formed by a method such as applying a coating solution in which particles of a charge generation material are dispersed in a resin binder, and receives light to generate charges. Further, at the same time as the charge generation efficiency is high, the injection property of the generated charges into the charge transport layer 5 is important, the electric field dependency is small, and it is desirable that the injection is good even at low electric fields.
- R is any one of a hydrogen atom, a methyl group, an ethyl group, and a propyl group
- the charge generation layer 4 contains the specific resin binder. Thereby, as described later, the desired effect of the present invention can be obtained in combination with the photosensitive layer 3 containing at least a phthalocyanine compound as a charge generating material.
- R in the general formula (1) is a propyl group as a resin binder.
- the degree of acetalization (x + z) is 100 mol%.
- the amount is preferably 86 to 95 mol%.
- the molar ratio x: z of the structural unit in the general formula (1) needs to satisfy the range of 95 to 50: 5 to 50, and more preferably 70 to 50:30 to 50. By setting the range, the transfer resistance is improved.
- the resin binder represented by the general formula (1) is indispensable to use as the resin binder of the charge generation layer 4.
- Polyvinyl acetate is used as a raw material for polyvinyl alcohol, which is a raw material for such a resin binder, but when synthesizing polyvinyl alcohol, the synthesized polyvinyl alcohol generally contains trace amounts of acetyl groups to a few percent. It may remain in the repeating unit, which may remain in the resin binder.
- the case where the resin binder contains an optional component derived from such a raw material is included, and even if such a small amount of acetyl group is present in the repeating unit of the resin binder, Does not affect the effect and properties.
- polycarbonate resin in addition to the resin binder, polycarbonate resin, polyester resin, polyamide resin, polyurethane resin, vinyl chloride resin, vinyl acetate resin, phenoxy resin, polystyrene resin
- Polysulfone resin, diallyl phthalate resin, methacrylic ester resin polymer and copolymer can be used in appropriate combination.
- the content thereof is 10 to 90% by mass, preferably 40 to 60% by mass with respect to the solid content in the charge generation layer 4
- a vinyl chloride copolymer resin is contained as a resin binder in an amount of 1 to 5% by mass with respect to the total amount of the resin binder in the charge generation layer, liquid stability is superior, which is preferable.
- the charge generation layer 4 contains at least a phthalocyanine compound as a charge generation material.
- phthalocyanine compounds various known metal phthalocyanines can be used, among which oxotitanyl phthalocyanine is preferable, ⁇ -type oxotitanyl phthalocyanine, ⁇ -type oxotitanyl phthalocyanine, amorphous oxotitanyl phthalocyanine, particularly Y-type oxotitanyl.
- phthalocyanine or oxo titanyl phthalocyanine having a maximum peak of Bragg angle 2 ⁇ of 9.6 ° in the CuK ⁇ : X-ray diffraction spectrum described in JP-A-8-209023 or US Pat. No. 5,874,570 is used, the sensitivity And significantly improved effects in terms of image quality and transfer resistance.
- the above-mentioned different crystalline oxotitanyl phthalocyanine can be used together, and together with the phthalocyanine compound, other charge generation materials such as various azo pigments, anthanthrone pigments, thiapyrylium pigments, perylene pigments, perinone pigments, A squarylium pigment, a quinacridone pigment, etc. can also be used together.
- the film thickness is determined by the light absorption coefficient of the charge generation material, and is generally 1 ⁇ m or less, preferably 0.5 ⁇ m or less.
- the content of the charge generation material is 10 to 90 mass%, preferably 40 to 60 mass%, based on the solid content in the charge generation layer 4.
- the charge generation layer can also be used with a charge generation material as a main component and a charge transport material or the like added thereto.
- the charge transport layer 5 is mainly composed of a charge transport material and a resin binder.
- the charge transport material various hydrazone compounds, styryl compounds, diamine compounds, butadiene compounds, indole compounds, and the like can be used alone or in combination as appropriate.
- the resin binder polycarbonate resin such as bisphenol A type, bisphenol Z type, bisphenol A type-biphenyl copolymer, polystyrene resin, polyphenylene resin, etc. may be used alone or in appropriate combination. it can.
- the amount of these compounds used is 2 to 50 parts by weight, preferably 3 to 30 parts by weight, based on 100 parts by weight of the resin binder.
- the thickness of the charge transport layer is preferably in the range of 3 to 50 ⁇ m, more preferably 15 to 40 ⁇ m, in order to maintain a practically effective surface potential.
- charge transport materials II-1 to II-5 used in the present invention are shown below, but the present invention is not limited thereto.
- the undercoat layer 2, the charge generation layer 4 and the charge transport layer 5 have high durability including improved sensitivity, decreased residual potential, improved environmental resistance and stability against harmful light, and friction resistance.
- Various additives can be used as needed for the purpose of improving the property. Additives include succinic anhydride, maleic anhydride, dibromosuccinic anhydride, pyromellitic anhydride, pyromellitic acid, trimellitic acid, trimellitic anhydride, phthalimide, 4-nitrophthalimide, tetracyanoethylene, tetracyanoquino Compounds such as dimethane, chloranil, bromanyl, o-nitrobenzoic acid and trinitrofluorenone can be used.
- an antioxidant or a light stabilizer can be added to each of these layers.
- Compounds used for such purposes include chromal derivatives such as tocopherol and ether compounds, ester compounds, polyarylalkane compounds, hydroquinone derivatives, diether compounds, benzophenone derivatives, benzotriazole derivatives, thioether compounds, phenylenediamine derivatives, phosphonic acids Examples include, but are not limited to, esters, phosphites, phenol compounds, hindered phenol compounds, linear amine compounds, cyclic amine compounds, hindered amine compounds, and the like.
- the photosensitive layer 3 may contain a leveling agent such as silicone oil or fluorine-based oil for the purpose of improving the leveling property of the formed film and imparting further lubricity.
- a leveling agent such as silicone oil or fluorine-based oil for the purpose of improving the leveling property of the formed film and imparting further lubricity.
- a surface protective layer 6 may be further provided on the surface of the photosensitive layer 3 as necessary for the purpose of further improving the environmental resistance and mechanical strength.
- the surface protective layer 6 is preferably made of a material having excellent durability against mechanical stress and environmental resistance, and has a capability of transmitting light sensitive to the charge generation layer with as low loss as possible.
- the surface protective layer 6 is composed of a layer mainly composed of a resin binder or an inorganic thin film such as amorphous carbon.
- resin binders silicon oxide (silica), titanium oxide, zinc oxide, calcium oxide, aluminum oxide (alumina), zirconium oxide are used for the purpose of improving conductivity, reducing friction coefficient, and imparting lubricity.
- Metal oxides such as barium sulfate and calcium sulfate, metal nitrides such as silicon nitride and aluminum nitride, fine particles of metal oxide, or fluororesins such as tetrafluoroethylene resin, fluorine comb type You may contain particles, such as graft polymerization resin.
- the surface protective layer 6 contains a charge transport material and an electron acceptor used in the photosensitive layer, and improves the leveling property of the formed film and imparts lubricity.
- a leveling agent such as silicone oil or fluorine-based oil may be contained.
- the film thickness of the surface protective layer 6 itself depends on the blending composition of the protective layer, but can be arbitrarily set within a range that does not adversely affect the residual potential when repeatedly used continuously. it can.
- the method for producing an electrophotographic photoreceptor of the present invention comprises a repeating process represented by the above general formula (1) as a coating solution on a conductive substrate, containing at least a phthalocyanine compound as a charge generation material and a resin binder. What is necessary is just to include the process of apply
- various coating methods such as a dip coating method or a spray coating method can be applied to the coating solution, and the coating solution is not limited to any one of the coating methods.
- the electrophotographic photoreceptor of the present invention can obtain the above-described effects when applied to various machine processes. Specifically, a charging process such as a contact charging method using a roller or a brush, a non-contact charging method using a corotron or scorotron, and a developing method such as a non-magnetic one component, a magnetic one component, or a two component are used. A sufficient effect can be obtained even in development processes such as the contact development and non-contact development methods.
- FIG. 2 shows a schematic configuration diagram of an electrophotographic apparatus according to the present invention.
- the illustrated electrophotographic apparatus 60 includes the electrophotographic photoreceptor 7 of the present invention including the conductive substrate 1, the undercoat layer 2 coated on the outer peripheral surface thereof, and the photosensitive layer 300. Further, the electrophotographic apparatus 60 includes a roller charging member 21, a high-voltage power source 22 that supplies an applied voltage to the roller charging member 21, an image exposure member 23, and a developing device, which are disposed on the outer peripheral edge of the photoreceptor 7.
- a developing device 24 having a roller 241, a paper feeding member 25 having a paper feeding roller 251 and a paper feeding guide 252, a transfer charger (direct charging type) 26, and a cleaning device 27 having a cleaning blade 271; It is also possible to provide a color printer.
- Example 1 As a material for the undercoat layer, 100 parts by mass of the polyamide resin described in Example 1 of JP 2007-178660 A or US Pat. No. 773000 is dissolved in a mixed solvent composed of 1500 parts by mass of methanol and 500 parts by mass of butanol. Then, a slurry was prepared by adding 400 parts by mass of titanium oxide obtained by treating fine particle titanium oxide JMT150 manufactured by Teika Co. with a 1/1 mixture of an aminosilane coupling agent and an isobutylsilane coupling agent.
- the treatment for 20 passes was performed to obtain an undercoat layer coating solution.
- the undercoat layer was formed on the cylindrical aluminum substrate by dip coating using the undercoat layer coating solution prepared above.
- reaction vessel was set in an ice bath containing 5 kg of ice water, and it was confirmed that the reaction solution temperature was 15 ° C. or lower.
- the precipitated polymer was taken out and transferred to a container containing an appropriate amount of ion-exchanged water to immerse the polymer and cure the polymer.
- the cured polymer was then crushed and dried with hot air. In this way, 334 g of a resin having composition I-1 shown in Table 1 below was obtained.
- 96 parts by mass of dichloromethane was prepared by adding 2 parts by mass of a Y-type oxotitanyl phthalocyanine compound described in JP-A-8-209023 as a charge generation material and 2 parts by mass of a polyvinyl acetal resin having the composition I-1 as a resin binder.
- a disk-type bead mill filled with zirconia beads having a bead diameter of 0.4 mm at a bulk filling rate of 85 v / v% with respect to the vessel capacity 5 L of the slurry mixed in the process, the processing liquid flow rate was 300 mL, the disk peripheral speed was 3 m / Processing for 10 passes was performed at s to prepare a charge generation layer coating solution.
- the post-drying film thickness of the charge generation layer obtained by drying under the conditions of a drying temperature of 80 ° C. and a drying time of 30 min was 0.3 ⁇ m.
- Example 2 A photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-2 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 3 A photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-3 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 4 A photoconductor was prepared in the same manner as in Example 1 except that a resin having the composition I-4 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 5 A photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-5 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 6 A photoconductor was prepared in the same manner as in Example 1 except that the resin having composition I-6 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 7 A photoconductor was prepared in the same manner as in Example 1 except that the resin having composition I-7 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 8 A photoconductor was prepared in the same manner as in Example 1 except that the resin having composition I-8 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 9 A photoconductor was prepared in the same manner as in Example 1 except that a resin having the composition I-9 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 10 A photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-10 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 11 2.5 parts by mass of a styrene resin having a repeating unit containing a hydroxy group represented by the following structural formula (2) (Maruzarinka MH2 manufactured by Maruzen Petrochemical Co., Ltd.) and a melamine resin (Uvan 2021 resin solution manufactured by Mitsui Chemicals, Inc.) 2 0.5 part by mass was dissolved in a solvent consisting of 75 parts by mass of tetrahydrofuran and 15 parts by mass of butanol, and then a slurry was prepared by adding 5 parts by mass of aminosilane-treated titanium oxide fine particles.
- structural formula (2) Maruzarinka MH2 manufactured by Maruzen Petrochemical Co., Ltd.
- a melamine resin Uvan 2021 resin solution manufactured by Mitsui Chemicals, Inc.
- the treatment for 20 passes was performed to obtain an undercoat layer coating solution.
- a photoconductor was prepared in the same manner as in Example 1 except that this coating solution was used as the undercoat layer coating solution.
- Example 12 In the same manner as in Example 1, except that ⁇ -type titanyl phthalocyanine described in JP-A-61-217050 or US Pat. No. 4,728,592 was used as the charge generation material in place of Y-type oxotitanyl phthalocyanine. The body was made.
- Example 13 A photoconductor was prepared in the same manner as in Example 1 except that X-type metal-free phthalocyanine (Fastogen Blue 8120B manufactured by Dainippon Ink & Chemicals, Inc.) was used as the charge generation material instead of Y-type titanyl phthalocyanine. .
- X-type metal-free phthalocyanine Fluorescent Blue 8120B manufactured by Dainippon Ink & Chemicals, Inc.
- Example 14 As in Example 1, except that 5% by mass of vinyl chloride copolymer resin (MR110 manufactured by Nippon Zeon Co., Ltd.) was used as the resin binder of the charge generation layer with respect to the total amount of the resin in the charge generation layer. A photoconductor was prepared.
- MR110 manufactured by Nippon Zeon Co., Ltd.
- Example 15 As in Example 1, except that 1% by mass of vinyl chloride copolymer resin (MR110 manufactured by Nippon Zeon Co., Ltd.) was used as the resin binder of the charge generation layer with respect to the total amount of the resin in the charge generation layer. A photoconductor was prepared.
- MR110 manufactured by Nippon Zeon Co., Ltd.
- Example 16 A photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-11 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 17 A photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-12 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 18 A photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-13 shown in Table 1 below was used as the resin binder for the charge generation layer.
- a photoconductor was prepared in the same manner as in Example 1 except that polyvinyl butyral resin (BM-1 manufactured by Sekisui Chemical Co., Ltd.) was used as the resin binder for the charge generation layer.
- BM-1 polyvinyl butyral resin manufactured by Sekisui Chemical Co., Ltd.
- a photoconductor was prepared in the same manner as in Example 1 except that polyvinyl butyral resin (BM-S manufactured by Sekisui Chemical Co., Ltd.) was used as the resin binder for the charge generation layer.
- BM-S polyvinyl butyral resin manufactured by Sekisui Chemical Co., Ltd.
- Example 3 A photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-14 shown in Table 1 below was used as the resin binder for the charge generation layer.
- a photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-15 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 5 A photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-16 shown in Table 1 below was used as the resin binder for the charge generation layer.
- a photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-17 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 7 A photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-18 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 8 A photoconductor was prepared in the same manner as in Example 1 except that the resin having the composition I-19 shown in Table 1 below was used as the resin binder for the charge generation layer.
- Example 9 A photoconductor was prepared in the same manner as in Example 1 except that a resin having the composition I-20 shown in Table 1 below was used as the resin binder for the charge generation layer.
- L, m, and n in the table represent mol% of each structural unit in the following formula, respectively.
- exposure light split at 780 nm using a filter is irradiated for 5 seconds from the time when the surface potential becomes ⁇ 800 V, and it is necessary to attenuate the light until the surface potential becomes ⁇ 100 V.
- the exposure amount was determined as sensitivity E100 ( ⁇ Jcm ⁇ 2 ).
- the photoconductors obtained in the respective examples and comparative examples are mounted on a monochrome printer ML-2241 (manufactured by Samsung Electronics Co., Ltd.) modified so that the surface potential of the photoconductor can be observed.
- solid white 3 in each environment (LL (low temperature and low humidity): 10 ° C. and 15% RH, NN (normal temperature and humidity): 25 ° C. and 50% RH, HH (high temperature and high humidity): 35 ° C. and 85% RH)
- LL low temperature and low humidity
- NN normal temperature and humidity
- HH high temperature and high humidity
- the post-exposure potential and the image memory after printing one sheet and three solid black sheets were evaluated.
- pass / fail was judged by the potential fluctuation amount (LL to HH) after exposure under each environment.
- the memory phenomenon in which the checker flag is reflected in the halftone part is read in the print evaluation of the image sample with the checker flag pattern in the first half of the scanner sweep and the halftone in the second half.
- A very good
- ⁇ good
- ⁇ thin memory generated
- x dark memory generated
- the amount of change in surface potential during charging before and after printing 10,000 sheets in a normal temperature and humidity environment and the image memory were also evaluated.
- the transfer electrode 10 was applied stepwise from a high voltage power source by constant voltage control at 0 kV (first sheet) and 1.2 kV (second sheet) to 2.2 kV (seventh sheet). This is carried out in each environment (LL (low temperature and low humidity): 10 ° C., 15% RH, NN (room temperature and normal humidity): 25 ° C., 50% RH).
- LL low temperature and low humidity
- NN room temperature and normal humidity
- the dark part potential) ⁇ V7 (seventh dark part potential) was calculated, and the smaller ⁇ V, the better.
- reference numeral 8 denotes a charger
- reference numeral 9 denotes an exposure light source.
- each charge generation layer coating solution prepared in each of the examples and comparative examples was sealed in a transparent glass bottle, at room temperature and humidity (25 ° C., 50% RH). Stored still below. The presence or absence of partial agglomeration, precipitation, separation, etc. in the coating solution was visually observed. Good ( ⁇ : very good, ⁇ : good, almost no separation, agglomeration or sedimentation, ⁇ to ⁇ : A state in which any one of separation, aggregation and sedimentation is observed). These results are shown in the table below.
- a photoconductor that has good initial electrical characteristics, electrical characteristics in use environment fluctuations, memory characteristics, and good transfer resistance It can be seen that Further, it was confirmed that the transfer performance under each environment is stabilized by increasing the degree of acetalization to the range according to the present invention and decreasing the ratio of structural units (y) containing a highly hydrophilic hydroxyl group.
- the difference between the value in the NN environment and the value in the LL environment of the ⁇ V value indicating the transfer resistance is smaller. It can be seen that the environment shows a stable fluctuation trend. Furthermore, the photoreceptor according to the combination with Y-type titanyl phthalocyanine as a charge generation material showed higher sensitivity and higher transfer resistance. Furthermore, the stability of the coating solution was the best when 1 to 5% by mass of vinyl chloride copolymer resin was combined with the total amount of resin in the charge generation layer.
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Abstract
Description
前記感光層が、電荷発生材料として少なくともフタロシアニン化合物を含有し、かつ、樹脂バインダーとして、下記一般式(1)で表される繰返し単位からなるポリビニルアセタール樹脂を含むことを特徴とするものである。
(式(1) 中、Rは水素原子、メチル基、エチル基またはプロピル基のいずれかであり、x,y,zはそれぞれ各構造単位のmol%を示し、x+y+z=100であり、nは1~5の整数であり、アセタール化度(x+z)が76~99mol%であって、かつ、構造単位のモル比(x:z)が95~50:5~50である)
前記塗布液が、電荷発生材料として少なくともフタロシアニン化合物を含有し、かつ、樹脂バインダーとして、下記一般式(1)で表される繰返し単位からなるポリビニルアセタール樹脂を含むことを特徴とするものである。
(式(1) 中、Rは水素原子、メチル基、エチル基またはプロピル基のいずれかであり、x,y,zはそれぞれ各構造単位のmol%を示し、x+y+z=100であり、nは1~5の整数であり、アセタール化度(x+z)が76~99mol%であって、かつ、構造単位のモル比(x:z)が95~50:5~50である)
電子写真用感光体には、負帯電積層型感光体、正帯電単層型感光体、および、正帯電積層型感光体があるが、ここでは一例として、図1に、負帯電積層型電子写真用感光体の模式的断面図を示す。図示するように、負帯電積層型感光体においては、導電性基体1の上に、下引き層2と、電荷発生機能を備えた電荷発生層4および電荷輸送機能を備えた電荷輸送層5からなる感光層3とが、順次積層されている。なお、いずれのタイプの感光体においても、感光層3の上に、さらに表面保護層6を設けてもよい。
(式(1) 中、Rは水素原子、メチル基、エチル基またはプロピル基のいずれかであり、x,y,zはそれぞれ各構造単位のmol%を示し、x+y+z=100であり、nは1~5の整数であり、アセタール化度(x+z)が76~99mol%であって、かつ、構造単位のモル比(x:z)が95~50:5~50である)で表される繰返し単位からなるポリビニルアセタール樹脂を含有させた点が重要であり、構成モノマーとしてフェニル基を含むことが特徴的である。ここで、積層型感光体の場合には、電荷発生層4が上記特定の樹脂バインダーを含有するものとする。これにより、後述するように、感光層3に電荷発生材料として少なくともフタロシアニン化合物を含有させることと併せて、本発明の所期の効果を得ることができる。
[実施例1]
下引き層の材料として、特開2007-178660号公報もしくは米国特許7723000号明細書の実施例1に記載のポリアミド樹脂100質量部を、メタノール1500質量部およびブタノール500質量部からなる混合溶媒に溶解させた後、テイカ社製 微粒子酸化チタンJMT150を、アミノシラン系カップリング剤とイソブチルシラン系カップリング剤との1/1の混合物で処理してなる酸化チタン400質量部を加えたスラリーを作製した。このスラリーにつき、ビーズ径0.3mmのジルコニアビーズをベッセル容量に対して70v/v%の嵩充填率で充填したディスクタイプのビーズミルを用いて、処理液流量400mL、ディスク周速3m/sにて20パス分処理を行い、下引き層塗布液とした。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-2の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-3の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-4の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-5の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-6の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-7の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-8の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-9の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-10の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
下記構造式(2)に示すヒドロキシ基を含む繰返し単位を有するスチレン樹脂(丸善石油化学(株)製 マルカリンカMH2)2.5質量部と、メラミン樹脂(三井化学(株)製 Uvan2021樹脂液)2.5質量部とを、テトラヒドロフラン75質量部およびブタノール15質量部からなる溶媒に溶解させた後、アミノシラン処理された酸化チタン微粒子5質量部を加えたスラリーを作製した。このスラリーにつき、ビーズ径0.3mmのジルコニアビーズをベッセル容量に対して70v/v%の嵩充填率で充填したディスクタイプのビーズミルを用いて、処理液流量400mL、ディスク周速3m/sにて20パス分処理を行い、下引き層塗布液とした。下引き層塗布液として、この塗布液を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生材料として、Y型オキソチタニルフタロシアニンに代えて、特開昭61-217050号公報もしくは米国特許4728592号明細書に記載のα型チタニルフタロシアニンを用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生材料として、Y型チタニルフタロシアニンに代えて、X型無金属フタロシアニン(大日本インキ化学工業(株)製 Fastogen Blue 8120B)を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、電荷発生層中の樹脂全量に対して5質量%の塩化ビニル系共重合樹脂(日本ゼオン(株)製 MR110)を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、電荷発生層中の樹脂全量に対して1質量%の塩化ビニル系共重合樹脂(日本ゼオン(株)製 MR110)を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-11の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-12の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-13の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、ポリビニルブチラール樹脂(積水化学工業(株)製 BM-1)を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、ポリビニルブチラール樹脂(積水化学工業(株)製 BM-S)を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-14の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-15の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-16の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-17の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-18の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-19の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
電荷発生層の樹脂バインダーとして、下記表1中に示す組成I-20の樹脂を用いた以外は実施例1と同様にして、感光体を作製した。
Vk5 =(V5/V0)×100 (i)
これらの結果を、下記の表中に示す。
2 下引き層
3 感光層
4 電荷発生層
5 電荷輸送層
6 保護層
7 電子写真用感光体
8 帯電器
9 露光光源
10 転写極部
21 ローラ帯電部材
22 高圧電源
23 像露光部材
24 現像器
241 現像ローラ
25 給紙部材
251 給紙ローラ
252 給紙ガイド
26 転写帯電器(直接帯電型)
27 クリーニング装置
271 クリーニングブレード
28 除電部材
60 電子写真装置
300 感光層
Claims (7)
- 前記樹脂バインダーとして、前記一般式(1)中のRがプロピル基であるポリビニルブチラール樹脂を用いる請求項1記載の電子写真用感光体。
- 前記フタロシアニン化合物が、Y型オキソチタニルフタロシアニンである請求項1記載の電子写真用感光体。
- 前記下引き層がポリアミド樹脂を含有する請求項1記載の電子写真用感光体。
- 前記感光層が電荷発生層と電荷輸送層とを含む積層型であり、かつ、該電荷発生層の樹脂バインダーとして、塩化ビニル系共重合樹脂を、該電荷発生層中の樹脂バインダーの全量に対して1~5質量%にて含有する請求項1記載の電子写真用感光体。
- 導電性基体上に、塗布液を塗布して感光層を形成する工程を包含する電子写真用感光体の製造方法において、
前記塗布液が、電荷発生材料として少なくともフタロシアニン化合物を含有し、かつ、樹脂バインダーとして、下記一般式(1)で表される繰返し単位からなるポリビニルアセタール樹脂を含むことを特徴とする電子写真用感光体の製造方法。
(式(1) 中、Rは水素原子、メチル基、エチル基またはプロピル基のいずれかであり、x,y,zはそれぞれ各構造単位のmol%を示し、x+y+z=100であり、nは1~5の整数であり、アセタール化度(x+z)が76~99mol%であって、かつ、構造単位のモル比(x:z)が95~50:5~50である) - 請求項1記載の電子写真用感光体が搭載されていることを特徴とする電子写真装置。
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KR100644610B1 (ko) * | 2004-02-11 | 2006-11-10 | 삼성전자주식회사 | 전기적 및 기계적 특성이 우수한 전자사진 감광체 및 이를채용한 전자사진 화상형성장치 |
JP2006133701A (ja) | 2004-11-09 | 2006-05-25 | Kyocera Mita Corp | 積層型電子写真感光体 |
WO2007066790A2 (en) * | 2005-12-07 | 2007-06-14 | Canon Kabushiki Kaisha | Polyvinyl acetal resin, electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
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- 2011-02-15 WO PCT/JP2011/053186 patent/WO2012111099A1/ja active Application Filing
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2012
- 2012-02-14 TW TW101104713A patent/TWI545410B/zh not_active IP Right Cessation
- 2012-02-14 WO PCT/JP2012/053410 patent/WO2012111672A1/ja active Application Filing
- 2012-02-14 KR KR1020137021120A patent/KR101806277B1/ko active IP Right Grant
- 2012-02-14 CN CN201280008707.6A patent/CN103384851B/zh not_active Expired - Fee Related
- 2012-02-14 US US13/985,037 patent/US9081313B2/en not_active Expired - Fee Related
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JPS6295537A (ja) * | 1985-10-23 | 1987-05-02 | Mitsubishi Chem Ind Ltd | 電子写真用感光体 |
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Also Published As
Publication number | Publication date |
---|---|
CN103384851B (zh) | 2016-08-10 |
WO2012111099A1 (ja) | 2012-08-23 |
KR20140021541A (ko) | 2014-02-20 |
US20130316276A1 (en) | 2013-11-28 |
CN103384851A (zh) | 2013-11-06 |
US9081313B2 (en) | 2015-07-14 |
KR101806277B1 (ko) | 2017-12-07 |
TWI545410B (zh) | 2016-08-11 |
TW201250412A (en) | 2012-12-16 |
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