LT4555B - The organic electrophotographic photoreceptor for liquid development and process for preparing thereof - Google Patents
The organic electrophotographic photoreceptor for liquid development and process for preparing thereof Download PDFInfo
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- LT4555B LT4555B LT97-159A LT97159A LT4555B LT 4555 B LT4555 B LT 4555B LT 97159 A LT97159 A LT 97159A LT 4555 B LT4555 B LT 4555B
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- Lithuania
- Prior art keywords
- electrophotographic photoreceptor
- organic electrophotographic
- electrically conductive
- photosensitive coating
- conductive substrate
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- 108091008695 photoreceptors Proteins 0.000 title claims abstract description 27
- 239000007788 liquid Substances 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000000463 material Substances 0.000 claims abstract description 10
- 230000004888 barrier function Effects 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 21
- 239000011248 coating agent Substances 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 10
- 239000012876 carrier material Substances 0.000 claims description 7
- 239000002356 single layer Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- -1 toluene hydrazones Chemical class 0.000 abstract description 16
- 239000002800 charge carrier Substances 0.000 abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 150000007857 hydrazones Chemical class 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- UXUFTKZYJYGMGO-CMCWBKRRSA-N (2s,3s,4r,5r)-5-[6-amino-2-[2-[4-[3-(2-aminoethylamino)-3-oxopropyl]phenyl]ethylamino]purin-9-yl]-n-ethyl-3,4-dihydroxyoxolane-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(NCCC=3C=CC(CCC(=O)NCCN)=CC=3)=NC(N)=C2N=C1 UXUFTKZYJYGMGO-CMCWBKRRSA-N 0.000 description 3
- YGBCLRRWZQSURU-UHFFFAOYSA-N 4-[(diphenylhydrazinylidene)methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 YGBCLRRWZQSURU-UHFFFAOYSA-N 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HDOZLDYBGNJMMZ-UHFFFAOYSA-N 4-(dipropylamino)benzaldehyde Chemical compound CCCN(CCC)C1=CC=C(C=O)C=C1 HDOZLDYBGNJMMZ-UHFFFAOYSA-N 0.000 description 2
- BQGMKJXBIIUCMW-UHFFFAOYSA-N C(C1=CC=CC=C1)CNC1=CC=C(C=O)C=C1 Chemical compound C(C1=CC=CC=C1)CNC1=CC=C(C=O)C=C1 BQGMKJXBIIUCMW-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005597 hydrazone group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- NRESDXFFSNBDGP-UHFFFAOYSA-N (4-bromophenyl)hydrazine Chemical compound NNC1=CC=C(Br)C=C1 NRESDXFFSNBDGP-UHFFFAOYSA-N 0.000 description 1
- XAMBIJWZVIZZOG-UHFFFAOYSA-N (4-methylphenyl)hydrazine Chemical compound CC1=CC=C(NN)C=C1 XAMBIJWZVIZZOG-UHFFFAOYSA-N 0.000 description 1
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 1
- CNPVJWYWYZMPDS-UHFFFAOYSA-N 2-methyldecane Chemical compound CCCCCCCCC(C)C CNPVJWYWYZMPDS-UHFFFAOYSA-N 0.000 description 1
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 description 1
- LNYTUARMNSFFBE-UHFFFAOYSA-N 4-(diethylazaniumyl)benzoate Chemical compound CCN(CC)C1=CC=C(C(O)=O)C=C1 LNYTUARMNSFFBE-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HKPALTUQHDUVQB-UHFFFAOYSA-N n-benzyl-n-(benzylideneamino)-4-methylaniline Chemical compound C1=CC(C)=CC=C1N(N=CC=1C=CC=CC=1)CC1=CC=CC=C1 HKPALTUQHDUVQB-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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- Photoreceptors In Electrophotography (AREA)
Abstract
Description
Išradimas priskiriamas organiniams elektrofotografiniams totoreceptoriams, kurie naudojami elektrofotografiniuose aparatuose (kopijavimo aparatuose, lazeriniuose spausdintuvuose ir kt.), dirbančiuose su skystais ryškalais. Organinis elektrofotografinis fotoreceptorius, skirtas darbui su skystais ryškalais, turintis fotojautrią dangą, gali būti taikomas darbui su monosluoksne arba daugiasluoksne fotojautria danga, kuri gali turėti tiek neigiamai, tiek teigiamai įelektrintą paviršių.BACKGROUND OF THE INVENTION The invention relates to organic electrophotographic totoreceptors used in electrophotographic apparatus (photocopiers, laser printers, etc.) working with liquid developers. An organic electrophotographic photoreceptor for use with a liquid developer having a photosensitive coating can be applied to a monolayer or multilayer photosensitive coating that can have both a negatively and positively electrified surface.
Šiuo metu technikoje naudojami organiniai elektrofotografiniai fotoreceptoriai, sudaryti iš kelių sluoksnių, užneštų ant elektrai laidaus pagrindo.Currently, the technique utilizes organic electrophotographic photoreceptors consisting of several layers deposited on an electrically conductive substrate.
Svarbi organinių elektrofotografinių fotoreceptorių dalis - fotojautri danga. Danga gali būti monosluoksne, kur vyksta krūvininkų nešėjų generacija ir jų transportas, arba kelių sluoksnių danga, turinti atskiras funkcijas atliekančius generacinj ir transportinį sluoksnius. Fotojautrūs pigmentai, pvz.: azopigmentai, ftalocianino pigmentai, jų mišiniai, naudojami kaip generacinės medžiagos. Krūvininkus transportuojančios medžiagos dažniausiai yra mažos molekulinės masės, pvz.: pirazolino (JP - B N.4188/1977), hidrazono (JP - B N.42380/1980, JP - A N.52063/1980), trifenilamino (JP - A N. 114058/1991, JP -A N.53349/1993), stilbeno (JP - A N.151955/1979, JP - A N. 198043/1983) ir kiti junginiai. Rišamųjų medžiagų funkcijas atlieka įvairūs polimerai, pvz.: polikarbonatai, polieterinės dervos, poliarilatai ir kt. Fotojautri danga turi ir kitus priedus: stabilizatorius, dispergatorius, antioksidatorius ir kt.An important part of organic electrophotographic photoreceptors is the photosensitive coating. The coating may be in a monolayer for carrier generation and transport, or as a multi-layer coating having separate functions for generating and transporting layers. Photosensitive pigments, eg: azopigments, phthalocyanine pigments, mixtures thereof, used as generating agents. Charger transporting agents are generally low molecular weight, e.g., pyrazoline (JP - B N.4188 / 1977), hydrazone (JP - B N.42380 / 1980, JP - A N.52063 / 1980), triphenylamine (JP - A N. 114058/1991, JP-A N.53349 / 1993), stilbene (JP-A N.151955 / 1979, JP-A N. 198043/1983) and other compounds. Binders act as various polymers, for example polycarbonates, polyether resins, polyarylates, etc. The photosensitive coating also has other additives: stabilizers, dispersants, antioxidants and more.
Organinis elektrofotografinis fotoreceptorius gaminamas įvairiais būdais (purškimu, liejimu su filjere, panardinimu ir kt.), užnešant ant elektrai laidaus pagrindo reikiamų medžiagų tirpalus arba dispersijas.Organic electrophotographic photoreceptors are produced in a variety of ways (spraying, filler casting, dipping, etc.) by applying solutions or dispersions of the required materials to an electrically conductive substrate.
Elektrai laidus pagrindas daromas iš aliuminio, jo lydinių ar kitų metalų (vario, nikelio ar kt.) arba iš izoliatoriaus (polieterinė pievelė, popierius ar kt.), kuris yra padengtas laidžių sluoksniu iš aliuminio, vario, paladžio, titano oksido, indžio oksido ar kt. Ant elektrai laidaus pagrindo užnešamas barjerinis sluoksnis, kuris gali būti sudarytas iš kazeino, želatinos, poliamido, poli (vinilo alkoholio) ar kitos tam tikslui tinkamos medžiagos.The electrically conductive substrate is made of aluminum, its alloys or other metals (copper, nickel, etc.) or an insulator (polyether patch, paper, etc.) which is coated with a conductive layer of aluminum, copper, palladium, titanium oxide, indium oxide or whatever. A barrier layer may be applied to the electrically conductive substrate, which may consist of casein, gelatin, polyamide, poly (vinyl alcohol) or other suitable material.
Priklausomai nuo kopijavimo aparato, vaizdui gauti naudojami arba skysti arba miltelių pavidalo ryškalai. Paskutiniuoju metu plačiai pradėti naudoti skysti ryškalai, leidžiantys gauti vaizdą su labai aukšta skiriamąja galia. Nežiūrint į esamą didelę skystų ryškalų, naudojamų elektrofotografijoje įvairovę, visi jie turi vieną bendrą ingredientą, būtent, nepolinj skystį su tam tikromis savybėmis: žemu elektros laidumu, mažu toksiškumu, mažu tirpumu, neturinčiu kvapo ir kt. Tai gali būti šakoti alifatiniai angliavandeniliai, būtent, Izopar-G, Izopar-H, Izopar-K, Izopar-L, Izopar-M, Izopar-V arba normalūs parafininiai skysčiai: Norpar 12, Norpar 13, Norpar 15 (Εχχοη Corporation). Visi šie angliavandeniliai yra švarūs ir turi tam tikrą virimo temperatūrą Tvir, pvz.: Izopar-G TVir= 157°-176° C; Izopar-K Tvir= 177°-197° C; Izopar-L Tvir= 188°-206° ir t.t. (USPat 5492788).Depending on the copier, either liquid or powder forms are used to obtain the image. Recently, liquid developers have been widely used to provide very high resolution images. Despite the large variety of liquid brighteners used in electrophotography, they all have one common ingredient, namely non-polar liquid with certain properties: low electrical conductivity, low toxicity, low solubility, odor-free, and so on. These may be branched aliphatic hydrocarbons, namely, Isopar-G, Izopar-H, Izopar-K, Izopar-L, Izopar-M, Izopar-V, or normal paraffinic liquids: Norpar 12, Norpar 13, Norpar 15 (Εχχοη Corporation). All of these hydrocarbons are clean and have a boiling temperature of T top, such Izopar .: G V T r = 157 ° -176 ° C; Isopar-K T vir = 177 ° -197 ° C; Isopar-L T vir = 188 ° -206 °, etc. (USPat 5492788).
Organinį elektrofotografinį fotoreceptorių veikiant parafininiais angliavandeniliais, gali atsirasti neigiami reiškiniai, pvz., krūvininkus transportuojančios medžiagos ekstrakcija iš sluoksnio, tirpimas, sluoksnio susiskaidymas ir kt. Dėl to krūvininkus transportuojančios medžiagos duomenys blogėja.Exposure to organic electrophotographic photoreceptors with paraffinic hydrocarbons may result in adverse events such as layer extraction, dissolution, layer fragmentation, and more. As a result, the data on the material transporting the stackers deteriorates.
Europos patente EP 0767411 A1 (G03G5/05) siūlomas fotoreceptorius, stabiliai dirbantis su skystu ryškalu bei turintis specialų polikarbonato polimerą, ir aukštą stiklėjimo temperatūrą. Kaip krūvininkus transportuojančios medžiagos siūlomi hidrazonai, kurių bendra formulė:European Patent EP 0767411 A1 (G03G5 / 05) proposes a photoreceptor that is stable in liquid development and has a special polycarbonate polymer and a high glass transition temperature. Hydrazones are proposed as bulk carriers as follows:
kur R1, R6, R9 - vandenilis arba alkilas; R3, R4 - alkilas arba arilas. Europos patente EP 0754977 A1 (G03G5/06, G03G5/05) siūlomas fotoreceptorius, stabiliai dirbantis su skystuoju ryškalu, turintis krūvininkus transportuojančią medžiagą - hidrazoną, kurio bendra formulė:wherein R 1 , R 6 , R 9 are hydrogen or alkyl; R 3 , R 4 are alkyl or aryl. European Patent EP 0754977 A1 (G03G5 / 06, G03G5 / 05) proposes a photoreceptor, which is stable in liquid development and contains a carrier material, hydrazone, of the general formula:
R2 (<O>-ch^nR1 R 2 (<O> -ch ^ n R 1
O>-CH= N-N<O> -CH = N-N <
kur R1,R2,R8,R9 -vandenilis arba arilas.wherein R 1 , R 2 , R 8 , R 9 are hydrogen or aryl.
Europos patente EP 0618507 A1 (G03G5/06, G03G5/05) siūlomas fotoreceptorius, stabiliai dirbantis su skystuoju ryškalu (Izoparo -L pagrindu, Esso Sekiju K.K. gamyba), kurio krūvininkus transportuojančios medžiagos stiklėjimo temperatūra ne mažesnė kaip 50° C ir silpnai tirpsta toluene (mažiau nei 13 %, esant 25° C temperatūrai). Tarp krūvininkus transportuojančių medžiagų siūlomi: hidrazonas, aromatiniai aminai, stilbeno junginiai ir kt.European Patent EP 0618507 A1 (G03G5 / 06, G03G5 / 05) proposes a photoreceptor stable in liquid developer (Isopar -L-based, Esso Sekiju KK production), having a charge carrier material with a glass transition temperature of at least 50 ° C and poorly soluble in toluene. (less than 13% at 25 ° C). Among the materials that transport the carriers are hydrazone, aromatic amines, stilbene compounds and others.
Norint gauti stabiliai dirbantį su skystaisiais ryškalais organinį elektrofotografinj, su fotojautria danga, fotoreceptorių, siūloma krūvininkus transportuojančią medžiagą fotojautrioje dangoje naudoti hidrazono junginius, papildomai perkristalintus iš tolueno. Papildomas medžiagos apdorojimas leidžia suvienodinti krūvininkus transportuojančių medžiagų savybes, skirtas kontaktiniam darbui su skystuoju ryškalu, nežiūrint j jų struktūrinę formulę.In order to obtain a stable photoelectric organic photoelectric organic photoelectric receptor, it is proposed to use hydrazone compounds additionally recrystallized from toluene in the photosensitive coating of the carrier material. The additional material treatment enables the properties of the carrier materials to be uniformed for contact with the liquid developer, regardless of their structural formula.
Šio išradimo tikslas - organinio elektrofotografinio fotoreceptoriaus, pasižyminčio geromis elektrofotografinėmis savybėmis bei stabiliai, be parametrų nukrypimų, dirbančio su skystuoju ryškalu, gavimas. Tam tikslui siūloma organinio elektrofotografinio fotoreceptoriaus, susidedančio iš elektrai laidaus pagrindo, barjerinio sluoksnio ir fotojautrios dangos, fotojautrioje dangoje krūvininkus transportuojančią medžiagą imti iš perkristalintų iš tolueno hidrazonų, kurių bendra formulė:The object of the present invention is to provide an organic electrophotographic photoreceptor having good electrophotographic properties and stable, non-parametric deviation working with a liquid developer. For this purpose, it is proposed that the charge transport material of an organic electrophotographic photoreceptor consisting of an electrically conductive substrate, a barrier layer and a photosensitive coating be recrystallized from toluene hydrazones having the following general formula:
R2 kur A - substituota arilo grupė; 9-alkilkarbazol-3-ilo radikalas.R 2 wherein A is a substituted aryl group; 9-alkylcarbazol-3-yl radical.
Ri - vandenilio atomas, halogenas, alkilo grupė.Ri is a hydrogen atom, a halogen, an alkyl group.
R2 - alkilo, arilo, alkilarilo grupė.R 2 is an alkyl, aryl, alkylaryl group.
n=0 arba 1.n = 0 or 1.
Siūlomas organinis elektrofotografinis fotoreceptorius gaminamas taip: ant elektrai laidaus pagrindo užnešamas barjerinis sluoksnis, o prieš padengiant fotojautria danga, krūvininkus transportuojanti medžiaga papildomai perkristalinama iš tolueno.The proposed organic electrophotographic photoreceptor is fabricated as follows: a barrier layer is applied to the electrically conductive substrate and the carrier material is further recrystallized from toluene before being coated with a photosensitive coating.
pavyzdysexample
Ant 30 mm skersmens ir 254 mm ilgio aliumininių cilindrų su barjeriniu 0,5 pm storio poliamido 6/66/ 610 sluoksniu, užnešama fotojautri danga iš generacinio titanilo ftalocianino sluoksnio, kurio storis 0.1 μιτι, bei transportinio sluoksnio, gauto panardinant cilindrą į tirpalą, kurj sudaro 50 svorio dalių polikarbonato (APEC 9202), 50 svorio dalių 4LT 4555 B feniletilaminobenzaldehido 1-benzil-1-fenilhidrazono ir 200 svorio dalių dichlormetano.Aluminum cylinders 30 mm in diameter and 254 mm long with a barrier layer of 0.5 µm polyamide 6/66/610, coated with a photosensitive coating of 0.1 µιτι generic titanyl phthalocyanine layer and a transport layer obtained by immersion of the cylinder in a solution. Contains 50 parts by weight of polycarbonate (APEC 9202), 50 parts by weight of 4LT 4555 B phenylethylaminobenzaldehyde 1-benzyl-1-phenylhydrazone and 200 parts by weight dichloromethane.
Išdžiovinus, gautas 25 pm storio transportinis sluoksnis.After drying, a 25 µm transport layer was obtained.
4-Feniletilaminobenzaldehido 1 -benzil-1 -fenilhidrazonas gaunamas:4-Phenylethylaminobenzaldehyde 1-benzyl-1-phenylhydrazone is obtained from:
100 g 4-feniletilaminobenzaldehido 1 -benzil-1 -fenilhidrazono (lydymosi temperatūra - 120,5° - 122° C), gauto alkilarilinant100 g of 4-phenylethylaminobenzaldehyde 1-benzyl-1-phenylhydrazone (m.p. 120.5 ° -122 ° C) obtained by alkylarylation
4-feniletilaminobenzaldehido ir fenilhidrazino kondensacijos produktą benzilchloridu, ištirpinama 250 ml tolueno. Tirpalas, pridėjus 3 g aktyvintos anglies, intensyviai maišant pavirinamas ir nufiltruojamas. Filtratas paliekamas stovėti kambario temperatūroje (25° C). Po 6 h iškritęThe condensation product of 4-phenylethylaminobenzaldehyde and phenylhydrazine with benzyl chloride is dissolved in 250 ml of toluene. The solution, after addition of 3 g of activated carbon, is boiled under vigorous stirring and filtered. Leave the filtrate to stand at room temperature (25 ° C). After 6 h fall out
4-feniletilaminobenzaldehido 1-benzil-1-fenilhidrazono kristalai nufiltruojami, perplaunami atšaldytu toluenu (5° C), etanoliu ir džiovinami - 50°-60°C temperatūroje. Gaunama 87 g paruošto krūvininkus transportuojančio junginio.The crystals of 4-phenylethylaminobenzaldehyde 1-benzyl-1-phenylhydrazone are filtered off, washed with chilled toluene (5 ° C), ethanol and dried at -50 ° -60 ° C. 87 g of the prepared charge carrier compound are obtained.
Gautas organinis elektrofotografinis fotoreceptorius buvo išbandytas matavimo stende, kur nustatyta: pradinis potencialas Uo, potencialo pusiau kritimo laikas tamsoje t1/2, fotojautris S, liekamasis potencialas lUk.·The resulting organic electrophotographic photoreceptor was tested on a measuring bench for the following: initial potential U o , half-life potential in the dark t 1/2 , photosensitive S, residual potential lUk ·
Po to organinis elektrofotografinis fotoreceptorius savaitę 25° C temperatūroje išlaikomas indelyje su Izoparu-L. Ištraukus iš Izoparo-L, organinis elektrofotografinis fotoreceptorius 1 h laikomas tamsoje, o po to pakartojami matavimai. Gauti elektrofotografiniai duomenys pateikti lentelėje.The organic electrophotographic photoreceptor is then maintained for one week at 25 ° C in a dish containing Isopar-L. After extraction from Isopar-L, the organic electrophotographic photoreceptor was kept in the dark for 1 h and then the measurements were repeated. The electrophotographic data obtained are shown in the table.
pavyzdysexample
Ant polietilentereftalatinės plėvelės su 90 pm storio elektrai laidžių sluoksniu iš titano oksido ir barjerinio 0,5 pm kazeino sluoksnio, užnešama fotojautri danga, susidedanti iš 0,2 pm storio fluorenono eilės bisazopigmento generacinio sluoksnio bei transportinio sluoksnio, kurį sudaro 55 svorio dalys polikarbonato (APEC 9202), 45 svorio dalys 4-dietilaminobenzaldehido 1,1difenilhidrazono ir 200 svorio dalių dichlormetano.Polyethylene terephthalate film with a 90 µm thick electrically conductive layer of titanium oxide and a barrier layer of 0.5 µm casein, which is a photosensitive coating consisting of a 0.2 µm fluorenone bisazo pigment generating layer and a transport layer consisting of 55 parts by weight of polycarbonate (APEC) 9202), 45 parts by weight of 4-diethylaminobenzaldehyde 1,1-diphenylhydrazone and 200 parts by weight of dichloromethane.
Išdžiovinus, gautas 28 pm storio transportinis sluoksnis.Upon drying, a 28 µm transport layer was obtained.
4-Dietilaminobenzaidehido 1,1-difenilhidrazonas gaunamas:4-Diethylaminobenzoate anhydrous 1,1-diphenylhydrazone is obtained by:
100 g 4-dietilaminobenzaldehido 1,1-difenilhidrazono (lydymosi temperatūra93°-94,5° C), gauto kondensuojant 4-dietilaminobenzaldehidą ir N,Ndifenilhidraziną, ištirpinama 175 ml, pridedama 3 g aktyvintos anglies, intensyviai maišant pavirinama ir nufiltruojama. Tirpalas paliekamas stovėti 10°-15° C temperatūroje. Po paros iškritę 4-dietilaminobenzaldehido 1,1difenilhidrazono kristalai nufiltruojami, perplaunami atšaldytu etanoliu (5° C) ir išdžiovinami 40°-45° C temperatūroje. Gaunama 81 g paruošto krūvininkus transportuojančio junginio.Dissolve 100 g of 4-diethylaminobenzaldehyde 1,1-diphenylhydrazone (m.p.93 ° -94.5 ° C) obtained by condensation of 4-diethylaminobenzaldehyde with N, N-diphenylhydrazine, add 3 g of activated carbon, boil with vigorous stirring and filter. The solution is left to stand at 10 ° -15 ° C. After a day, the precipitated crystals of 4-diethylaminobenzaldehyde 1,1-diphenylhydrazone were filtered off, washed with chilled ethanol (5 ° C) and dried at 40 ° -45 ° C. 81 g of the prepared carrier compound are obtained.
Bandymai ir matavimai buvo atliekami kaip nurodyta 1 pavyzdyje.Tests and measurements were performed as in Example 1.
pavyzdysexample
Ant 40 mm skersmens ir 250 mm ilgio aliumininių cilindrų su barjeriniu 0,8 pm storio poliamido 6/66/610 sluoksniu užnešama fotojautri danga iš monosluoksnio, gauto, panardinant cilindrą j dispersiją, gautą vibrodispergatoriuje 6 h 50° C temperatūroje disperguojant 47,9 svorio dalis polikarbonato (APEC 9202), 47,6 svorio dalis 4-dipropilaminobenzaldehidoAluminum cylinders 40 mm in diameter and 250 mm in length with a barrier layer of 0.8 µm polyamide 6/66/610, coated with a photosensitive monolayer by immersion of the cylinder in a vibrator disperser for 6 h at 50 ° C, with a weight of 47.9 part polycarbonate (APEC 9202), 47.6 parts 4-dipropylaminobenzaldehyde
1-benzil-1-(4-bromfenil) hidrazono, 4,3 svorio dalis fluorenono eilės bisazopigmento, 0,2 svorio dalis stabilizatorių ir 700 svorio dalių tetrahidrofurano.1-benzyl-1- (4-bromophenyl) hydrazone, 4.3 parts by weight of a fluorenone series bisazopigment, 0.2 parts by weight of stabilizers and 700 parts by weight of tetrahydrofuran.
Išdžiovinus, gautas 15 pm storio monosluoksnis.Upon drying, a 15 µm monolayer was obtained.
4-Dipropilaminobenzaldehido 1 benzil-1-(4-bromfenil)hidrazonas gaunamas: 100 g 4-dipropilaminobenzaldehido 1-benzil-1-(4-bromfenil) hidrazono (lydymosi temperatūra - 138°-139,5°C), gauto alkilarilinant 4dipropilaminobenzaldehido ir 4-bromfenilhidrazino kondensacijos produktą benzilchoridu, ištirpinama. Tirpalas, pridėjus 3 g aktyvintos anglies, 5 min.4-Dipropylaminobenzaldehyde 1 Benzyl-1- (4-bromophenyl) hydrazone is obtained from 100 g of 4-dipropylaminobenzaldehyde 1-benzyl-1- (4-bromophenyl) hydrazone (m.p. 138 ° -139.5 ° C) obtained by alkylation of 4dipropylaminobenzaldehyde and the condensation product of 4-bromophenylhydrazine with benzyl chloride, dissolved. A solution of 3 g of activated carbon was added for 5 min.
intensyviai maišant pavirinamas ir nufiltruojamas. Filtratas paliekamas kambario temperatūroje. Po 5 h iškritę 4-dipropilaminobenzaldehido 1-benzil1-(4-bromfenil)hidrazono kristalai nufiltruojami, perplaunami atšaldytu (5° C temperatūros) toluenu, po to etanoliu ir išdžiovinami 50°-60° C temperatūroje. Gaunama 88 g paruošto krūvininkus transportuojančio junginio.Boil and filter with vigorous stirring. Leave the filtrate at room temperature. After 5 h, the precipitated crystals of 4-dipropylaminobenzaldehyde 1-benzyl-1- (4-bromophenyl) hydrazone were filtered off, washed with chilled (5 ° C) toluene followed by ethanol and dried at 50 ° -60 ° C. 88 g of the prepared carrier compound are obtained.
Bandymai ir matavimai buvo atliekami kaip nurodyta 1 pavyzdyje.Tests and measurements were performed as in Example 1.
pavyzdysexample
Viskas buvo daroma kaip nurodyta 1 pavyzdyje, tiktai vietoje 4benzilmetilaminobenzaldehido 1-benzil-1-fenilhidrazono buvo paimtas 4benzilmetilaminobenzaldehido 1 -benzil-1 -(4-metilfenil)hidrazonas.All was done as in Example 1, only 4-benzylmethylaminobenzaldehyde 1-benzyl-1-phenylhydrazone was replaced with 4-benzylmethylaminobenzaldehyde 1 benzyl-1- (4-methylphenyl) hydrazone.
4-Benzilmetilaminobenzaldehido 1 -benzil-1 -(4-metilfenil)hidrazonas gaunamas:4-Benzylmethylaminobenzaldehyde 1-benzyl-1- (4-methylphenyl) hydrazone is obtained from:
100 g 4-benzilmetilamino benzaldehido 1-benzil-1-(4-metilfenil)hidrazonas (lydymosi temperatūra 145,5° - 149° C), gautas alkilarilinant 4benzilmetilaminobenzaldehido ir 4-metilfenilhidrazino reakcijos produktą benzilchloridu, ruošiamas kaip dipropilaminobenzaldehido 1-benzil-1-(4bromfenil) hidrazonas.100 g of 4-benzylmethylamine benzaldehyde 1-benzyl-1- (4-methylphenyl) hydrazone (melting point 145.5 ° -149 ° C) obtained by alkylation of the reaction product of 4-benzylmethylaminobenzaldehyde with 4-methylphenylhydrazine with benzyl chloride is prepared as dipropylaminobenzaldehyde 1-benzyl - (4bromophenyl) hydrazone.
Gaunama 90,5 g paruošto krūvininkus transportuojančio junginio.90.5 g of the prepared charge carrier compound are obtained.
Kartu su organinių elektrofotografinių fotoreceptorių gavimo pavyzdžiais buvo ruošiami ir palyginimo pavyzdžiai. Palyginimo pavyzdžiuose krūvininkus transportuojančios iš hidrazonu grupės medžiagos nebuvo perkristaiinamos iš tolueno.In addition to the preparation of organic electrophotographic photoreceptors, comparative samples were prepared. In the comparative examples, the carrier materials transporting from the hydrazone group were not recrystallized from toluene.
Gautų organinių elektrofotografinių fotoreceptorių bandymų rezultatai pateikti lentelėje.The results of the obtained organic electrophotographic photoreceptor tests are shown in the table.
LentelėTable
Pastaba:Note:
1. Rezultatai nurodyti skliausteliuose priklauso pavyzdžiams, kurie 1 savaitę buvo laikomi Izopare-L.1. The results in parentheses belong to the samples that were stored in Isopare-L for 1 week.
2. Fotojautris S nustatytas bangų ilgiui, kuris atitinka maksimalią fotoreceptoriaus šviesos absorbciją.2. The photosensitivity S is set at a wavelength that corresponds to the maximum light absorption of the photoreceptor.
Lentelėje pateikti pavyzdžiai, kuriuose krūvininkus transportuojančios medžiagos buvo paimtos iš hidrazonų grupės ir preliminariai apdorotos toluene, parodė elektrofotografinių charakteristikų stabilumą. Tuo pačiu metu pavyzdžiai, kuriuose krūvininkus transportuojančios medžiagos nebuvo preliminariai apdorotos toluene, po išlaikymo Izopare-L, parodė neigiamus pokyčius savo charakteristikose.The examples in the table, in which the charge carriers were taken from the hydrazone group and pretreated with toluene, showed the stability of the electrophotographic characteristics. At the same time, samples in which the carrier materials were not pretreated with toluene after storage with Isopare-L showed negative changes in their characteristics.
Claims (6)
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| JPS6488A (en) | 1987-06-22 | 1989-01-05 | Idemitsu Kosan Co Ltd | Production of dichlorosilanes |
| JPS6414058A (en) | 1987-07-09 | 1989-01-18 | Brother Ind Ltd | Printing apparatus |
| JPS6451955A (en) | 1987-08-24 | 1989-02-28 | Matsushita Electric Industrial Co Ltd | Thermal head |
| JPH0198043A (en) | 1987-10-09 | 1989-04-17 | Nec Corp | Dynamic link control system |
| JPH02380A (en) | 1987-11-20 | 1990-01-05 | Canon Inc | Photovoltaic device |
| JPH053349A (en) | 1991-06-25 | 1993-01-08 | Onoda Cement Co Ltd | Laminated piezo-electric actuator and its manufacture |
| JPH052063A (en) | 1991-06-24 | 1993-01-08 | Japan Radio Co Ltd | Gps satellite signal generator |
| EP0618507A1 (en) | 1993-03-29 | 1994-10-05 | Mitsubishi Chemical Corporation | Electrophotographic photoreceptor for liquid development |
| US5492788A (en) | 1994-10-03 | 1996-02-20 | Xerox Corporation | System for replenishing liquid electrostatic developer |
| EP0754977A1 (en) | 1995-07-07 | 1997-01-22 | Lexmark International, Inc. | Electrophotographic photoconductor having improved cycling stability and oil resistance |
| EP0767411A1 (en) | 1995-10-06 | 1997-04-09 | Lexmark International, Inc. | Electrophotographic photoconductor for use with liquid toners |
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1997
- 1997-10-06 LT LT97-159A patent/LT4555B/en not_active IP Right Cessation
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6488A (en) | 1987-06-22 | 1989-01-05 | Idemitsu Kosan Co Ltd | Production of dichlorosilanes |
| JPS6414058A (en) | 1987-07-09 | 1989-01-18 | Brother Ind Ltd | Printing apparatus |
| JPS6451955A (en) | 1987-08-24 | 1989-02-28 | Matsushita Electric Industrial Co Ltd | Thermal head |
| JPH0198043A (en) | 1987-10-09 | 1989-04-17 | Nec Corp | Dynamic link control system |
| JPH02380A (en) | 1987-11-20 | 1990-01-05 | Canon Inc | Photovoltaic device |
| JPH052063A (en) | 1991-06-24 | 1993-01-08 | Japan Radio Co Ltd | Gps satellite signal generator |
| JPH053349A (en) | 1991-06-25 | 1993-01-08 | Onoda Cement Co Ltd | Laminated piezo-electric actuator and its manufacture |
| EP0618507A1 (en) | 1993-03-29 | 1994-10-05 | Mitsubishi Chemical Corporation | Electrophotographic photoreceptor for liquid development |
| US5492788A (en) | 1994-10-03 | 1996-02-20 | Xerox Corporation | System for replenishing liquid electrostatic developer |
| EP0754977A1 (en) | 1995-07-07 | 1997-01-22 | Lexmark International, Inc. | Electrophotographic photoconductor having improved cycling stability and oil resistance |
| EP0767411A1 (en) | 1995-10-06 | 1997-04-09 | Lexmark International, Inc. | Electrophotographic photoconductor for use with liquid toners |
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