JPS62182744A - Electrophotographic sensitive material - Google Patents
Electrophotographic sensitive materialInfo
- Publication number
- JPS62182744A JPS62182744A JP2355086A JP2355086A JPS62182744A JP S62182744 A JPS62182744 A JP S62182744A JP 2355086 A JP2355086 A JP 2355086A JP 2355086 A JP2355086 A JP 2355086A JP S62182744 A JPS62182744 A JP S62182744A
- Authority
- JP
- Japan
- Prior art keywords
- polycarbonate resin
- modified polycarbonate
- resin
- photoreceptor
- base material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title abstract description 10
- 229920005668 polycarbonate resin Polymers 0.000 claims abstract description 23
- 239000004431 polycarbonate resin Substances 0.000 claims abstract description 23
- 229920005989 resin Polymers 0.000 claims abstract description 18
- 239000011347 resin Substances 0.000 claims abstract description 18
- 239000011230 binding agent Substances 0.000 claims abstract description 14
- 108091008695 photoreceptors Proteins 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 abstract description 4
- 238000000576 coating method Methods 0.000 abstract description 4
- 239000007769 metal material Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 1
- 230000000306 recurrent effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- -1 Boliureta 7 Polymers 0.000 description 7
- 239000001294 propane Substances 0.000 description 7
- 229920000515 polycarbonate Polymers 0.000 description 6
- 239000004417 polycarbonate Substances 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 229940097275 indigo Drugs 0.000 description 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- OXNMVZSXDDMZRC-UHFFFAOYSA-N 2-[(2-hydroxyphenyl)-phenylmethyl]phenol Chemical compound OC1=CC=CC=C1C(C=1C(=CC=CC=1)O)C1=CC=CC=C1 OXNMVZSXDDMZRC-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910001370 Se alloy Inorganic materials 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- QLNFINLXAKOTJB-UHFFFAOYSA-N [As].[Se] Chemical compound [As].[Se] QLNFINLXAKOTJB-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- UDYGXWPMSJPFDG-UHFFFAOYSA-M benzyl(tributyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 UDYGXWPMSJPFDG-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 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 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011538 cleaning material Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- WGMBWDBRVAKMOO-UHFFFAOYSA-L disodium;4-[2-(4-oxidophenyl)propan-2-yl]phenolate Chemical compound [Na+].[Na+].C=1C=C([O-])C=CC=1C(C)(C)C1=CC=C([O-])C=C1 WGMBWDBRVAKMOO-UHFFFAOYSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- ZMLDXWLZKKZVSS-UHFFFAOYSA-N palladium tin Chemical compound [Pd].[Sn] ZMLDXWLZKKZVSS-UHFFFAOYSA-N 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0564—Polycarbonates
-
- 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
- G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0582—Polycondensates comprising sulfur atoms in the main chain
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は電子写真感光体に関するものであり、詳しくは
特定のバインダー樹脂を用いた耐久性の優れた亀子写真
感光体に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an electrophotographic photoreceptor, and more particularly to a Kameko photoreceptor with excellent durability using a specific binder resin.
電子写真技術は即時性、高品質の画像が得られることな
どから、近年ではｍｆｆ；４ｍの分野にとどまらず、各
種プリンター分野等でも広く使われ応用されてきている
。In recent years, electrophotographic technology has been widely used and applied not only in the field of MFF; 4m but also in the field of various printers, etc., because of its ability to obtain instant images and high-quality images.
電子写真技術の中核となる感光体については、その光導
電性材料として、従来からのセレニウム、ヒ素−セレニ
ウム合金、係ＩＬ化カドミウム、酸化亜鉛といった無機
系４屯体から、最近では＠蛍である、成膜が容易である
、製造が容易である等の利点を有する有機系の光導電材
料を使用した感光体が開発されている。Regarding photoreceptors, which are the core of electrophotographic technology, photoconductive materials range from conventional inorganic materials such as selenium, arsenic-selenium alloy, cadmium chloride, and zinc oxide, to more recently @hotaru. 2. Description of the Related Art Photoreceptors using organic photoconductive materials have been developed, which have advantages such as easy film formation and easy manufacturing.
有機系の感光体としては、元導こ性徴粉末をバインダー
脂肪中に分散させた、いわゆる分散型感光体、導電性支
持体上に、電荷発生属及び電荷移動層を設けた積層型感
光体等が知られているが、後者のタイプが高感度、高耐
刷性ということで実用に供せられている。Examples of organic photoreceptors include so-called dispersion type photoreceptors in which a conductive powder is dispersed in a binder fat, and laminated type photoreceptors in which a charge generation layer and a charge transfer layer are provided on a conductive support. are known, but the latter type is in practical use because of its high sensitivity and high printing durability.
しかし従来の有機系積層型感光体は感度、帯電性といっ
た電気的性能においては十分な特性を持ち、耐久性を持
つものが開発されているが、物理的な特性において、即
ちトナーによる現像、紙との摩擦、方法によって負荷は
異なるが、クリーニング部材による摩覇などの実用上の
負荷によって摩耗や表面傷を生じてしまうなどの欠点を
有しているだめ、実用上は限られた耐刷性能にとどまっ
ているのが現状である。However, conventional organic laminated photoreceptors have sufficient electrical properties such as sensitivity and chargeability, and some have been developed that are durable. Although the load varies depending on the friction and method used, it has drawbacks such as abrasion and surface scratches due to practical loads such as abrasion caused by cleaning materials, so it has limited printing durability in practical use. The current situation is that it remains at .
こうした表面の物理的強度を決めているのは積層型感光
体においては電荷移動層、特にバインダー樹脂である。In a multilayer photoreceptor, what determines the physical strength of the surface is the charge transfer layer, especially the binder resin.
従来、電荷移動ノ・Ｊのバインダー樹脂としてはポリカ
ーボネー） ８４脂、アクリル樹月旨、メタクリル位（
月旨、ポリエステル樹脂、ポリスチレン樹脂、シリコン
樹脂、エポキシ樹脂、ポリ塩化ビニル樹脂等の熱可塑性
防腸や種々の硬化性樹脂などが用いられてきているが、
通常電荷移動層はバインダー樹脂と成性移動剤の固溶体
からなっておシ、この辺荷移＃］刑のドープ量が相当多
いため、十分な表面強度を持たせるに至っていない。Conventionally, binder resins for charge transfer J include polycarbonate), acrylic resin, methacrylic resin (
Thermoplastic barriers such as polyester resin, polystyrene resin, silicone resin, epoxy resin, and polyvinyl chloride resin, as well as various curable resins, have been used.
Usually, the charge transfer layer is composed of a solid solution of a binder resin and a synthetic transfer agent, and since the amount of doping on this side is quite large, it does not have sufficient surface strength.
そのため通常のブレードクリ−ｊング方式をとったプロ
セスで使用した場合、数千〜／万枚程度のコピーで表面
の摩擦、傷などで画質が損なわれ、感光体は交換せざる
を得なくなる。Therefore, when used in a normal blade cleaning process, the image quality deteriorates due to surface friction and scratches after several thousand to ten thousand copies are made, and the photoreceptor must be replaced.
本発明者らは、感光層のバインダー樹脂について詳細に
倹討した結果、特定の変性ポリカーボネート樹脂を用い
ることにょシ、十分な表面強度を与え、その結果大幅に
耐久性を向上させることができることを見い出した。As a result of careful consideration of the binder resin of the photosensitive layer, the present inventors have found that by using a specific modified polycarbonate resin, sufficient surface strength can be imparted and, as a result, durability can be significantly improved. I found it.
即ち、本発明の要旨は、導電付支持体上に感光層を有す
る電子写真感光体におりて、咳感元層のバインダー樹脂
として、下記一般式＋１１及び（２）で示される祿シ返
し構造単位をＭする変性ポリカーボネート印脂を含有す
ることを特徴とする電子写真感光体にある。That is, the gist of the present invention is to provide an electrophotographic photoreceptor having a photoreceptor layer on a conductive support, and to use, as a binder resin of a cough-sensing layer, a brushed back structure represented by the following general formulas +11 and (2). An electrophotographic photoreceptor is characterized in that it contains a modified polycarbonate sealant having M units.
（但し、式中Ｘは一〇−又は−ＳＯ，−で示されるコ価
の基を示し、芳香ｍＡ及びＢは７以上のアルキル基及び
／又はハロゲン原子を有していてもよい。）
（但し、式中Ｒ１、Ｈ２は水素原子、炭素原子数／〜乙
のアルキル基又はフェニル基、ナフチル基等のアリール
基を示し、芳香ｍｏ及びＤは１以上のアルキル基及び／
又はハロゲン原子を有していてもよい。）
以下本発明の詳細な説明する。(However, in the formula, X represents a covalent group represented by 10- or -SO,-, and the aromatic mA and B may have 7 or more alkyl groups and/or halogen atoms.) However, in the formula, R1 and H2 represent a hydrogen atom, an alkyl group with a carbon atom number of /~2, or an aryl group such as a phenyl group or a naphthyl group, and the aromatics mo and D represent one or more alkyl groups and/or
Or it may have a halogen atom. ) The present invention will be described in detail below.
本発明の感光体は導電性支持体上に設けられる。導電性
の支持体としてはアルミニウム、ステンレス鋼、銅、ニ
ッケルなどの金属材料、表面にアルミニウム、銅、パラ
ジウム酸化スズ、酸化インジウムなど’ｄｐ ”４注心
を設けたポリエステルフィルム、紙などの絶縁性の支持
体が使用される。The photoreceptor of the present invention is provided on a conductive support. Conductive supports include metal materials such as aluminum, stainless steel, copper, and nickel, and insulating materials such as polyester films and paper with aluminum, copper, palladium tin oxide, indium oxide, etc. on the surface. supports are used.
かかる導電性支持体上に分散型、積層型等の感光層が設
けられるが、この間に通常使用されるような公知のバリ
アーノーが設けられていてもよい。バリア一層としては
例えば酸化アルミニウムなどの金属酸化物ポリアミド、
ボリウレタ７、セルロース、カゼインなどの！Ｉｉ脂層
が使用できる。分散型感光体の場合の光導電材料として
は、セレニウム及びその合金、硫化カドミウム、その他
無機系元導電体、フタロシアニン顔料、アゾｆ項科、キ
ナクリドン顔料、インジゴ顔料、ヘリレン顔料、多壊キ
ノン朗料、ベンズイミダゾール糸顔料等の有機顔料が使
用できる。A photosensitive layer of a dispersed type, a laminated type, etc. is provided on such a conductive support, and a commonly used barrier layer may be provided therebetween. As a barrier layer, for example, metal oxide polyamide such as aluminum oxide,
Boliureta 7, cellulose, casein, etc.! Ii fat layer can be used. In the case of a dispersed photoreceptor, photoconductive materials include selenium and its alloys, cadmium sulfide, other inorganic base conductors, phthalocyanine pigments, azo-containing pigments, quinacridone pigments, indigo pigments, helylene pigments, and polydestructive quinone pigments. Organic pigments such as benzimidazole thread pigments can be used.
槓ノｌ型感尤不の場合、その′屯荷発生鳩としては上記
の各檀光導電材料が使用でき、これらの均一層でるるか
、これらの微粒子をポリ酢酸ビニル、ポリアクリル酸エ
ステル、ポリメタクリル酸エステル、ポリエステル、ポ
リカーボネート、ポリビニルブチラール、フェノキシ側
脂、セルロースエステル、セルロースエーテル、ウレタ
ン樹脂、エポキシ佃脂等の各棟バインダー街脂で結后し
た形で使用される。In the case of a non-conductive type of susceptibility, each of the above-mentioned photoconductive materials can be used as the bulk material, and these fine particles can be coated with polyvinyl acetate, polyacrylic ester, polyvinyl acetate, polyacrylic ester, etc. It is used in the form of a binder such as polymethacrylic acid ester, polyester, polycarbonate, polyvinyl butyral, phenoxy side fat, cellulose ester, cellulose ether, urethane resin, epoxy soybean paste, etc.
この層の層厚は通常０．７μｍから７μｍ好ましくは０
．７ ！ｒμｍからＱ、乙ｌＬｍが好適である。The layer thickness of this layer is usually 0.7 μm to 7 μm, preferably 0.
．． 7! Rμm to Q and Lm are suitable.
また、電荷Ｓ動ノーの電荷移動材料としては１、．２．
私？ −）リニトロフルオレノン、テトラシアノキノジ
メタン等の′電子吸引性物質、カルバゾール、インドー
ル、イミダゾール、オキサゾ−／Ｌ＝ 、チアゾール、
オキサジアゾール、ピラゾール、ピラゾリン、チアンア
ゾール等の傾素夕化合！１匁、アニリンの誘導体、ヒド
ラジン誘導体、ヒドラゾンあるいはこれらの化合物から
なる基を主鎖もしくは側鎖に有する本合体等の電子供与
件物質が砂げられる。In addition, as a charge transfer material with charge S movement, 1, . 2.
I? -) Electron-withdrawing substances such as linitrofluorenone and tetracyanoquinodimethane, carbazole, indole, imidazole, oxazo-/L=, thiazole,
Isolated compounds such as oxadiazole, pyrazole, pyrazoline, thianazole, etc.! Electron-donating substances such as 1 monme, aniline derivatives, hydrazine derivatives, hydrazone, or the present compound having a group consisting of these compounds in the main chain or side chain are used.
これらのうちで、特に下記一般式ｆ３１「
（式中、Ｒ１はアルキル基、１を挨アルキル基、または
アラルキル基を表わし、Ｒ４はアルキル基、アリル基、
置換アルキル基、フェニル基、ナフチル基、またはアラ
ルキル基を表わし、２．は水素原子、アルキル基、アル
コキシ基または）・ロゲン原子を表わす。）で表わされ
るヒドラゾン化合物（特開昭ｒａ−ｓｏｉａｔ号公報参
照）若しくは下記一般式（４）
（式中、ＸＩ 、ｙｌおよび２１ は水素原子、低級
アルキル基、低級アルコキシ基、フェノキシ基またはア
リールアルコキシ基を表わし Ｒ５は水素原子、低級ア
ルキル基、アリル基、フェニル基またはアラルキル基を
表わし、ｍおよびｔは／または−を表わし、ｐはＯまた
は／を表わす。）で表わされるヒドラゾン化合物を単独
もしくは混合して使用するのが好ましい。Among these, the following general formula f31 " (wherein R1 represents an alkyl group, 1 represents an alkyl group, or an aralkyl group, and R4 represents an alkyl group, an allyl group,
2. Represents a substituted alkyl group, phenyl group, naphthyl group, or aralkyl group; represents a hydrogen atom, an alkyl group, an alkoxy group, or a rogen atom. ) or the following general formula (4) (wherein XI, yl and 21 are hydrogen atoms, lower alkyl groups, lower alkoxy groups, phenoxy groups or arylalkoxy R5 represents a hydrogen atom, a lower alkyl group, an allyl group, a phenyl group, or an aralkyl group, m and t represent -, and p represents O or /. It is preferable to use them in combination.
災に本発明の電荷移動層には、成膜性、可とり性、機械
的強度を向上させるために、周知の可塑剤、残留電位の
蓄積を抑制するためのム加炸１などの周知の添加剤を含
有していてもよい。Unfortunately, the charge transfer layer of the present invention contains well-known plasticizers and well-known additives 1 to suppress the accumulation of residual potential in order to improve film formability, removability, and mechanical strength. It may contain additives.
本発明の変性ポリカーボネート樹脂は、前記一般式（１
）及び一般式（２）で示される繰り返し構造単位を有す
るものである。通常、分子量は粘度平均分子量で約／
Ｉ２０００−！ｒ０．０００の範囲である。The modified polycarbonate resin of the present invention has the general formula (1
) and a repeating structural unit represented by the general formula (2). Usually, the molecular weight is a viscosity average molecular weight of approximately /
I2000-! r is in the range of 0.000.
かかる変性ポリカーボネート樹脂は、前記感光層のバイ
ンダーとして有利に使用できる。感光層が積層型の場合
、電荷発生層及び電荷移動層の騒ずれのバインダーとし
て使用してもよいが、電荷幾勤層のバインダーとして使
用するのが好ましい。Such a modified polycarbonate resin can be advantageously used as a binder for the photosensitive layer. When the photosensitive layer is of a laminated type, it may be used as a binder for the charge generation layer and the charge transport layer, but it is preferably used as a binder for the charge distribution layer.
本発明の変性ポリカーボネート樹脂は、下記一般式（６
）及び（力から選ばれる一徳以上のフェノール系化合物
を用いて、常法に従い容易に合成することができる。The modified polycarbonate resin of the present invention has the following general formula (6
It can be easily synthesized according to a conventional method using a phenolic compound selected from ) and (ittoku or higher).
（式中Ｘ及び芳香ｆｆ１Ａ及びＢは前記一般式（１）に
て定義したとおりである。）
Ｒ”
（式中Ｒ１１、Ｒ？及び芳香ｌＣ及びＤは前記一般式（
２）で定義したとおりである。）
上記一般式（６）のフェノール系化合物及び一般式（７
）のフェノール系化合物の使用量の比はＳ対ｑｓなりし
５０対コ０１好ましくは、５対９よないしＩＩＱ対６０
の範囲から選ばれる。(In the formula, X and the aromas ff1A and B are as defined in the general formula (1) above.)
As defined in 2). ) The phenolic compound of the above general formula (6) and the general formula (7
) The ratio of the amount of phenolic compound used is S to qs, 50 to 01, preferably 5 to 9 to IIQ to 60.
selected from the range.
ここで一般式（６）で表わされるフェノール系化合物の
具体例は、＋、ｇ’−ジヒドロキシジフェニルスルフィ
ド、 ＆、４＜’−ジヒドロキシー３１Ｊ′−ジメチ
ルジフェニルスルフィドのようなジヒドロキシジアリー
ルスルフィド類、 ＋、ｕ’−ジヒドロキシジフェニ
ルスルホン、ａ、ｙ′−ジヒドロキシ−，３，Ｊ’−ジ
メチルジフェニルスルホンのようなジヒドロキシジアリ
ールスルホン類等が挙げられる。Specific examples of the phenolic compound represented by the general formula (6) include +, g'-dihydroxydiphenyl sulfide, &, dihydroxydiaryl sulfides such as 4<'-dihydroxy-31J'-dimethyldiphenyl sulfide, + , u'-dihydroxydiphenylsulfone, a,y'-dihydroxy-,3,J'-dimethyldiphenylsulfone, and other dihydroxydiarylsulfones.
一般式（７）で表わされるフェノール系化合物の具体例
ｄビス（＋−ヒドロキシフェニル）メタン、／、／−ヒ
ス（ターヒドロキシフェニル）エタン、ｕ、２−ビス（
ＩＩ−ヒドロキシフェニル）プロパン、−２２−ビス（
ターヒドロキシフェニル）ブタン、コ、ニービス（４１
−ヒドロキシ−３−メチルフェニル）プロパン、＋２．
．２−ビス（ｌＩ−ヒドロキシ−３は一ジメチルフェニ
ル）フロパン、−９−一ビス（亭−ヒドロキシ−３１ｓ
−ジブロモフェニル）プロパンのようなビス（ヒドロキ
シアリール）アルカン類、ビス（＋−ヒドロキシフェニ
ル）ジフェニルメタン、ビス（２−ヒドロキシフェニル
）フェニルメタン、／、／−ビス（ｅ−ヒドロキシフェ
ニル）−／−フェニルエタン、／、／−ビス（ターヒド
ロキシフェニル）−７−フェニルプロパン、／、／−ヒ
ス（４ｔ−ヒドロキシフェニル）−／−フェニルブタン
等が挙げられる。Specific examples of phenolic compounds represented by general formula (7) d bis(+-hydroxyphenyl)methane, /, /-his(terhydroxyphenyl)ethane, u, 2-bis(
II-hydroxyphenyl)propane, -22-bis(
terhydroxyphenyl)butane, Co, Nibis (41
-hydroxy-3-methylphenyl)propane, +2.
．． 2-bis(lI-hydroxy-3 is monodimethylphenyl)furopane, -9-bis(tei-hydroxy-31s)
-bis(hydroxyaryl)alkanes such as dibromophenyl)propane, bis(+-hydroxyphenyl)diphenylmethane, bis(2-hydroxyphenyl)phenylmethane, /,/-bis(e-hydroxyphenyl)-/-phenyl Examples include ethane, /,/-bis(terhydroxyphenyl)-7-phenylpropane, /,/-his(4t-hydroxyphenyl)-/-phenylbutane.
本発明の変性ポリカーボネート樹脂を製造する方法は具
体的には堪化メチレン、／、ニージクロロメタン等の不
活性溶媒存在下、前記フェノール系化合物に酸受容体と
してアルカリ水溶液あるいはピリジン等を入れ、ホスゲ
ンを導入しながら反応させる。酸受容体としてアルカリ
水１．：ｇを使う時は、触媒としてトリメチルアミン、
１リエチルアミン等の第３級アミン、あるいはテトラブ
チルアンモニウムクロリド、ベンジルトリブチルアンモ
ニウムプロミド等第４ｔｐアンモニウム化合物を用いる
と反応速度が増大する。Specifically, the method for producing the modified polycarbonate resin of the present invention involves adding an alkaline aqueous solution or pyridine as an acid acceptor to the phenolic compound in the presence of an inert solvent such as dichloromethane, dichloromethane, etc., and then adding phosgene to the phenol compound. React while introducing. Alkaline water as acid acceptor1. : When using g, use trimethylamine as a catalyst,
The reaction rate is increased by using a tertiary amine such as 1-ethylamine or a tertiary tp ammonium compound such as tetrabutylammonium chloride or benzyltributylammonium bromide.
また、必要に応じて分子量調節剤としてフェノール、ｐ
−ターシャリ−ブチルフェノール等−価のフェノールを
共存させてもよい。In addition, as a molecular weight regulator, phenol, p
-Tertiary-butylphenol-equivalent phenol may also be present.
触媒は最初から入れてもよいし、オリゴマーを合成した
後に入れて高分子量化する等任意の方法がとれる。The catalyst may be added from the beginning, or may be added after the oligomer has been synthesized to increase the molecular weight.
尚、本発明において二４１以上のフェノール系化合物を
用いて共重合する方法としては、（イ）二ね以上のフェ
ノール系化合物を最初に同時にホスゲンと反応させて共
重合する方法（０） 一方をまずホスゲンと反応させ
、ある程度反応を行なった後他方を入れて重合する方法
ｅツ 別々にホスゲンと反応させてオリゴマーを合成
し、それらを反応させて重合する方法等の任意の方法が
とれる。In the present invention, methods for copolymerizing using 241 or more phenolic compounds include (a) a method in which two or more phenolic compounds are first simultaneously reacted with phosgene and copolymerized (0) one of them is copolymerized; Any method can be used, such as first reacting with phosgene, reacting to some extent, then adding the other to polymerize, or reacting with phosgene separately to synthesize oligomers, and reacting them to polymerize.
かくして得られる本発明の変性ポリカーボネート樹脂は
、有機浴削に対するｆｔ； Ｍ性が優れており、トルエ
ン、ジオキサン、テトラヒドロフランなどの非ハロゲン
系溶剤に対しても高い溶解性を示し、これらの溶媒を用
いて塗布液の調製ができるため、安全衛生上の問題も少
ない。The modified polycarbonate resin of the present invention obtained in this way has excellent ft; Since the coating solution can be prepared using the same method, there are fewer health and safety issues.
本発明の変性ポリカーボネー ト街脂を用いた感光体は
、繰り返し使用した場合、感度、帯電性の変動が少なく
、従って耐久性が極めて良好である。更に本発明の感光
体は菟子写Ａ腹写機の他、レーザー、ＬＪＩＣＤ、ブラ
ウン管（ＣＲＴ）等を光源とするプリンタの感光体など
成子写真の応用分野にも広く用いることができる。The photoreceptor using the modified polycarbonate street resin of the present invention has little variation in sensitivity and chargeability when used repeatedly, and therefore has extremely good durability. Further, the photoreceptor of the present invention can be widely used in application fields of Seiko photography, such as photoreceptors for printers using lasers, LJICDs, cathode ray tubes (CRTs), etc. as light sources, as well as for A-photographs.
次に本発明を製造例及び実施例により更に具体的に説明
するが、これらは本発明を限定するものではない。なお
、製造例及び実施例中「部」は「重量部」を示す。Next, the present invention will be explained in more detail with reference to production examples and examples, but these are not intended to limit the present invention. In addition, "parts" in the production examples and examples indicate "parts by weight."
製造例−／ （実施例−／の変性ポリカーボネート樹脂
）ｕ、４ｔ’−ジヒドロキシジフェニルスルフィド
ｌｏｏ部コ、−一ビス（ｑ−ヒドロキシフェニル）プロ
パン ３５部ｐ−ターシャリープグ°ルフェノール
Ｊｌ、２部ピリジン
５００部塩化メチレン −３００部上記
混合物を攪拌機つき反応器に仕込み、ｓ ｏ ｏ ｒｐ
ｍで攪拌した。次にホスタフ５０部を７時間かけて吹き
込み、溶液重合を行なった。Production Example-/ (Modified polycarbonate resin of Example-/) u,4t'-dihydroxydiphenyl sulfide
Loo part, -bis(q-hydroxyphenyl)propane 35 parts p-tert-gluphenol
Jl, 2 parts pyridine
500 parts Methylene chloride - 300 parts The above mixture was charged into a reactor equipped with a stirrer, and
The mixture was stirred at m. Next, 50 parts of Hostaf was blown into the solution over 7 hours to carry out solution polymerization.
反応終了後、塩酸水溶液で過剰のピリジンを中和し、除
去した後、水酸化ナトリウム水浴液、塩酸水浴液、つい
で水を用いて洗痒し、最後に塩化メチレンを蒸発させて
樹脂を取シ出した。After the reaction is complete, excess pyridine is neutralized and removed with an aqueous hydrochloric acid solution, washed with a sodium hydroxide bath, a hydrochloric acid bath, and then water, and finally the methylene chloride is evaporated to remove the resin. I put it out.
ＮＭＲの分析結果よりλ、−一ビス（ターヒドロキシフ
ェニル）プロパンのｆａｃｅ ３！ｒ 重ｆ！Ａ テ；
Ｊ）つた。またこの樹脂の平均分子量は１ｙｂｏｏであ
った。From the NMR analysis results, λ, -1-bis(terhydroxyphenyl)propane face 3! r heavy f! A Te;
J) Ivy. Moreover, the average molecular weight of this resin was 1yboo.
ここで１５平均分子量とは、ポリマーｔ、、ｏｉ／１ｏ
ｒＢ化メチレン溶液を用い、−０℃で測定されるηＥ３
ｐから下記の式−（１１および式−（２）よシ氷められ
る値である。Here, 15 average molecular weight means polymer t,, oi/1o
ηE3 measured at -0°C using rB methylene solution
This is the value calculated from p according to the following equations (11 and 2).
ηｏｐ１０＝（η、１（／＋に’ηｓｐ） ・・・
・・・（１）〔η） ＝ ＫＭ”
・・・・・・（２）式中 Ｃポリマーの度 、、！７
７”Ｌ〔η〕極限粘度
に′ ＝ Ｏ６＋２ｇ
ｋｂ ” ／ ａλ３Ｘ１０−′
【工 ＝０．ｇＪ
Ｍ 平均分子量
製造側御 （実り一例−ダの変性ポリカーボネート樹脂
）ｘ、ｔｔ′−ジヒドロキシジフェニルスルホ／ｉｏｔ
ｍユ、２−ビス（９−ヒドロキンフェニル）プロパン
／ ００部ｐ−ターシャリ−ブチルフェノール
２．７部ピリジン ５００
部塩化メチレン コ３００部上記混合
物を製造例／と同様にして溶液重合を行なった。生成し
たポリカーボネート樹脂のＮＭＲ分析の結果％’ ＜＜
、ｇ’−ジヒドロキシジフェニルスルホンの藍は７五量
免であった。ηop10=(η, 1(/+ to 'ηsp)...
...(1) [η) = KM”
......(2) In the formula, the degree of C polymer ,,! 7
7"L [η] Intrinsic viscosity ' = O6 + 2g kb " / aλ3X10-' [Eng = 0. gJ M Average molecular weight Production side control (Example of fruitfulness - modified polycarbonate resin) x, tt'-dihydroxydiphenylsulfo/iot
myu, 2-bis(9-hydroquinphenyl)propane
/ 00 parts p-tert-butylphenol
2.7 parts pyridine 500
30 parts of methylene chloride The above mixture was subjected to solution polymerization in the same manner as in Production Example. Results of NMR analysis of the produced polycarbonate resin %'<<
, g'-dihydroxydiphenylsulfone indigo was 75 doses.
またこの樹脂の平均分子量はユニ〇〇〇であった。Moreover, the average molecular weight of this resin was uni〇〇〇.
製造例−３（実施例−一の変性ポリカーボネート樹脂）
ビ〕 オリゴマーの製造
水酸化ナトリウム水溶液に２．ニービス（ｑ−ヒドロキ
シフェニル）プロパン（ビスフェノールＡ）を溶解して
調整したビスフェノールＡナトリウム塩の／ルミ ６Ｗ
′ｃｚ＆水溶液１００部
ｐ−ターシャリ−ブチルフェノール 。、
２３部塩化メチレン 、。部ホ
スゲン ７部上記組成の
混合物を定量的にパイプリアクターへ供給し界面重合を
行なった。反応混合物を分散し、ポリカーボネートオリ
ゴマーを含有する塩化メチレン溶液のみを捕集した。Production Example-3 (Example-1 modified polycarbonate resin)
[Bi] Production of oligomer 2. Add sodium hydroxide aqueous solution. /Lumi 6W of bisphenol A sodium salt prepared by dissolving Nibis(q-hydroxyphenyl)propane (bisphenol A)
'cz & aqueous solution 100 parts p-tert-butylphenol. ,
23 parts methylene chloride. 7 parts phosgene A mixture having the above composition was quantitatively supplied to a pipe reactor to perform interfacial polymerization. The reaction mixture was dispersed and only the methylene chloride solution containing the polycarbonate oligomer was collected.
得られたオリゴマーの塩化メチレン溶液の分析結果は下
記のとおυであった。The analysis results of the methylene chloride solution of the obtained oligomer were as follows.
オリゴマー濃度 コグＪ重ｉ方末總
りロロホーメート基儂度 ／、３規定末端フ工ノ
ール件水酸基濃度 ０．３３規定斡）変性ポリカー
ボネート樹脂の製造
げ）で製造したオリゴマー溶液 ｌＡＯ部塩
化メチレン ７３０部上記混合物を、攪
拌機料反応器に仕込み、！ｒ ｊ Ｏｒｐｍで攪拌した
。更に下記組成の水溶溶、すなわち、
水酸化ナトリウムのコ！当水溶液 に
部トリエチルアミンの一３水ｆｌｊＨ／部を加え、一時
間界面重合を行ない、反応混合物を分液しポリカーボネ
ート樹脂を含む塩化メチレン溶液を、水、塩酸水溶液、
ついで水を用いて洗浄し、最後に塩化メチレンを蒸発さ
せて樹脂を取シ出した。Oligomer concentration Cog J weight i side entangled roloformate basicity /, 3N terminal phenolic hydroxyl group concentration 0.33N □) Production of modified polycarbonate resin) Oligomer solution produced in 1AO part Methylene chloride 730 parts above Charge the mixture into a stirrer reactor and! Stirred at rj Orpm. Furthermore, an aqueous solution with the following composition, that is, sodium hydroxide! To this aqueous solution, 1 part triethylamine (flj H/part) was added, interfacial polymerization was carried out for 1 hour, and the reaction mixture was separated into two parts.
The resin was then washed with water and finally the methylene chloride was evaporated to remove the resin.
この樹脂の平均分子量はユ＆ｓｏｏであった。The average molecular weight of this resin was y/soo.
実施例／
下記構造を有するビスアゾ化合物７０部とフェノキシ樹
脂（ユニオンカーバイト社製ＰＫＨＨ）５部、ポリビニ
ルブチラール樹脂（積水化学工儒社製ＥＨ−，７）ｓ部
にグーメトキシ−ｑ−メチ・ペンタノン４７２ ７００
部を加え、サンドグラｆンドミルにて粉砕分散処理を行
なった。得られた分散液を厚さ／ ００ ａｍのポリエ
ステルフィルムに蒸着したアルミニウム蒸着層の上にフ
ィルムアプリケーターで乾燥Ｈ厚がｏ、ｔ、ｔ９／Ｉｄ
となる様に塗布した後乾燥した。Example/ 70 parts of a bisazo compound having the following structure, 5 parts of phenoxy resin (PKHH manufactured by Union Carbide Co., Ltd.), s part of polyvinyl butyral resin (EH-, 7 manufactured by Sekisui Chemical Co., Ltd.) and goomethoxy-q-methypentanone. 472 700
of the mixture was added, and pulverization and dispersion treatment was performed using a sand grind mill. The obtained dispersion was applied to an aluminum vapor-deposited layer deposited on a polyester film with a thickness of /00 am using a film applicator to give a dry H thickness of o, t, t9/Id.
It was applied and dried.
この様にして得られた電荷発生層上に、Ｎ −メチルカ
ルバソール−３−アルデヒドジフェニル上２２１フ８０
部及び下記構造を有する変性ポリカーボネート樹脂１０
０部
及び下記構造のシアノ化合物ダ、！部を／、ダージオキ
サンタ００部に溶解した溶液を乾燥膜厚／３μｍとなる
↓うに塗布して電荷移動層を形成させ、積層形の感光体
／−Ａを作成した。On the charge generating layer obtained in this way, 221 80 ml of N-methylcarbasol-3-aldehyde diphenyl
Modified polycarbonate resin 10 having the following structure and
0 parts and a cyano compound with the following structure,! A charge transfer layer was formed by coating a solution prepared by dissolving 1 part in 00 parts of dioxantane to a dry film thickness of 3 .mu.m, to prepare a laminated photoreceptor /-A.
この様にして（ｊられた感光体の特注を次の様にして測
定した。The custom-made photoreceptor manufactured in this way was measured in the following manner.
まず、暗所で感光体へ流れ込むコロナ電流が一＝μＡと
なる様にコロナ数社を行ない、一定速就（／ ｊ Ｏｍ
ａ／ ｓθＣ）で感光体を通過して帝直させ、その帯；
圧を測定し、初勘帯′１圧ＶＯを求めた。次に！ｒ Ｌ
ｕｘの照度の白色光で蕗元し感光体の表面電位が初期帯
電圧よシ半減するために要する露光量Ｅ％として求めた
。First, conduct several corona tests in a dark place so that the corona current flowing into the photoreceptor is 1 = μA, and then obtain a constant speed (/ j Om
Pass through the photoreceptor at a/sθC) and make the band;
The pressure was measured and the initial pressure range '1 pressure VO was determined. next! r L
The exposure amount E% required to reduce the surface potential of the photoreceptor by half of the initial charged voltage by exposing the photoreceptor to white light with an illuminance of ux was determined.
その結果を表−一に示す。The results are shown in Table 1.
実施例コール
実施例／で用いた変性ポリカーボネート樹脂のかわシに
下記表−／に示す変性ポリカーボネート樹脂を用いた他
は実施列ｌと同様にしてそれぞれ感光体ニーＢ、 、？
−０、ダーＤ、 ｊ−ｎｕ、 Ａ −Ｆ。EXAMPLE The procedure was the same as in Example 1 except that the modified polycarbonate resin shown in the table below was used as the base of the modified polycarbonate resin used in Example 1. Photoreceptor knees B, , and ?
-0, Dar D, j-nu, A-F.
を作成し、実施例／と同様その特性を測定した。was prepared and its characteristics were measured in the same manner as in Example.
その結果を表−コに示す。The results are shown in Table C.
表 −／
比較例−／
実施例／で用いた変性ポリカーボネート樹脂のかわシに
市販のポリカーボネート腐脂（コービロン日−１ｏｏｏ
三菱ガス化学＠製）を用いて、実施例／と同様にして感
光体／−Ｅを作成した。Table - / Comparative example - / Commercially available polycarbonate fat (Corbilon day-1ooo
Photoreceptor /-E was prepared in the same manner as in Example / using Mitsubishi Gas Chemical @).
この感光体の特性を実施例／と同様に測定した。The characteristics of this photoreceptor were measured in the same manner as in Example.
その結果を衣−／に示す。The results are shown below.
表 −一
実施例 感光体 帯電圧（至） 残留電位間
半減露光量／ ／−Ａ ！ｔ’ｙｖ
ｔｉｖ ／、２Ｊ’Ｊｍｅｅｃコ
ニーＢ ！り（７ＩＩ
／、、３！；３３−０ ６コ（７Ａ
／護ＯＱ ＩＩ−Ｄ ル１３
ダ ／、３３ＳＳ−兄 １０！；
！； ／、ＱＯＡ ４−Ｆ’
４０ ｊ ／、、Ｉｇ比較
例−／ ／−Ｂ ！１０ Ａ’
／、ｌＩｒ表−一かられかるように本発明の感
光体は、市販のポリカーボネート樹脂を用いた感光体と
比較し、いずれも電気的性能に関し優れてｂることがわ
かる。Table - One Example Photoreceptor Charged Voltage (To) Residual Potential
Half-reduced exposure amount / /-A! t'yv
tiv/, 2J'Jmeec Connie B! ri (7II
/,,3! ;33-0 6 pieces (7A
/ Mamoru OQ II-D Le 13
Da /, 33SS-Brother 10! ;
! ; /, QOA 4-F'
40 j /,, Ig comparative example-/ /-B! 10 A'
As can be seen from Table 1, the photoreceptor of the present invention is superior in electrical performance to photoreceptors using commercially available polycarbonate resins.
実施例−７
実施例／で用いた顔料分散数に、表面鏡面仕上げＬ７’
ｊアルミニウムシリンダーを浸漬塗布し、乾燥後の映ノ
！ｌがθ、ダμｍとなる様厄荷発生層を設けた。次にこ
のアルミシリンダーを実施例／で用いた屯荷移ｍ削、ポ
リカーボネート樹脂！脂の／、４（−ジオキサン溶液に
浸漬塗布し転線後の膜厚が７５４ｍとなる様電荷移動層
を設けた。Example-7 The pigment dispersion number used in Example/ has a surface mirror finish L7'
j After coating the aluminum cylinder by dip coating and drying it! The burden generation layer was provided so that l was θ and da μm. Next, this aluminum cylinder was used in the Example/Total transfer m cutting, polycarbonate resin! A charge transfer layer was provided by dip coating in a dioxane solution of fat/4(-) so that the film thickness after wire transfer was 754 m.
この様にして作成したドラム状感光体を７４とする。ま
た同様に比較例−／のドラム状感光体／−Ｃも作成した
。The drum-shaped photoreceptor produced in this manner is designated as 74. In addition, a drum-shaped photoreceptor/-C of Comparative Example-/ was also prepared in the same manner.
これらの感光体の耐久性を評価するため、ブレードクリ
ーニング方式の市販の複写機にこれらの感光体をとりつ
けコピーテストを行なった。In order to evaluate the durability of these photoreceptors, these photoreceptors were attached to a commercially available copying machine with a blade cleaning method and a copy test was conducted.
ピの結果比較例サンプル／−〇では一万枚のコピーで感
光体表面に傷が生じ始め、コピー画像上でも若干黒い筋
となって現われたのに対し、感光体クーＧではダ万枚の
コピーにおいても、感光体表面の傷は少なく、コピー画
像上にも黒い筋はほとんど現われず、良好なコピー画像
が得られた。Comparative Example Sample / -0 started to have scratches on the photoreceptor surface after 10,000 copies, and some black streaks appeared on the copied images, whereas with the photoreceptor Ku G, after 10,000 copies. In copying, there were few scratches on the surface of the photoreceptor, and almost no black streaks appeared on the copied image, and a good copied image was obtained.
また電位特性も表−３のとおりで極めて安定しており十
分な耐久性を有していると判断できる。Further, the potential characteristics are extremely stable as shown in Table 3, and can be judged to have sufficient durability.
表 −３
以上の結果から明らかなように、本発明の変性ポリカー
ボネート樹脂を用いた感光体は、優れた耐久性を有して
いると考えられる。Table 3 As is clear from the above results, the photoreceptor using the modified polycarbonate resin of the present invention is considered to have excellent durability.
Claims (2)
において、該感光層のバインダー樹脂として、下記一般
式（１）及び（２）で示される繰り返し構造単位を有す
る変性ポリカーボネート樹脂を含有することを特徴とす
る電子写真感光体。 ▲数式、化学式、表等があります▼・・・（１） （但し、式中Ｘは−Ｓ−又は−ＳＯ＿２−で示される２
価の基を示し、芳香環Ａ及びＢは１以上のアルキル基及
び／又はハロゲン原子を有していてもよい。） ▲数式、化学式、表等があります▼・・・（２） （但し、式中Ｒ＾１、Ｒ＾２は水素原子、炭素原子数１
〜６のアルキル基又はアリール基を示し、芳香環Ｃ及び
Ｄは１以上のアルキル基及び／又はハロゲン原子を有し
ていても良い。）(1) An electrophotographic photoreceptor having a photosensitive layer on a conductive support, containing a modified polycarbonate resin having repeating structural units represented by the following general formulas (1) and (2) as a binder resin for the photosensitive layer. An electrophotographic photoreceptor characterized by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(1) (However, in the formula, X is -S- or -SO_2-2)
It represents a valent group, and the aromatic rings A and B may have one or more alkyl groups and/or halogen atoms. ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(2) (However, in the formula, R^1 and R^2 are hydrogen atoms and the number of carbon atoms is 1.
~6 alkyl groups or aryl groups, and the aromatic rings C and D may have one or more alkyl groups and/or halogen atoms. )
及び（２）で示される繰り返し構造単位の含有比が５対
９５ないし８０対２０の樹脂であることを特徴とする特
許請求範囲第１項記載の電子写真感光体。(2) The modified polycarbonate resin has the general formula (1)
The electrophotographic photoreceptor according to claim 1, wherein the content ratio of the repeating structural units represented by (2) is 5:95 to 80:20.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61023550A JPH06105357B2 (en) | 1986-02-05 | 1986-02-05 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61023550A JPH06105357B2 (en) | 1986-02-05 | 1986-02-05 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62182744A true JPS62182744A (en) | 1987-08-11 |
| JPH06105357B2 JPH06105357B2 (en) | 1994-12-21 |
Family
ID=12113593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61023550A Expired - Fee Related JPH06105357B2 (en) | 1986-02-05 | 1986-02-05 | Electrophotographic photoreceptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06105357B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0393787A2 (en) * | 1989-04-21 | 1990-10-24 | Agfa-Gevaert N.V. | Electrophotographic recording material |
| EP0402979A1 (en) * | 1989-06-16 | 1990-12-19 | Agfa-Gevaert N.V. | Electrophotographic recording material |
| JP2004264642A (en) * | 2003-03-03 | 2004-09-24 | Mitsubishi Chemicals Corp | Electrophotographic photoreceptor |
| WO2017208700A1 (en) * | 2016-05-31 | 2017-12-07 | 京セラドキュメントソリューションズ株式会社 | Electrophotographic photoreceptor, process cartridge, and image forming device |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57200046A (en) * | 1981-06-03 | 1982-12-08 | Toray Ind Inc | Transparent electrophotographic receptor |
-
1986
- 1986-02-05 JP JP61023550A patent/JPH06105357B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57200046A (en) * | 1981-06-03 | 1982-12-08 | Toray Ind Inc | Transparent electrophotographic receptor |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0393787A2 (en) * | 1989-04-21 | 1990-10-24 | Agfa-Gevaert N.V. | Electrophotographic recording material |
| EP0402979A1 (en) * | 1989-06-16 | 1990-12-19 | Agfa-Gevaert N.V. | Electrophotographic recording material |
| JP2004264642A (en) * | 2003-03-03 | 2004-09-24 | Mitsubishi Chemicals Corp | Electrophotographic photoreceptor |
| WO2017208700A1 (en) * | 2016-05-31 | 2017-12-07 | 京セラドキュメントソリューションズ株式会社 | Electrophotographic photoreceptor, process cartridge, and image forming device |
| JPWO2017208700A1 (en) * | 2016-05-31 | 2019-03-14 | 京セラドキュメントソリューションズ株式会社 | Electrophotographic photosensitive member, process cartridge, and image forming apparatus |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06105357B2 (en) | 1994-12-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4956256A (en) | Photosensitive member for electrophotography | |
| US5283142A (en) | Image-holding member, and electrophotographic apparatus, apparatus unit, and facsimile machine employing the same | |
| JPH10288845A (en) | Resin for forming electrophotographic photoreceptor | |
| JPH0820739B2 (en) | Electrophotographic photoreceptor | |
| JP2568352B2 (en) | Electrophotographic photoreceptor, electrophotographic apparatus and apparatus unit having the same | |
| JPS62182744A (en) | Electrophotographic sensitive material | |
| JP3250295B2 (en) | Electrophotographic photoreceptor | |
| JPS6365444A (en) | Electrophotographic sensitive body | |
| JP2531890B2 (en) | Image holding member, electrophotographic apparatus using the same, apparatus unit and facsimile | |
| JP2001206943A (en) | Electrophotographic photoreceptor | |
| JP2002072511A (en) | Monolayer-type electrophotographic photoreceptor | |
| US5418098A (en) | Electrophotographic photosensitive member, and electrophotographic apparatus, device unit and facsimile machine having the photosensitive member | |
| JPH0727223B2 (en) | Electrophotographic photoreceptor | |
| JP4372937B2 (en) | Electrophotographic photoreceptor | |
| JP2001209195A (en) | Electrophotographic photoreceptor | |
| JPS60205454A (en) | Electrophotographic sensitive body | |
| JP2572818B2 (en) | Electrophotographic photoreceptor | |
| JP2870920B2 (en) | Electrophotographic photoreceptor | |
| JP3560116B2 (en) | Polycarbonate, method for producing the same, and electrophotographic photosensitive member | |
| JPH0728255A (en) | Electrophotographic photoreceptor | |
| JP3844797B2 (en) | Image forming method | |
| JPH01312548A (en) | Electrophotographic sensitive body | |
| JP3397010B2 (en) | Polycarbonate, method for producing the same, and electrophotographic photoreceptor using polycarbonate | |
| JPH0915874A (en) | Electrophotographic photoreceptor | |
| JP3944028B2 (en) | Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |