JPS62208055A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPS62208055A JPS62208055A JP5067886A JP5067886A JPS62208055A JP S62208055 A JPS62208055 A JP S62208055A JP 5067886 A JP5067886 A JP 5067886A JP 5067886 A JP5067886 A JP 5067886A JP S62208055 A JPS62208055 A JP S62208055A
- Authority
- JP
- Japan
- Prior art keywords
- layer
- silicone
- formula
- photosensitive
- substrate
- 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.)
- Pending
Links
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 48
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 36
- 229920005989 resin Polymers 0.000 claims abstract description 32
- 239000011347 resin Substances 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 238000006482 condensation reaction Methods 0.000 claims abstract description 5
- 229920001577 copolymer Polymers 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 73
- 108091008695 photoreceptors Proteins 0.000 claims description 29
- 239000002344 surface layer Substances 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 abstract description 24
- 229920000642 polymer Polymers 0.000 abstract description 9
- 238000004140 cleaning Methods 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 description 21
- 238000000034 method Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000000576 coating method Methods 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 13
- 239000000049 pigment Substances 0.000 description 13
- 229920002545 silicone oil Polymers 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 239000000123 paper Substances 0.000 description 8
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 238000005299 abrasion Methods 0.000 description 5
- 239000011324 bead Substances 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000004576 sand Substances 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000003618 dip coating Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920006311 Urethane elastomer Polymers 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 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
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000012690 ionic polymerization Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000000843 powder Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZKJNETINGMOHJG-GGWOSOGESA-N (e)-1-[(e)-prop-1-enoxy]prop-1-ene Chemical compound C\C=C\O\C=C\C ZKJNETINGMOHJG-GGWOSOGESA-N 0.000 description 1
- KYPOHTVBFVELTG-OWOJBTEDSA-N (e)-but-2-enedinitrile Chemical compound N#C\C=C\C#N KYPOHTVBFVELTG-OWOJBTEDSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- VOCDJQSAMZARGX-UHFFFAOYSA-N 1-ethenylpyrrolidine-2,5-dione Chemical compound C=CN1C(=O)CCC1=O VOCDJQSAMZARGX-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- IWUACMRENZNWBB-UHFFFAOYSA-N 2-(2-chlorophenyl)-1,3-oxazole Chemical compound ClC1=CC=CC=C1C1=NC=CO1 IWUACMRENZNWBB-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical compound ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- MZNSQRLUUXWLSB-UHFFFAOYSA-N 2-ethenyl-1h-pyrrole Chemical compound C=CC1=CC=CN1 MZNSQRLUUXWLSB-UHFFFAOYSA-N 0.000 description 1
- LWFUFLREGJMOIZ-UHFFFAOYSA-N 3,5-dinitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LWFUFLREGJMOIZ-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
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IFNOHRAIEWTBBC-UHFFFAOYSA-N 4-[2-[3-[4-(diethylamino)phenyl]-2-phenyl-1,3-dihydropyrazol-5-yl]-3-phenylprop-1-enyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=C(C=1NN(C(C=1)C=1C=CC(=CC=1)N(CC)CC)C=1C=CC=CC=1)CC1=CC=CC=C1 IFNOHRAIEWTBBC-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- LSZJZNNASZFXKN-UHFFFAOYSA-N 9-propan-2-ylcarbazole Chemical compound C1=CC=C2N(C(C)C)C3=CC=CC=C3C2=C1 LSZJZNNASZFXKN-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- QCGAGFRXAJKVBJ-UHFFFAOYSA-N CCN(CC)C(C=C1)=CC=C1C1=NC(C(C=C2)=CC=C2N(C)C)=CO1 Chemical class CCN(CC)C(C=C1)=CC=C1C1=NC(C(C=C2)=CC=C2N(C)C)=CO1 QCGAGFRXAJKVBJ-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- ZTWQZJLUUZHJGS-UHFFFAOYSA-N Vat Yellow 4 Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C4=CC=CC=C4C(=O)C4=C3C2=C1C=C4 ZTWQZJLUUZHJGS-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- HSUIVCLOAAJSRE-UHFFFAOYSA-N bis(2-methoxyethyl) benzene-1,2-dicarboxylate Chemical compound COCCOC(=O)C1=CC=CC=C1C(=O)OCCOC HSUIVCLOAAJSRE-UHFFFAOYSA-N 0.000 description 1
- 238000000861 blow drying Methods 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- ARLJCLKHRZGWGL-UHFFFAOYSA-N ethenylsilicon Chemical class [Si]C=C ARLJCLKHRZGWGL-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 230000003090 exacerbative effect Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 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
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- 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 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- VPKVQYMSVYDZPL-UHFFFAOYSA-N n,n-diethyl-4-[2-(2-phenyl-1,3-dihydropyrazol-5-yl)ethenyl]aniline Chemical class C1=CC(N(CC)CC)=CC=C1C=CC1=CCN(C=2C=CC=CC=2)N1 VPKVQYMSVYDZPL-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- XRWSIBVXSYPWLH-UHFFFAOYSA-N n-phenyl-n-[(4-pyrrolidin-1-ylphenyl)methylideneamino]aniline Chemical compound C1CCCN1C(C=C1)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 XRWSIBVXSYPWLH-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical compound C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000008096 xylene Substances 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
- G03G5/0592—Macromolecular compounds characterised by their structure or by their chemical properties, e.g. block polymers, reticulated polymers, molecular weight, acidity
-
- 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
-
- 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
- G03G5/0571—Polyamides; Polyimides
-
- 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
- G03G5/0578—Polycondensates comprising silicon atoms in the main chain
-
- 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
- G03G5/147—Cover layers
- G03G5/14708—Cover layers comprising organic material
- G03G5/14713—Macromolecular material
- G03G5/14747—Macromolecular material obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- G03G5/14773—Polycondensates comprising silicon atoms in the main chain
-
- 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
- G03G5/147—Cover layers
- G03G5/14708—Cover layers comprising organic material
- G03G5/14713—Macromolecular material
- G03G5/14791—Macromolecular compounds characterised by their structure, e.g. block polymers, reticulated polymers, or by their chemical properties, e.g. by molecular weight or acidity
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、電子写真複写機、レーザービームプリンター
、CRTプリンター、電子写真式製版システムなどの電
子写真応用分野に広く用いることができる電子写真感光
体に関する。Detailed Description of the Invention [Field of Industrial Application] The present invention is an electrophotographic photosensitive material that can be widely used in electrophotographic application fields such as electrophotographic copying machines, laser beam printers, CRT printers, and electrophotographic plate making systems. Regarding the body.
電子写真感光体の光導電材料としてセレン、硫化カドミ
ウム、酸化亜鉛などの無機光導電材料が従来より用いら
れている。一方ポリビニル力ルバゾール、オキサジアゾ
ール、フタロシアニンなどの有機光導電材料は無機光導
電材料に較べて無公害性、高生産性などの利点があるが
、感度が低くその実用化は困難であった。そのため、い
くつかの増悪方法が提案されているが、効果的な方法と
しては電荷発生層と電荷輸送層を積層した機能分離型感
光体を用いることが知られ実用化されている。Inorganic photoconductive materials such as selenium, cadmium sulfide, and zinc oxide have conventionally been used as photoconductive materials for electrophotographic photoreceptors. On the other hand, organic photoconductive materials such as polyvinyl rubber, oxadiazole, and phthalocyanine have advantages over inorganic photoconductive materials, such as non-pollution and high productivity, but their low sensitivity has made it difficult to put them into practical use. For this reason, several methods have been proposed for exacerbating the problem, but it is known and put into practical use as an effective method to use a functionally separated photoreceptor in which a charge generation layer and a charge transport layer are laminated.
一方、電子写真感光体には、当然のことであるが、適用
される電子写真プロセスに応じた所定の感度、電気特性
、更には光学特性を備えていることが要求される。特に
繰返し使用可能な感光体にあってはその感光体の表面層
、即ち基体より最も離隔する層にはコロナ帯電、トナー
現像、紙への転写、クリーニング処理などの電気的機械
的外力が直接に加えられるため、それらに対する耐久性
が要求される。具体的には、コロナ帯電時に発生するオ
ゾンによる劣化のために感度低下や電位低下、残留電位
増加、お゛よび摺擦による表面の摩耗や傷の発生などに
対する耐久性が要求されている。On the other hand, as a matter of course, electrophotographic photoreceptors are required to have predetermined sensitivity, electrical properties, and optical properties depending on the electrophotographic process to which they are applied. In particular, for photoreceptors that can be used repeatedly, the surface layer of the photoreceptor, that is, the layer furthest from the substrate, is directly exposed to electrical and mechanical external forces such as corona charging, toner development, transfer to paper, and cleaning processing. Since these materials are added, durability against them is required. Specifically, it is required to have durability against a decrease in sensitivity, a decrease in potential, an increase in residual potential due to deterioration due to ozone generated during corona charging, and the occurrence of surface abrasion and scratches due to rubbing.
又、紙との接触による紙粉の付着は、高湿下での画像流
れの原因の一つとなり、又、トナーのフィルミングやク
リーニング不良による残留トナーは、得られる画像を著
しく損ねるものであり、従って、これらに汚染されにく
くかつ容易に除去されやすい感光体表面を形成させるこ
とが要求されている。In addition, adhesion of paper dust due to contact with paper is one of the causes of image fading under high humidity conditions, and toner filming and residual toner due to poor cleaning can significantly impair the resulting image. Therefore, there is a need to form a photoreceptor surface that is less susceptible to contamination and easier to remove.
従来より前記欠点を解決すべ(種々の方法が提案されて
いる。その一つとして、マレインイミド系樹脂を表面層
のバインダーとして用いることが検討されている。マレ
インイミド系樹脂は、電子写真感光体用バインダーとし
て用いた場合、電荷輸送剤等と類似した極性構造を持つ
為、相溶性に優れ、良好な電子写真特性が得られる。し
かしながら耐摩耗性に劣り、実際の複写機に装着した場
合、クリーナー、紙等との接触摩耗及びトナー融着が早
期に発生する。これを改良すべく表面層に潤滑性を付与
させ、すべり抵抗を低減させ結果的に、摩耗量を低減さ
せ、かつトナーの融着を防ぐ事が試みられている。その
手段として、一般的な塗膜表面改質剤、すなわちレベリ
ング剤、シリコーンオイル等の添加やテフロン粉末等を
分散させる方法がある。Conventionally, various methods have been proposed to solve the above-mentioned drawbacks. As one of them, the use of maleimide resin as a binder for the surface layer is being considered. When used as a binder, it has a polar structure similar to charge transport agents, etc., so it has excellent compatibility and good electrophotographic properties. However, it has poor abrasion resistance, and when installed in an actual copying machine, Contact wear with cleaners, paper, etc. and toner fusion occur early.To improve this, the surface layer is given lubricity to reduce sliding resistance, resulting in less wear and toner retention. Attempts have been made to prevent fusion.Means include adding general coating film surface modifiers, ie, leveling agents, silicone oil, etc., and dispersing Teflon powder.
しかしながら、これら一般的な表面改質剤は、添加され
る塗工液の成分との相溶性に乏しいため、長期使用の間
に表面層の上に移行ないし滲み出してくるので効果の持
続性に難点があった。また、表面層自体が光導電層を形
成している場合、表面改質剤が光導電性物質との相溶性
に乏しく、さらに光生成によるキャリヤーの移動に対し
てトラップとなり易く、繰返し電子写真プロセスにより
残留電荷が増大していく傾向があった。一方テフロン粉
末などを分散させた表面層においては分散性不良、透明
性低下、キャリヤーのトラップなどの問題を生じていた
。However, these general surface modifiers have poor compatibility with the components of the coating liquid to which they are added, so they migrate or ooze out onto the surface layer during long-term use, reducing the sustainability of their effects. There was a problem. In addition, when the surface layer itself forms a photoconductive layer, the surface modifier has poor compatibility with the photoconductive substance, and also tends to act as a trap for the movement of carriers due to photogeneration, resulting in repeated electrophotographic processes. There was a tendency for the residual charge to increase. On the other hand, a surface layer in which Teflon powder or the like is dispersed has problems such as poor dispersibility, decreased transparency, and carrier trapping.
本発明は、従来の問題点を解決して、表面の潤滑性を上
げる事によりすべり抵抗を低減させ、結果的に耐摩耗性
に優れ、かつ、すべり性に優れる為トナー融着等の発生
のない電子写真感光体も提供する事を目的としている。The present invention solves the conventional problems and reduces the sliding resistance by increasing the lubricity of the surface.As a result, it has excellent wear resistance and slipperiness, which reduces the occurrence of toner fusion, etc. The purpose of the present invention is to provide an electrophotographic photoreceptor that does not require the above.
本発明の別の目的は繰返し電子写真プロセスにおいて残
留電荷の蓄積がなく、怒度に優れ常に高品位の画像が得
られる電子写真感光体を提供することにある。Another object of the present invention is to provide an electrophotographic photoreceptor that does not accumulate residual charge during repeated electrophotographic processes, has excellent stability, and can consistently produce high-quality images.
本発明は電子写真感光体の、少なくとも基体より最も離
隔する層に、特定のシリ−コン系クシ型グラフトポリマ
ーとマレインイミド系樹脂とを含有させることによって
上記目的を達成しようとするものである。The present invention aims to achieve the above object by incorporating a specific silicone-based comb-shaped graft polymer and a maleimide-based resin into at least the layer of an electrophotographic photoreceptor that is farthest from the substrate.
すなわち、本発明は一般式(I)
(式中、R+ 、Rz 、R3,R4、Rsは置換基を
有してもよいアルキル基またはアリール基を示し、nは
平均重合度を示す。)
及び/又は一般式(n)
■
HO−+ S i O+−VH(II )嘲
Rフ
(式中、R,、R,は置換基を有してもよいアルキル基
または了り−ル基を示し、nは平均重合度を示す。)
で示されるシリコーンと少な(とも一般式(nl)(式
中、Rs 、Rq 、R+。は水素原子、ハロゲン原子
、置換基を有してもよいアルキル基または了り−ル基を
示し、R11は置換基を有してもよいアルキル基または
アリール基を示し、Aは置換基を有してもよいアリーレ
ンを示し、Xはハロゲン原子、置換基を有してもよいア
ルコキシ基を示し、mは1〜3の整数を示す。)
で示される化合物との縮合反応生成物と重合性不飽和結
合含有化合物との共重合体であるシリコーン系クシ型グ
ラフトポリマーと、マレインイミド系樹脂を、少なくと
も基体より最も離隔せる層中に含有せることを特徴とす
る電子写真感光体である。That is, the present invention relates to general formula (I) (wherein R+, Rz, R3, R4, and Rs represent an alkyl group or an aryl group that may have a substituent, and n represents an average degree of polymerization) and /or general formula (n) ■ HO-+ S i O+-VH (II) , n indicates the average degree of polymerization. or R11 represents an alkyl group or an aryl group which may have a substituent, A represents an arylene which may have a substituent, and X represents a halogen atom or an aryl group which may have a substituent. (m is an integer of 1 to 3. The present invention is an electrophotographic photoreceptor characterized in that a polymer and a maleimide resin are contained at least in a layer furthest from a substrate.
以下本発明の詳細な説明する。The present invention will be explained in detail below.
電子写真感光体は、当業界で知られている様に、基体上
に感光層及び必要に応じて非感光性の下引層、中間層及
び表面層等を有し、また、前記感光層としては、単層構
造を有しているものや電荷発生層と電荷輸送層との積層
構造を有するものなどがある。本発明はこれら公知のあ
らゆるタイプの電子写真感光体として適用することがで
きるものであり、少なくとも基体より最も離隔する層(
以下、本発明に係る表面層という)として、例えば前記
非感光性の表面層、単層構造の感光層、積層構造の感光
層における電荷発生層乃至は電荷輸送層に、以下に詳述
するシリコーン系クシ型グラフトポリマーとマレインイ
ミド系樹脂とが含有されている。As is known in the art, an electrophotographic photoreceptor has a photosensitive layer on a substrate and, if necessary, a non-photosensitive subbing layer, an intermediate layer, a surface layer, etc., and as the photosensitive layer. There are those that have a single layer structure and those that have a laminated structure of a charge generation layer and a charge transport layer. The present invention can be applied to all of these known types of electrophotographic photoreceptors, and includes at least the layer furthest away from the substrate (
As the surface layer (hereinafter referred to as the surface layer according to the present invention), for example, the charge generation layer or the charge transport layer in the non-photosensitive surface layer, the photosensitive layer having a single layer structure, the photosensitive layer having a laminated structure, etc. Contains a comb-type graft polymer and a maleimide resin.
本発明で用いられるシリコーン系クシ型グラフトポリマ
ーは下記一般式(1)および/または一般式(n)で示
されるシリコンと下記一般式(III)を含む化合物と
の縮合反応生成物である変性シリコーンと重合性官能基
をもつ化合物を共重合させて得られるものであり、重合
性官能基を含有せる化合物からなる主鎖に対して変性シ
リコーンからなるシリコーンを含有する側鎖基が枝状に
結合した構造を有している。The silicone-based comb-shaped graft polymer used in the present invention is a modified silicone which is a condensation reaction product of silicone represented by the following general formula (1) and/or general formula (n) and a compound containing the following general formula (III). It is obtained by copolymerizing a compound with a polymerizable functional group, and a silicone-containing side chain group made of modified silicone is bonded in a branched manner to a main chain made of a compound containing a polymerizable functional group. It has a similar structure.
一般式(I)
但し、R+ 、Rz 、Rs 、R4、Rsは置換基を
有してもよいアルキル基またはアリール基を示し、nは
平均重合度を示す。General formula (I) However, R+, Rz, Rs, R4, and Rs represent an alkyl group or an aryl group that may have a substituent, and n represents an average degree of polymerization.
一般式(n)
HO−+ 5iOh−H
■
R1
但し、R,、Rtは置換基を有してもよいアルキル基ま
たは了り−ル基を示し、nは平均重合度を示す。General formula (n) HO-+ 5iOh-H ■R1 However, R,, Rt represent an alkyl group or an aryol group which may have a substituent, and n represents an average degree of polymerization.
一般式(I[[)
但し、Ro + R9+ Rhoは水素原子、ハロゲ
ン原子、置換基を有してもよいアルキル基またはアリー
ル基を示し、Roは置換基を有してもよいアルキル基ま
たは了り−ル基を示し、Aは置換基を有してもよいアリ
ーレンを示し、Xはハロゲン原子、置換基を有してもよ
いアルコキシ基を示し、mは1〜3の整数を示す。General formula (I[[) However, Ro + R9+ Rho represents a hydrogen atom, a halogen atom, an alkyl group or an aryl group which may have a substituent, and Ro represents an alkyl group or an aryl group which may have a substituent. A represents an arylene group which may have a substituent, X represents a halogen atom or an alkoxy group which may have a substituent, and m represents an integer of 1 to 3.
前記一般式(I)および(n)式中、R,、Rt。In the general formulas (I) and (n), R,, Rt.
R3,R,、Rs、R&およびR7は、具体的には、メ
チル、エチル、プロピル、ブチルなどのアルキル基また
はフェニル、ナフチルなどのアリール基であり、ハロゲ
ン原子、低級アルキル基などの置換基を有してもよい。Specifically, R3, R,, Rs, R&, and R7 are alkyl groups such as methyl, ethyl, propyl, and butyl, or aryl groups such as phenyl and naphthyl, and have substituents such as halogen atoms and lower alkyl groups. May have.
好ましくはメチル基、フェニル基である。Preferred are methyl group and phenyl group.
nは平均重合度を示し、1〜1000の範囲、好ましく
は10〜500の範囲である。n indicates an average degree of polymerization, and is in the range of 1 to 1000, preferably in the range of 10 to 500.
一般式(I[[)の式中、R1,R9およびR5゜は、
具体的には、水素原子、フッ素、塩素、臭素、ヨウ素な
どハロゲン原子、メチル、エチル、プロピル、ブチルな
どのアルキル基またはフェニル、ナフチルなどのアリー
ル基であり、ハロゲン原子、低級アルキル基などの置換
基を有してもよい。好ましくは水素原子である。In the general formula (I[[), R1, R9 and R5° are
Specifically, hydrogen atoms, halogen atoms such as fluorine, chlorine, bromine, and iodine, alkyl groups such as methyl, ethyl, propyl, and butyl, or aryl groups such as phenyl and naphthyl, and substitution of halogen atoms and lower alkyl groups. It may have a group. Preferably it is a hydrogen atom.
R11は、具体的には、メチル、エチル、プロピル、ブ
チルなどのアルキル基またはフェニル、ナフチルなどの
アリール基であり、ハロゲン原子などの置換基を有して
もよい。好ましくはメチル基、フェニル基である。Specifically, R11 is an alkyl group such as methyl, ethyl, propyl, butyl, or an aryl group such as phenyl or naphthyl, and may have a substituent such as a halogen atom. Preferred are methyl group and phenyl group.
Xは具体的には、水素原子、フッ素、塩素、臭素、ヨウ
素などハロゲン原子、メトキシ、エトキシ、プロポキシ
、ブトキシなどのアルコキシ基であり、低級アルコキシ
基などの置換基を有してもよい。好ましくはメトキシ基
、エトキシ基、2−メトキシ−エトキシ基である。Specifically, X is a hydrogen atom, a halogen atom such as fluorine, chlorine, bromine, or iodine, or an alkoxy group such as methoxy, ethoxy, propoxy, or butoxy, and may have a substituent such as a lower alkoxy group. Preferred are methoxy group, ethoxy group, and 2-methoxy-ethoxy group.
Aはフェニレン、ビフェニレン、ナフチレンなどのアリ
ーレン基であり、ハロゲン原子、低級アルキル基などの
置換基を有してもよい。mは1〜3の整数である。A is an arylene group such as phenylene, biphenylene, or naphthylene, and may have a substituent such as a halogen atom or a lower alkyl group. m is an integer from 1 to 3.
−a式(I)〜(III)の具体例を以下に示す。-a Specific examples of formulas (I) to (III) are shown below.
一般式(1)の具体例 CHs CHx CHx CHx CzHs C3H? C4H9CHs r CI 一般式(II)の具体例 患 CH。Specific example of general formula (1) CHs CHx CHx CHx CzHs C3H? C4H9CHs r C.I. Specific examples of general formula (II) disease CH.
26 HO−f S i Oh−Hs CH。26 HO-f S i Oh-Hs CH.
2Hs
27 HO−e S i Oh−Hs
Ct H5
C2H?
「
28 HO−+S i Oh−Hs
Cx H’r
C4Hq
29 HO−+S iOh−Hs
C4H9
H3
♂
30 HO→S i Oh−Hs
C,Hs
CH3
31HO−f S i O)−H
s
C3H?
Cz Hs
32 HO→ S i Oh−Hs
C4Hq
C4HmC1
33HO→SiO+r−H
s
04H@CII
CH’r
34 HO−+ S i Oh−HtH
sC1
H3
CZ Hs
r
■
一般式(I[[)の具体例
Br
一般式(1)および/または一般式(II)で示される
シリコーンと、構成成分として一般式(I[I)を含む
化合物との縮合反応は、通常の有機化学反応操作に従い
きわめて円滑に進行し、例えばクシ型グラフトポリマー
の合成方法が開示されている特開昭58−167606
、特開昭59−126478に従いその反応モル比や反
応条件を適当に制御する事により安定な変性シリコーン
を得ることができる。2Hs 27 HO-e Si Oh-Hs Ct H5 C2H? " 28 HO-+S i Oh-Hs Cx H'r C4Hq 29 HO-+S iOh-Hs C4H9 H3 ♂ 30 HO→S i Oh-Hs C, Hs CH3 31HO-f S i O)-H s C3H? Cz Hs 32 HO→ S i Oh-Hs C4Hq C4HmC1 33HO→SiO+r-H s 04H@CII CH'r 34 HO-+ S i Oh-HtH
sC1 H3 CZ Hs r ■ Specific example of general formula (I[[) Br Silicone represented by general formula (1) and/or general formula (II) and a compound containing general formula (I[I) as a constituent component. The condensation reaction proceeds very smoothly according to ordinary organic chemical reaction operations, and is described, for example, in JP-A-58-167606, which discloses a method for synthesizing comb-shaped graft polymers.
A stable modified silicone can be obtained by appropriately controlling the reaction molar ratio and reaction conditions according to JP-A-59-126478.
重合性官能基を有する化合物としては、ケイ素原子を持
たない重合性の単量体もしくは末端に重合性の官能基を
有する分子量が1000から10000程度の比較的低
分子量の重合体からなるマクロモノマー等が挙げられる
0重合性単量体としては、オレフィン系化合物の例とし
てエチレン、プロピレン、ブチレンの如き低分子量直鎖
状不飽和炭化水素、塩化ビニル及びフッ化ビニルの如き
ハロゲン化ビニル、酢酸ビニルの如き有機酸のビニルエ
ステル、スチレン、スチレン置換体並びにビニルピリジ
ン及びビニルナフタレンの如きその他のビニル芳香族化
合物、アクリル酸、メタクリル酸、並びにそれらのエス
テル、アミド及びアクリロニトリルを含むアクリル酸、
メタクリル酸の誘導体、N−ビニルカルバゾール、N−
ビニルピロリドン及びN−ビニルカプロラクタムの如き
N−ビニル化合物、ビニルトリエトキシシランの如きビ
ニルケイ素化合物等があげられる。ジ置換エチレンも使
用でき、その例としてフッ化ビニリデン、塩化ビニリデ
ン等をあげることができ、又無水マレイン酸、マレイン
酸及びフマル酸のエステル等もあげることができる。Compounds having a polymerizable functional group include macromonomers consisting of polymerizable monomers that do not have silicon atoms or relatively low molecular weight polymers with a molecular weight of about 1,000 to 10,000 that have a polymerizable functional group at the end. Examples of olefinic compounds include low molecular weight linear unsaturated hydrocarbons such as ethylene, propylene, and butylene, vinyl halides such as vinyl chloride and vinyl fluoride, and vinyl acetate. vinyl esters of organic acids such as styrene, styrene substitutes, and other vinyl aromatic compounds such as vinylpyridine and vinylnaphthalene; acrylic acid, including acrylic acid, methacrylic acid, and their esters, amides, and acrylonitrile;
Derivatives of methacrylic acid, N-vinylcarbazole, N-
Examples include N-vinyl compounds such as vinylpyrrolidone and N-vinylcaprolactam, and vinyl silicon compounds such as vinyltriethoxysilane. Disubstituted ethylenes can also be used, examples of which include vinylidene fluoride, vinylidene chloride, etc., as well as maleic anhydride, esters of maleic acid and fumaric acid, and the like.
特に、マレインイミド系樹脂との親和性から、アクリル
酸エステル類、メタクリル酸エステル類、スチレン系等
が好ましい。In particular, acrylic esters, methacrylic esters, styrene, etc. are preferred from the viewpoint of affinity with maleimide resins.
又、モノマーは単独又は2種類以上のモノマーを組み合
わせて使用できる。Furthermore, the monomers can be used alone or in combination of two or more types.
本発明で使用する重合性官能基を有する化合物はアクリ
ルアミド、アクリル酸、アクリロニトリル、1.3−7
’タジエン、2−クロロエチル、ビニルエーテル、メタ
クリル酸ジエチル、アミノエチル、フマル酸ジエチル、
N、Nジメチルアクリルアミド、アクリル酸エチル、エ
チレン、イソブチレン、マレイン酸、無水マレイン酸、
メタクリル酸、アクリル酸メチル、メタクリロニトリル
、メタクリル酸メチル、α−メチルスチレン、p−メチ
ルスチレン、メチルビニルケトン、フマロニトリル、プ
ロペニルエーテル、プロピレン、スチレン、四フッ化エ
チレン、酢酸ビニル、N−ビニルカルバゾール、塩化ビ
ニル、塩化ビニリデン、フッ化ビニリデン、ビニルピリ
ジン、4−ビニルピリジン、2−ビニルピロール、N−
ビニルピロリドン、N−ビニルコハク酸イミド、ビニル
スルフィド等が挙げられる。Compounds having polymerizable functional groups used in the present invention include acrylamide, acrylic acid, acrylonitrile, 1.3-7
'Tadiene, 2-chloroethyl, vinyl ether, diethyl methacrylate, aminoethyl, diethyl fumarate,
N, N dimethylacrylamide, ethyl acrylate, ethylene, isobutylene, maleic acid, maleic anhydride,
Methacrylic acid, methyl acrylate, methacrylonitrile, methyl methacrylate, α-methylstyrene, p-methylstyrene, methyl vinyl ketone, fumaronitrile, propenyl ether, propylene, styrene, tetrafluoroethylene, vinyl acetate, N-vinylcarbazole , vinyl chloride, vinylidene chloride, vinylidene fluoride, vinylpyridine, 4-vinylpyridine, 2-vinylpyrrole, N-
Examples include vinylpyrrolidone, N-vinylsuccinimide, vinyl sulfide, and the like.
シリコーン系クシ型グラフトポリマーの重合法としては
溶液重合法、懸濁重合法、バルク重合法等のラジカル重
合やイオン重合が適用できるが、溶液重合法によるラジ
カル重合が筒便で好ましい。Radical polymerization and ionic polymerization such as solution polymerization, suspension polymerization, and bulk polymerization can be used as the polymerization method for silicone-based comb-shaped graft polymers, but radical polymerization by solution polymerization is preferred.
共重合比はシリコーン系単量体の含有率として5〜90
重量%が好ましく、10〜70重世%が更に好ましい。The copolymerization ratio is 5 to 90 as the silicone monomer content.
% by weight is preferred, and 10 to 70 weight % is more preferred.
得られた重合体の分子量は数平均分子量として500か
ら100000、特に1000から50000が好まし
い。The number average molecular weight of the obtained polymer is preferably 500 to 100,000, particularly preferably 1,000 to 50,000.
本発明におけるシリコーン系クシ型グラフトポリマーは
かかる構造を有しているので本発明に係る表面層形成用
のバインダー樹脂として、マレインイミド系樹脂を含有
する塗工液に対する相溶性がすぐれており、従って得ら
れる塗膜は良好な透明性を有し、かつ本発明に係る表面
層上への移行ないし滲み出しをおこすことなく効果の持
続性を有するものであり、またシリコーン含有の技の部
分は界面移行性がすぐれているので少量の添加により表
面の改質が達成される。更にこの添加剤を表面層に含有
させてもくり返し電子写真プロセスによる残留電荷の蓄
積がなく安定した帯電特性が得られる。Since the silicone-based comb-shaped graft polymer of the present invention has such a structure, it has excellent compatibility with a coating solution containing a maleimide-based resin as a binder resin for forming a surface layer according to the present invention, and therefore The resulting coating film has good transparency and has a long-lasting effect without causing any migration or oozing onto the surface layer according to the present invention, and the silicone-containing part has no interface. Since it has excellent migration properties, surface modification can be achieved by adding a small amount. Furthermore, even when this additive is included in the surface layer, stable charging characteristics can be obtained without the accumulation of residual charges due to repeated electrophotographic processes.
本発明で用いられるマレインイミド系樹脂は、下記一般
式(IV)で示される繰り返し単位の1種又は2種以上
を成分とするポリマーを含有するものである。The maleimide resin used in the present invention contains a polymer containing one or more repeating units represented by the following general formula (IV).
一般式(IV)
(式中R,−R,は水素原子、フェニル基、置換基を有
してもよいアルキル基、またはアリール基を示し、nは
平均重合度を示す。)
本発明に用いられるマレインイミド系樹脂は、下記一般
式(V)で示されるマレインイミド化合物とオレフィン
類、ビニル化合物類、アクリル酸化合物類等重合性官能
基を有する化合物とを共重合させる事によって得られる
。General formula (IV) (In the formula, R and -R represent a hydrogen atom, a phenyl group, an alkyl group that may have a substituent, or an aryl group, and n represents an average degree of polymerization.) Used in the present invention The maleimide resin can be obtained by copolymerizing a maleimide compound represented by the following general formula (V) with a compound having a polymerizable functional group such as an olefin, a vinyl compound, or an acrylic acid compound.
一般式(V) R,R。General formula (V) R,R.
+1 C= C o=c c=。+1 C= C o=c c=.
(式中R1,R1,R,は水素原子、フェニル基、置換
基を有してもよいアルキル基、またはアリール基)
一般式(V)で示される具体例を構造式で示す。(In the formula, R1, R1, and R are a hydrogen atom, a phenyl group, an alkyl group that may have a substituent, or an aryl group) Specific examples represented by general formula (V) are shown as structural formulas.
H C= C I H CHzCHz CH。H C= C I H ChzChz CH.
H
CHtG HzC1
■
CH3
N
■
Hx
本発明に用いられるマレインイミド系樹脂を得る方法は
前記一般式(V)で示されるマレインイミド化合物の1
種あるいは2種以上と前記重合性官能基を有する化合物
の1種あるいは2種以上とを共重合せしめる事により得
る事ができる。H CHtG HzC1 ■ CH3 N ■ Hx The method for obtaining the maleimide resin used in the present invention is to obtain one of the maleimide compounds represented by the general formula (V) above.
It can be obtained by copolymerizing one or more species with one or more compounds having a polymerizable functional group.
重合方法としては、溶液重合法、懸濁重合法、バルク重
合法等のラジカル重合やイオン重合が適用できるが、溶
液重合法によるラジカル重合が簡便であり好ましい。As the polymerization method, radical polymerization and ionic polymerization such as solution polymerization, suspension polymerization, and bulk polymerization can be applied, but radical polymerization by solution polymerization is simple and preferred.
本発明においては、マレインイミドの含有率は共重合体
の5%以上特に10〜70%が好ましく得られた重合体
の分子量は重量平均分子量MWで10.000〜i 、
ooo 、 ooo特に100.000〜600,0
00が好ましい。In the present invention, the content of maleimide in the copolymer is preferably 5% or more, particularly 10 to 70%, and the molecular weight of the obtained polymer is 10.000 to i in terms of weight average molecular weight MW.
ooo, ooo especially 100.000~600.0
00 is preferred.
シリコーン系クシ型グラフトポリマーの添加量は表面層
の固形分重量にもとづいて0.01〜10%が適当であ
り、特に0.05〜5%が好ましい。The amount of the silicone comb-shaped graft polymer added is suitably 0.01 to 10%, particularly preferably 0.05 to 5%, based on the solid weight of the surface layer.
添加量が0.01%未満では十分な表面改質効果が得ら
れず、一方10%を、こえるとグラフトポリマーが塗膜
表面だけでなくバルク中にも存在するようになるため表
面層の主成分である樹脂や光導電性物質との相溶性の問
題から白化をひきおこしたり、繰返し電子写真プロセス
を行なったとき残留電荷の蓄積が生じてくる。If the amount added is less than 0.01%, a sufficient surface modification effect cannot be obtained, while if it exceeds 10%, the graft polymer will exist not only on the surface of the coating film but also in the bulk, so that it will not be the main component of the surface layer. Problems with compatibility with the component resins and photoconductive substances can cause whitening, and residual charges can accumulate when electrophotographic processes are repeated.
以下、感光層が電荷発生層と電荷輸送層との積層構造を
有し、本発明に係る表面層が電荷輸送層である場合を例
にとり、本発明の詳細な説明する。The present invention will be described in detail below, taking as an example the case where the photosensitive layer has a laminated structure of a charge generation layer and a charge transport layer, and the surface layer according to the present invention is the charge transport layer.
本発明の電子写真感光体を製造する場合、基体としては
、アルミニウム、ステンレスなどの金属、紙、プラスチ
ックなどの円筒状シリンダーまたはフィルムが用いられ
る。これらの基体の上には、バリアー機能と下引機能を
もつ下引層(接着層)を設けることができる。When producing the electrophotographic photoreceptor of the present invention, a cylindrical cylinder or film made of metal such as aluminum or stainless steel, paper, or plastic is used as the substrate. A subbing layer (adhesive layer) having a barrier function and a subbing function can be provided on these substrates.
下引層は感光層の接着性改良、塗工性改良、基体の保護
、基体上の欠陥の被覆、基体からの電荷注入性改良、感
光層の電気的破壊に対する保護などのために形成される
。下引層の材料としては、ポリビニルアルコール、ポリ
−N−ビニルイミダゾール、ポリエチレンオキシド、エ
チルセルロース、メチルセルロース、エチレン−アクリ
ル酸コポリマー、カゼイン、ポリアミド、共重合ナイロ
ン、ニカワ、ゼラチン、等が知られている。これらはそ
れぞれに適した溶剤に溶解されて基体上に塗布される。The undercoat layer is formed to improve adhesion of the photosensitive layer, improve coating properties, protect the substrate, cover defects on the substrate, improve charge injection from the substrate, protect the photosensitive layer from electrical breakdown, etc. . Known materials for the undercoat layer include polyvinyl alcohol, poly-N-vinylimidazole, polyethylene oxide, ethyl cellulose, methyl cellulose, ethylene-acrylic acid copolymer, casein, polyamide, copolymerized nylon, glue, gelatin, and the like. These are each dissolved in a suitable solvent and applied onto the substrate.
その膜厚は0.2〜2μ程度である。The film thickness is about 0.2 to 2μ.
機能分離型感光体においては、電荷発生物質としてセレ
ン、セレン−テルル、ピリリウム、チオピリリウム系染
料、フタロシアニン系顔料アントアントロン顔料、ジベ
ンズピレンキノン顔料、とラントロン顔料、トリスアゾ
顔料、ジスアゾ顔料、アゾ顔料、インジゴ顔料、キナク
リドン系顔料、非対称キノシアニン、キノシアニンある
いは特開昭54−143645号公報に記載のアモルフ
ァスシリコンなどを用いることができ、電荷輸送物質と
しては、ピレン、N−エチルカルバゾール、N−イソプ
ロピルカルバゾール、N−メチル−N−フェニルヒドラ
ジノ−3−メチリデン−9−エチルカルバゾール、N、
N−ジフェニルヒドラジノ−3−メチリデン−9−エチ
ルカルバゾール、N、N−ジフェニルヒドラジノ−3−
メチリデン−10−エチルフェノチアジン、N、N−ジ
フェニルヒドラジノ−3−メチリデン−10−エチルフ
ェノキサジン、p−ジエチルアミノベンズアルデヒド−
N、N−ジフェニルヒドラゾン、p−ジエチルアミノベ
ンズアルデヒド−N−α−ナフチル−N−フェニルヒド
ラジノ、p−ピロリジノベンズアルデヒド−N、N−ジ
フェニルヒドラゾン、1,3.3− )ジメチルインド
レニン−ω−アルデヒド−N、N−ジフェニルヒドラゾ
ン、p−ジエチルベンズアルデヒド−3−メチルベンズ
チアゾリノン−2−ヒドラゾン等のヒドラゾン類、2,
5−ビス(p−ジエチルアミノフェニル”)−1,3,
4−オキサジアゾール、l−フェニル−3−(p−ジエ
チルアミノスチリル)−5−(p−ジエチルアミノフェ
ニル)ビラプリン、1−〔キノリル(21〕−3−(p
−ジエチルアミノスチリル)−5−(p−ジエチルアミ
ノフェニル)ピラゾリン、1−〔ピリジル(2))−3
−(p−ジエチルアミノスチリル)−5−(p−ジエチ
ルアミノフェニル)ピラゾリン、1−〔6−メドキシー
ビリジル(2)) −3−(p−ジエチルアミノスチリ
ル)−5−(p−ジエチルアミノフェニル)ピラゾリン
、1−〔ピリジル(3))−3−(p−ジエチルアミノ
スチリル)−5−(p−ジエチルアミノフェニル)ピラ
ゾリン、1−〔レビジルfzl) −3−(p−ジエチ
ルアミノスチリル)−5−(p−ジエチルアミノフェニ
ル)ピラゾリン、1−〔ピリジル(2)) −3−(p
−ジエチルアミノスチリル)−4−メチル−5−(p−
ジエチルアミノフェニル)ピラゾリン、■−〔ピリジル
(2))−3−(α−メチル−p−ジエチルアミノスチ
リル)−5(p−ジエチルアミノフェニル)ピラゾリン
、1−フェニル−3−(p−ジエチルアミノスチリル)
−4−メチル−5−(p−ジエチルアミノフェニル)ピ
ラゾリン、1−フェニル−3−(α−ベンジル−p−ジ
エチルアミノスチリル)−5(p−ジエチルアミノフェ
ニル)ピラゾリン、スピロピラゾリンなどのピラゾリン
類、2− (p−ジエチルアミノスチリル)−6−シエ
チルアミノベンズオキサゾール、2−(p−ジエチルア
ミノフェニル)−4−(p−ジメチルアミノフェニル)
−5−、(2−クロロフェニル)オキサゾール等のオキ
サゾール系化合物、2−(p−ジエチルアミノスチリル
)−6−シエチルアミノベンズオキサゾール等のチアゾ
ール系化合物、ビス(4−ジエチルアミノ−2−メチル
フェニル)−フェニルメタン等のトリアリールメタン系
化合物、1.1−ビス(4−N、N−ジエチルアミノ−
2−メチルフェニル)へブタン、1.1.2.2−テト
ラキス(4−N、N−ジメチルアミノ−2−メチルフェ
ニル)エタン等のポリアリールアルカン類などを用いる
ことができる。In the functionally separated photoreceptor, the charge generating substances include selenium, selenium-tellurium, pyrylium, thiopyrylium dyes, phthalocyanine pigments, anthoanthrone pigments, dibenzpyrenequinone pigments, lanthrone pigments, trisazo pigments, disazo pigments, azo pigments, Indigo pigments, quinacridone pigments, asymmetric quinocyanine, quinocyanine, or the amorphous silicon described in JP-A-54-143645 can be used, and as the charge transport substance, pyrene, N-ethylcarbazole, N-isopropylcarbazole, N-methyl-N-phenylhydrazino-3-methylidene-9-ethylcarbazole, N,
N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-
Methylidene-10-ethylphenothiazine, N,N-diphenylhydrazino-3-methylidene-10-ethylphenoxazine, p-diethylaminobenzaldehyde
N,N-diphenylhydrazone, p-diethylaminobenzaldehyde-N-α-naphthyl-N-phenylhydrazino, p-pyrrolidinobenzaldehyde-N,N-diphenylhydrazone, 1,3.3-)dimethylindolenine-ω- Hydrazones such as aldehyde-N,N-diphenylhydrazone, p-diethylbenzaldehyde-3-methylbenzthiazolinone-2-hydrazone, 2,
5-bis(p-diethylaminophenyl")-1,3,
4-Oxadiazole, l-phenyl-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl) birapurine, 1-[quinolyl(21)]-3-(p
-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[pyridyl(2))-3
-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[6-medoxybilidyl (2)) -3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline , 1-[Pyridyl(3))-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[Levidyl fzl)-3-(p-diethylaminostyryl)-5-(p- diethylaminophenyl)pyrazoline, 1-[pyridyl (2)) -3-(p
-diethylaminostyryl)-4-methyl-5-(p-
diethylaminophenyl)pyrazoline, ■-[pyridyl(2))-3-(α-methyl-p-diethylaminostyryl)-5(p-diethylaminophenyl)pyrazoline, 1-phenyl-3-(p-diethylaminostyryl)
Pyrazolines such as -4-methyl-5-(p-diethylaminophenyl)pyrazoline, 1-phenyl-3-(α-benzyl-p-diethylaminostyryl)-5(p-diethylaminophenyl)pyrazoline, spiropyrazoline, 2-( p-diethylaminostyryl)-6-ethylaminobenzoxazole, 2-(p-diethylaminophenyl)-4-(p-dimethylaminophenyl)
Oxazole compounds such as -5-, (2-chlorophenyl)oxazole, thiazole compounds such as 2-(p-diethylaminostyryl)-6-ethylaminobenzoxazole, bis(4-diethylamino-2-methylphenyl)- Triarylmethane compounds such as phenylmethane, 1,1-bis(4-N,N-diethylamino-
Polyarylalkanes such as 2-methylphenyl)hebutane and 1.1.2.2-tetrakis(4-N,N-dimethylamino-2-methylphenyl)ethane can be used.
電荷発生層は、前記の電荷発生物質を0.3〜4倍量の
結着剤樹脂、および溶剤と共に、ホモジナイザー、超音
波、ボールミル、振動ボールミル、サンドミル、アトラ
イター、ロールミルなどの方法でよく分散し、塗布−乾
燥されて形成される。The charge generation layer is prepared by dispersing the above charge generation substance together with 0.3 to 4 times the amount of a binder resin and a solvent using a method such as a homogenizer, ultrasonic waves, a ball mill, a vibrating ball mill, a sand mill, an attritor, or a roll mill. It is formed by coating and drying.
その厚みは0.1〜1μ程度である。Its thickness is about 0.1 to 1 μm.
電荷輸送層は本9発明に係るマレインイミド系樹脂とシ
リコーン系クシ型グラフトポリマーとを結着剤として電
荷輸送物質と共に溶剤に溶解し、電荷発生層上に塗布さ
れる。電荷輸送物質と結着剤樹脂との混合割合は2:1
〜1:2程度である。The charge transport layer is formed by dissolving a maleimide resin according to the present invention and a silicone comb-shaped graft polymer as a binder in a solvent together with a charge transport substance, and coating the mixture on the charge generation layer. The mixing ratio of charge transport material and binder resin is 2:1
The ratio is about 1:2.
溶剤としては、アセトン、メチルエチルケトンなどのケ
トン類、酢酸メチル、酢酸エチルなどのエステル類、ト
ルエン、キシレンなどの芳香族炭化水素類、クロルベン
ゼン、クロロホルム、四塩化炭素などの塩素系炭化水素
類などが用いられる。Examples of solvents include ketones such as acetone and methyl ethyl ketone, esters such as methyl acetate and ethyl acetate, aromatic hydrocarbons such as toluene and xylene, and chlorinated hydrocarbons such as chlorobenzene, chloroform, and carbon tetrachloride. used.
この溶液を塗布する際には、例えば浸漬コーティング法
、スプレーコーティング法、スピンナーコーティング法
、ビードコーティング法、ブレードコーティング法、カ
ーテンコーティング法などのコーティング法を用いるこ
とができ、乾燥は10℃〜200℃、好ましくは20℃
〜150℃の範囲の温度で5分〜5時間、好ましくは1
0分〜2時間の時間で送風乾燥または静止乾燥下で行な
うことができる。生成した電荷輸送層の膜厚は5〜20
μ程度である。When applying this solution, coating methods such as dip coating, spray coating, spinner coating, bead coating, blade coating, and curtain coating can be used, and drying is carried out at 10°C to 200°C. , preferably 20°C
5 minutes to 5 hours at a temperature in the range of ~150°C, preferably 1
The drying can be carried out for 0 minutes to 2 hours under blow drying or stationary drying. The thickness of the generated charge transport layer is 5 to 20
It is about μ.
また、電荷輸送層には、種々の添加剤を含有させること
ができる。かかる添加剤としては、ジフェニル、塩化ジ
フェニル、〇−ターフェニル、p−ターフェニル、ジブ
チルフタレート、ジメチルグリコールフタレート、ジオ
クチルフタレート、トリフェニル燐酸、メチルナフタリ
ン、ベンゾフェノン、塩素化パラフィン、ジラウリルチ
オプロピオネート、3,5−ジニトロサリチル酸、各種
フルオロカーボン類などを挙げることができる。Further, the charge transport layer can contain various additives. Such additives include diphenyl, diphenyl chloride, 0-terphenyl, p-terphenyl, dibutyl phthalate, dimethyl glycol phthalate, dioctyl phthalate, triphenyl phosphoric acid, methylnaphthalene, benzophenone, chlorinated paraffin, dilaurylthiopropionate. , 3,5-dinitrosalicylic acid, and various fluorocarbons.
一方、電荷発生層を表面層とする機能分離型感光体では
本発明に係るマレインイミド系樹脂とシリ−コン系クシ
型グラフトポリマーとを電荷発生物質の結着剤として用
いることができる。On the other hand, in a functionally separated photoreceptor having a charge generation layer as a surface layer, the maleimide resin and the silicone comb-shaped graft polymer according to the present invention can be used as a binder for a charge generation substance.
更に、感光層を本発明に係る表面層とする単層型感光体
においてもマレインイミド系樹脂とシリ−コン系クシ型
グラフトポリマーとを結着剤として感光層に用いること
ができ、又感光体表面に非感光性の表面層を例えば保護
層として設ける場合、本発明に係るマレインイミド系樹
脂とシリコーン系クシ型ポリマーを保護膜形成材料とし
て用いることができる。Furthermore, even in a single-layer type photoreceptor in which the photoreceptor layer is the surface layer according to the present invention, a maleimide resin and a silicone-based comb-shaped graft polymer can be used as a binder in the photoreceptor layer. When a non-photosensitive surface layer is provided on the surface, for example, as a protective layer, the maleimide resin and silicone comb-shaped polymer according to the present invention can be used as the material for forming the protective film.
以下、本発明を実施例に従って説明する。Hereinafter, the present invention will be explained according to examples.
以下の実施例で用いたシリ−コン系クシ型グラフトポリ
マー(試料Na a w o )はクシ型グラフトポリ
マーの合成方法が開示されている特開昭58−1676
06、特開昭59−126478に準じて前記一般式(
I)および/または前記一般式(II)で示されるシリ
コーンと少なくとも前記一般式(I[[)との縮合反応
生成物である変性シリコーンとラジカル重合性モノマー
をラジカル共重合して合成したものであり、その組成は
表1に示す如くである。The silicone-based comb-shaped graft polymer (sample Na w o ) used in the following examples is based on Japanese Patent Application Laid-Open No. 58-1676, which discloses a method for synthesizing a comb-shaped graft polymer.
06, the above general formula (
I) and/or a modified silicone which is a condensation reaction product of the silicone represented by the above general formula (II) and at least the above general formula (I[[), and a radically polymerizable monomer synthesized by radical copolymerization. The composition is shown in Table 1.
合成したシリコーン型グラフトポリマーの構造を、試料
Naaおよびhについて代表例として以下に示す。The structures of the synthesized silicone-type graft polymers are shown below as representative examples for samples Naa and h.
試料a
n:平均:30
9貫・ q■ :正の整数
A、/Bl : 30/70 (重量比)試料h
A t B tn:平均:30
ptr qt’正の整数
At /B! : 30/70 (重量比)実施例1
ニューシーラント産うクチックカゼインを10部(重量
部、以下同様)計りとり、水90部に分散させた後、ア
ンモニア水1部を加えて溶解させた。一方、ヒドロキシ
プロピルメチルセルロース樹脂(商品名:メトローズ6
0SH50、信越化学製)3部を水20部に溶解させ、
次いで両者を混合して下引き層の塗布液を作った。Sample a n: Average: 30 9 pieces q■: Positive integer A, /Bl: 30/70 (weight ratio) Sample h A t B tn: Average: 30 ptr qt' Positive integer At /B! : 30/70 (weight ratio) Example 1 10 parts (parts by weight, the same applies hereinafter) of cutic casein produced by New Sealant were weighed out, dispersed in 90 parts of water, and then dissolved by adding 1 part of aqueous ammonia. . On the other hand, hydroxypropyl methylcellulose resin (product name: Metrose 6)
Dissolve 3 parts of 0SH50 (manufactured by Shin-Etsu Chemical) in 20 parts of water,
Next, the two were mixed to prepare a coating solution for an undercoat layer.
この液を80φX 3 Q O*mのへ1シリンダーに
浸漬法で塗布し、80℃で10分間乾燥させ、2μ厚の
下引き層を形成した。This liquid was applied to one cylinder of 80φX 3 QO*m by dipping method and dried at 80° C. for 10 minutes to form an undercoat layer with a thickness of 2 μm.
次に下記構造式のジスアゾ顔料を10部酢酸酪酸セルロ
ース樹脂(商品名: CA B −381:イーストマ
ン化学製)6部およびシクロヘキサノン60部をlφガ
ラスピーズを用いたサンドミル装置で20時間分散した
。この分散液にメチルオチルケトン100部を加えて、
上記下引層上に浸漬塗布し、100℃で10分間の加熱
乾燥をして、0.1g/rdの塗布量の電荷発生層をも
うけた。Next, 10 parts of a disazo pigment having the following structural formula, 6 parts of cellulose acetate butyrate resin (trade name: CA B-381, manufactured by Eastman Chemical Co., Ltd.) and 60 parts of cyclohexanone were dispersed for 20 hours using a sand mill apparatus using lφ glass beads. Add 100 parts of methyl ethyl ketone to this dispersion,
It was applied by dip coating onto the above-mentioned undercoat layer and dried by heating at 100° C. for 10 minutes to form a charge generation layer with a coating weight of 0.1 g/rd.
次いで、下記構造式のヒドラゾン化合物を10部、
一般式(V)の具体例光123のフェニルマレインイミ
ドとメタクリル酸メチルとを共重合せしめた樹脂10部
をジクロロメタン100部に溶解した。この液に試料1
1kLaシリコーン系クシ型グラフトポリマーを固形分
として0.2部加えた。この溶液を上記電荷発生層上に
塗布し100℃1時間熱風乾燥して16μ厚の電荷輸送
層を形成した。Next, 10 parts of a hydrazone compound having the following structural formula and 10 parts of a resin obtained by copolymerizing phenylmaleimide and methyl methacrylate of Specific Example Hikari 123 of the general formula (V) were dissolved in 100 parts of dichloromethane. Add sample 1 to this solution.
0.2 part of a 1 kLa silicone comb-shaped graft polymer was added as a solid content. This solution was applied onto the charge generation layer and dried with hot air at 100° C. for 1 hour to form a charge transport layer with a thickness of 16 μm.
これを試料1とする。同様に試料Nl b w oのシ
リコーン系クシ型グラフトポリマーを用いて調製した電
子写真感光体を試料2〜15とする。This is designated as sample 1. Electrophotographic photoreceptors similarly prepared using the silicone-based comb-shaped graft polymer of Sample Nl b w o are designated as Samples 2 to 15.
比較のためシリコーン系クシ型グラフトポリマーを添加
しないものを上記と同様にして作成した。For comparison, a sample without the silicone comb-shaped graft polymer was prepared in the same manner as above.
これらを試料16とする。These will be referred to as sample 16.
これらの試料に対し、−5,5kV、コロナ帯電、画像
露光、乾式トナー現像、普通紙へのトナー転写、ウレタ
ンゴムブレードによるクリーニングからなる電子写真プ
ロセスにて5000枚の耐久性評価を行なった。その結
果を下記表1に示した。The durability of these samples was evaluated on 5,000 sheets using an electrophotographic process consisting of -5.5 kV, corona charging, image exposure, dry toner development, toner transfer to plain paper, and cleaning with a urethane rubber blade. The results are shown in Table 1 below.
表 1
実施例2
実施例1で用いたヒドラゾン化合物10部及び一般式(
、V)の具体例N1124のメチルマレインイミドスチ
レンとを共重合せしめた樹脂10部をモノクロルベンゼ
ン80部に溶解した。この液に試料mhのシリコーン系
クシ型グラフI・ポリマーを固形分として0.4部加え
た。この溶液を実施例1と同様にして作成した電荷発生
層まで塗工した基体上に塗布し、100℃1時間熱風乾
燥して16μ厚の電荷輸送層を形成した。これを試料1
7とする。Table 1 Example 2 10 parts of the hydrazone compound used in Example 1 and the general formula (
, 10 parts of the resin copolymerized with methylmaleimidostyrene of Specific Example N1124 of V) was dissolved in 80 parts of monochlorobenzene. To this liquid, 0.4 part of silicone comb-shaped graph I polymer of sample mh was added as solid content. This solution was applied onto a substrate coated up to the charge generation layer prepared in the same manner as in Example 1, and dried with hot air at 100° C. for 1 hour to form a charge transport layer with a thickness of 16 μm. This is sample 1
Set it to 7.
比較のためシリコーン系クシ型グラフトポリマーを添加
しないものを上記と同様にして作成した。For comparison, a sample without the silicone comb-shaped graft polymer was prepared in the same manner as above.
これを試料18とする。This is designated as sample 18.
これらの試料を実施例1と同一の条件下で耐久性評価を
行なった。その結果を表2に示す。The durability of these samples was evaluated under the same conditions as in Example 1. The results are shown in Table 2.
表 2
実施例3
80φ×300璽lのアルミニウムシリンダを基体とし
これにポリアミド樹脂(商品名:アミランCN−800
0、東し製)の5%メタ−ノール溶液を浸漬法で塗布し
、1μ厚の下引き層をもうけた。Table 2 Example 3 An aluminum cylinder of 80φ x 300 liters was used as a base, and polyamide resin (product name: Amilan CN-800
A 5% methanol solution of 0.0 (manufactured by Toshi Co., Ltd.) was applied by a dipping method to form a 1 μm thick undercoat layer.
次に下記構造式のピラゾリン化合物12部と実施例2で
合成したマレインイミド系樹脂10部をモノクロルベン
ゼン60部に溶解した。Next, 12 parts of a pyrazoline compound having the following structural formula and 10 parts of the maleimide resin synthesized in Example 2 were dissolved in 60 parts of monochlorobenzene.
この液を上記下引き層上に浸漬塗布し100℃、1時間
の乾燥をして14μの電荷輸送層を形成した。This liquid was dip coated onto the undercoat layer and dried at 100° C. for 1 hour to form a charge transport layer with a thickness of 14 μm.
次に下記構造式のビスアゾ顔料10部を実施例1で合成
したマレインイミド系樹脂の10wt%ジオキサン溶液
100部の中へ加え、ガラスピーズを用いたサンドミル
装置で20時間分散した。この分散液に試料ll&lc
のシリコーン系クシ型グラフトポリマーを固形分として
1部加えた。この溶液を電荷輸送層上に突き上げ塗布し
100℃20分間乾燥して2μ厚の電荷発生層を形成し
た。Next, 10 parts of a bisazo pigment having the following structural formula was added to 100 parts of a 10 wt% dioxane solution of the maleimide resin synthesized in Example 1, and dispersed for 20 hours using a sand mill apparatus using glass beads. Samples ll & lc were added to this dispersion.
One part of silicone-based comb-shaped graft polymer was added as a solid content. This solution was applied onto the charge transport layer and dried at 100° C. for 20 minutes to form a charge generation layer with a thickness of 2 μm.
これを試料19とする。比較のためシリコーン系クシ型
グラフトポリマーを加えない試料を上記と同様にして作
成した。これを試料20とする。This is designated as sample 19. For comparison, a sample without the silicone comb-shaped graft polymer was prepared in the same manner as above. This is designated as sample 20.
こうして得られた試料を+5.6kVコロナ帯電、画像
露光、乾式トナー現像、普通紙へのトナー転写、ウレタ
ンゴムブレード、によるクリーニング工程等を有する電
子写真複写機に取りつけて、32.5℃、RH90%の
環境にて3000枚の耐久性評価を行った。その結果を
表3に示す。The sample thus obtained was attached to an electrophotographic copying machine having +5.6 kV corona charging, image exposure, dry toner development, toner transfer to plain paper, cleaning process using a urethane rubber blade, etc., at 32.5°C and RH90. Durability evaluation was conducted on 3000 sheets in an environment of 30%. The results are shown in Table 3.
表 3
実施例4
実施例1で用いたヒドラゾン化合物10部と実施例2で
合成したマレインイミド系樹脂10部をモノクロルベン
ゼン60部に溶解した。実施例3と同様にして形成した
下引き層上にこの溶液を浸漬塗布し100℃、1時間の
乾燥をして15μの電荷輸送層を形成した。Table 3 Example 4 10 parts of the hydrazone compound used in Example 1 and 10 parts of the maleimide resin synthesized in Example 2 were dissolved in 60 parts of monochlorobenzene. This solution was applied by dip coating onto the undercoat layer formed in the same manner as in Example 3, and dried at 100° C. for 1 hour to form a charge transport layer with a thickness of 15 μm.
次に実施例3で用いたビスアゾ顔料10部を実施例2で
合成したマレインイミド系樹脂10−t%のモノクロル
ベンゼン溶液100部の中へ加えガラスピーズを用いた
サンドミル装置で20時間分散した。この分散液に試料
Nnjシリコーン系クシ型グラフトポリマーを固形分と
して1部加えた。Next, 10 parts of the bisazo pigment used in Example 3 was added to 100 parts of a monochlorobenzene solution containing 10-t% of the maleimide resin synthesized in Example 2, and dispersed for 20 hours using a sand mill apparatus using glass beads. One part of sample Nnj silicone-based comb-shaped graft polymer was added as a solid content to this dispersion.
この溶液を電荷輸送層上に突き上げ塗布し100’C2
0分間乾燥して、2.5μ厚の電荷発生層を形成した。This solution was pushed up and applied onto the charge transport layer at 10'C2.
After drying for 0 minutes, a charge generation layer having a thickness of 2.5 μm was formed.
これを試料21とする。比較のためシリコーン系クシ型
グラフトポリマーを加えない試料を上記と同様にして作
成した。これを試料22とする。This is designated as sample 21. For comparison, a sample without the silicone comb-shaped graft polymer was prepared in the same manner as above. This is designated as sample 22.
これらの試料を実施例3と同一の条件下で耐久性評価を
行なった。その結果を表4に示す。The durability of these samples was evaluated under the same conditions as in Example 3. The results are shown in Table 4.
表 2
実施例5
実施例1で合成したマレインイミド系樹脂2部をジクロ
ルメタン100部に溶解した。この溶液に試料IVhe
のシリコーン系クシ型グラフトポリマーを固形分で0.
15部加えた。この溶液を実施例1の試料6と同様に作
成した電子写真感光体の上にスプレー塗布し、100°
C5分乾燥させて0.5μの保護層を形成した。これを
試料23とする。Table 2 Example 5 Two parts of the maleimide resin synthesized in Example 1 were dissolved in 100 parts of dichloromethane. Add sample IVhe to this solution.
of silicone-based comb-shaped graft polymer with a solid content of 0.
Added 15 parts. This solution was spray applied onto an electrophotographic photoreceptor prepared in the same manner as Sample 6 of Example 1, and
It was dried for C5 minutes to form a 0.5 μm protective layer. This is designated as sample 23.
同様に実施例2で合成したマレインイミド系樹脂2部を
モノクロルベンゼン100部にm 解し、さらに試料N
utのシリコーン系クシ型グラフトポリマーを固形分で
0.5部加えた。この溶液を実施例2の試料18と同様
に作成した電子写真感光体の上にスプレー塗布し、10
0°C5分乾燥させて0.4μの保護層を形成した。こ
れを試料24とする。これらの試料を実施例1と同様の
条件下で3000枚の耐久性評価を行なった。その結果
を表5に示す。Similarly, 2 parts of the maleimide resin synthesized in Example 2 was dissolved in 100 parts of monochlorobenzene, and sample N
A solid content of 0.5 part of a silicone comb-shaped graft polymer of UT was added. This solution was spray-coated onto an electrophotographic photoreceptor prepared in the same manner as Sample 18 of Example 2.
It was dried at 0°C for 5 minutes to form a 0.4μ protective layer. This is designated as sample 24. The durability of 3000 sheets of these samples was evaluated under the same conditions as in Example 1. The results are shown in Table 5.
表 5
比較例
シリコーン系クシ型グラフトポリマーの代わりにシリコ
ーンオイル(商品名KF96信越シリコーン■製)を固
形分として1.0部を用いたほかは実施例1と同様に作
成した試料を試料25とする。Table 5 Comparative Examples Samples prepared in the same manner as in Example 1 were used as Sample 25, except that 1.0 part of silicone oil (trade name: KF96 manufactured by Shin-Etsu Silicone ■) was used as a solid content in place of the silicone-based comb-shaped graft polymer. do.
同様に上記のシリコーンオイル1.0部を用いるほかは
実施例4と同様に作成した試料を試料26とする。これ
らの試料を実施例1及び3と同様の条件下で耐久性評価
を行なったが、他力ブリがはなはだしく、更にくり返し
コピーによってカブリの度合が大きくなった。また試料
25.26を作成して1か月後に観察するとシリコーン
オイルが表面層に移行し、しみ状に浮き出ていた。一方
、シリコーン系クシ型グラフトポリマーを添加した試料
1〜15,17,19.21,23.24にはこの様な
経時変化は認められず、初期と同様の外観、特性を示し
た。Sample 26 is a sample prepared in the same manner as in Example 4, except that 1.0 part of the above silicone oil was used. Durability evaluation of these samples was carried out under the same conditions as in Examples 1 and 3, but there was a significant amount of blurring due to external forces, and the degree of fogging increased due to repeated copying. Further, when Samples 25 and 26 were observed one month after they were prepared, it was found that the silicone oil had migrated to the surface layer and stood out in the form of a stain. On the other hand, such changes over time were not observed in Samples 1 to 15, 17, 19.21, and 23.24 to which silicone-based comb-shaped graft polymers were added, and they exhibited the same appearance and characteristics as the initial stage.
実施例6
次に試料N11.17.25について−5,5kVコロ
ナ帯電器を有する電子写真複写機に取り付けて常温、常
温下5000枚の空帯電耐久試験を行ない、■。電位並
びに7.5ルツクス、秒置光させたVL電位の変動を測
定した。結果を表6に示す。Example 6 Sample N11.17.25 was then attached to an electrophotographic copying machine equipped with a -5.5 kV corona charger and subjected to an empty charging durability test of 5,000 copies at room temperature. The potential and the variation in the VL potential after 7.5 lux of seconds were measured. The results are shown in Table 6.
表 6
上表に示す様にシリコーンオイルを添加した試料の50
00枚耐久後のvL変動は非常に大きい。Table 6 50% of the sample with silicone oil added as shown in the table above
The vL fluctuation after 00 sheets durability is very large.
それに対し本発明品は耐久時の電位が極めて安定してい
ることがわかる。In contrast, it can be seen that the product of the present invention has an extremely stable potential during durability.
実施例7
次に試料1111121及び26について、+5.5k
Vコロナ帯電器を存する電子写真機に取り付けて常温、
常温下、3000枚の空帯電耐久試験を行ない、Vo電
位及び7.5ルツクス、秒置光させvL電位の変動を測
定した。結果を表7に示す。Example 7 Next, for samples 1111121 and 26, +5.5k
Attach it to an electrophotographic camera equipped with a V corona charger and leave it at room temperature.
An empty charging durability test was conducted on 3,000 sheets at room temperature, and fluctuations in the Vo potential and the VL potential after exposure to light at 7.5 lux for seconds were measured. The results are shown in Table 7.
表 7
上表に示す様に、シリコーンオイルを添加した試料の3
000枚耐久後のVL変動は非常に大きい。それに対し
、本発明品においては耐久変動は小さい。Table 7 As shown in the table above, 3 samples added with silicone oil
The VL fluctuation after running for 000 sheets is very large. On the other hand, in the product of the present invention, the durability fluctuation is small.
実施例8
下記構造式のジスアゾ顔料3部、及び
実施例1で用いたマレインイミド系樹脂10部モノクロ
ルベンゼン50部を1φガラスピーズを用いたサンドミ
ル装置で20時間分散した。この液にiJ料11haの
シリコーン系クシ型グラフトポリマーを固形分として0
,2部、実施例1で示した構造式のヒドラゾン化合物1
0部を加え溶解した。この分散溶液を実施例1と同様に
して作成した下引き層を有する基体上に浸漬塗布し、1
00℃1時間乾燥して19μの光導電層を形成した。こ
れを試料27とする。Example 8 3 parts of a disazo pigment having the following structural formula, 10 parts of the maleimide resin used in Example 1, and 50 parts of monochlorobenzene were dispersed for 20 hours in a sand mill apparatus using 1φ glass beads. Add 11 ha of iJ material to this liquid as a solid content of silicone comb-shaped graft polymer.
, 2 parts, hydrazone compound 1 having the structural formula shown in Example 1
0 parts was added and dissolved. This dispersion solution was applied by dip coating onto a substrate having an undercoat layer prepared in the same manner as in Example 1.
The photoconductive layer was dried at 00° C. for 1 hour to form a 19 μm photoconductive layer. This is designated as sample 27.
比較のためシリコーン系クシ型グラフトポリマーを添加
しないものを上記と同様にして作成した。For comparison, a sample without the silicone comb-shaped graft polymer was prepared in the same manner as above.
これを試料28とする。This is designated as sample 28.
これらの試料を実施例1と同一の条件下で耐久性評価を
行なった。その結果を表8に示す。The durability of these samples was evaluated under the same conditions as in Example 1. The results are shown in Table 8.
表 8
比較例
シリコーン系クシ型グラフトポリマーの代わりにシリコ
ーンオイル(商品名KF96信越シ信越シリコーン金製
形分として1.0部を用いたほかは実施例8と同様に作
成した試料を試料29とする。Table 8 Comparative Examples A sample prepared in the same manner as Example 8 was used as Sample 29, except that 1.0 part of silicone oil (trade name: KF96 Shin-Etsu Silicone was used as the molding component) in place of the silicone-based comb-shaped graft polymer. do.
この試料を実施例1及び3と同様の条件下で耐久性評価
を行なったが、地力ブリがはなはだしく、更にくり返し
コピーによってカブリの度合が大きくなった。また試料
29を作成して1か月後に観察するとシリコーンオイル
が表面層に移行し、しみ状に浮き出ていた。一方、シリ
コーン系クシ型グラフトポリマーを添加した試料におい
てはこの様な経時変化は認められず、初期と同様の観察
、特性を示した。Durability evaluation of this sample was conducted under the same conditions as in Examples 1 and 3, but there was considerable blurring, and the degree of fogging increased due to repeated copying. Further, when Sample 29 was observed one month after its preparation, it was found that the silicone oil had migrated to the surface layer and stood out in the form of a stain. On the other hand, in the sample to which the silicone-based comb-shaped graft polymer was added, no such change over time was observed, and the same observation and characteristics as in the initial stage were observed.
実施例9
次に前記試料1〜30についてウレタンゴムブレードと
表面層との間の摩擦力及び試料Na15〜20.25〜
29に関してA4紙の実焼耐久1000枚での表面層の
削れ量を測定した。その結果を表9に示す。Example 9 Next, regarding the samples 1 to 30, the frictional force between the urethane rubber blade and the surface layer and the sample Na15 to 20.25 to
Regarding No. 29, the amount of abrasion of the surface layer was measured after 1000 sheets of A4 paper were actually burned. The results are shown in Table 9.
表 9
*2 削れ量:初期における表面層膜厚−耐久後表面層
膜厚上表に示す様にシリコーン系クシ型グラフトポリマ
ーを添加した本発明品並びに、シリコーンオイルを添加
した比較試料は無添加試料に比較し、著しく摩擦抵抗が
低い。Table 9 *2 Amount of abrasion: Initial surface layer film thickness - Surface layer film thickness after durability As shown in the table above, the product of the present invention to which silicone-based comb-shaped graft polymer was added and the comparative sample to which silicone oil was added had no additive. Frictional resistance is significantly lower than that of the sample.
しかしながら削れ量に関しては、本発明におけるシリコ
ーン系クシ型ポリマーを添加したサンプルが最も小さい
値、即ち削れにくい事を示している。However, regarding the amount of abrasion, the sample to which the silicone-based comb-shaped polymer of the present invention was added has the smallest value, ie, shows that it is difficult to abrade.
さらにシリコーンオイル添加系においては前記の様に放
置安定性や耐久時の電位安定性に劣る。Furthermore, as mentioned above, silicone oil-added systems are inferior in storage stability and potential stability during durability.
以上から明らかな如く本発明の電子写真感光体は特定の
シリコーン系クシ型グラフトポリマーをマレインイミド
系樹脂に配合することにより、表面の潤滑性に優れ、す
べり抵抗が低く結果的に耐摩耗性に優れ、感光体に耐久
性を付与する。また、すべり抵抗が低く、トナー融着等
のクリーニング不良がなく、常に高品位の画像を得るこ
とができる。As is clear from the above, the electrophotographic photoreceptor of the present invention has excellent surface lubricity, low slip resistance, and wear resistance by blending a specific silicone-based comb-shaped graft polymer with maleimide-based resin. Excellent and imparts durability to the photoreceptor. In addition, the slip resistance is low, there are no cleaning defects such as toner fusion, and high-quality images can always be obtained.
Claims (7)
換基を有してもよいアルキル基またはアリール基を示し
、nは平均重合度を示す。) 及び/又は一般式(II) ▲数式、化学式、表等があります▼(II) (式中、R_6、R_7は置換基を有してもよいアルキ
ル基またはアリール基を示し、nは平均重合度を示す。 ) で示されるシリコーンと少なくとも一般式(III)▲数
式、化学式、表等があります▼(III) (式中、R_8、R_9、R_1_0は水素原子、ハロ
ゲン原子、置換基を有してもよいアルキル基またはアリ
ール基を示し、R_1_1は置換基を有してもよいアル
キル基またはアリール基を示し、Xはハロゲン原子、置
換基を有してもよいアルコキシ基を示し、mは1〜3の
整数を示す。) で示される化合物との縮合反応生成物と重合性不飽和結
合含有化合物との共重合体であるシリコーン系クシ型グ
ラフトポリマーとマレインイミド系樹脂を、少なくとも
基体より最も離隔せる層中に含有せることを特徴とする
電子写真感光体。(1) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R_1, R_2, R_3, R_4, R_5 represent an alkyl group or an aryl group that may have a substituent. , n indicates the average degree of polymerization) and/or general formula (II) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (II) (In the formula, R_6 and R_7 are alkyl groups that may have substituents or represents an aryl group, and n represents the average degree of polymerization) and at least the general formula (III) ▲ Numerical formula, chemical formula, table, etc. ▼ (III) (In the formula, R_8, R_9, R_1_0 are hydrogen atoms , represents a halogen atom, an alkyl group or an aryl group that may have a substituent, R_1_1 represents an alkyl group or an aryl group that may have a substituent, and X represents a halogen atom, an alkyl group that may have a substituent, or an aryl group that may have a substituent. a silicone-based comb-shaped graft polymer which is a copolymer of a condensation reaction product with a compound represented by (m is an integer of 1 to 3) and a polymerizable unsaturated bond-containing compound, and malein. An electrophotographic photoreceptor characterized in that an imide resin is contained at least in a layer furthest from a substrate.
、基体より最も離隔する層が前記非感光性の表面層であ
る特許請求の範囲第(1)項記載の電子写真感光体。(2) The electrophotographic photosensitive material according to claim (1), which has a photosensitive layer and a non-photosensitive surface layer as constituent components, and the layer that is furthest away from the substrate is the non-photosensitive surface layer. body.
を有する特許請求の範囲第(2)項記載の電子写真感光
体。(3) The electrophotographic photoreceptor according to claim (2), wherein the photosensitive layer has a laminated structure of a charge generation layer and a charge transport layer.
許請求の範囲第(1)項記載の電子写真感光体。(4) The electrophotographic photoreceptor according to claim (1), which has a photosensitive layer as the layer furthest from the substrate.
光層を構成分として有し、基体より最も離隔する層が前
記電荷輸送層である特許請求の範囲第(1)項記載の電
子写真感光体。(5) The electronic device according to claim (1), which has a photosensitive layer having a laminated structure of a charge generation layer and a charge transport layer as a component, and the charge transport layer is the layer furthest away from the substrate. Photographic photoreceptor.
光層を構成分として有し、基体より最も離隔する層が前
記電荷発生層である特許請求の範囲第(1)項記載の電
子写真感光体。(6) The electronic device according to claim (1), which has a photosensitive layer having a laminated structure of a charge generation layer and a charge transport layer as a component, and the charge generation layer is the layer furthest away from the substrate. Photographic photoreceptor.
シ型グラフトポリマーの含量が0.01〜10重量%の
範囲内である特許請求の範囲第(1)項乃至第(6)項
のうちの1に記載の電子写真感光体。(7) One of claims (1) to (6), wherein the content of the silicone comb-shaped graft polymer in the layer furthest from the substrate is within the range of 0.01 to 10% by weight. The electrophotographic photoreceptor described in .
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5067886A JPS62208055A (en) | 1986-03-10 | 1986-03-10 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5067886A JPS62208055A (en) | 1986-03-10 | 1986-03-10 | Electrophotographic sensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS62208055A true JPS62208055A (en) | 1987-09-12 |
Family
ID=12865591
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP5067886A Pending JPS62208055A (en) | 1986-03-10 | 1986-03-10 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62208055A (en) |
-
1986
- 1986-03-10 JP JP5067886A patent/JPS62208055A/en active Pending
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