JPH022576A - Photoconductive toner - Google Patents
Photoconductive tonerInfo
- Publication number
- JPH022576A JPH022576A JP63146235A JP14623588A JPH022576A JP H022576 A JPH022576 A JP H022576A JP 63146235 A JP63146235 A JP 63146235A JP 14623588 A JP14623588 A JP 14623588A JP H022576 A JPH022576 A JP H022576A
- Authority
- JP
- Japan
- Prior art keywords
- toner
- photoconductive
- formula
- group
- obtd
- 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
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229920000620 organic polymer Polymers 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229920002382 photo conductive polymer Polymers 0.000 abstract description 17
- 239000002245 particle Substances 0.000 abstract description 15
- 239000000463 material Substances 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 239000000654 additive Substances 0.000 abstract description 6
- 239000000049 pigment Substances 0.000 abstract description 5
- 239000006185 dispersion Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 239000000178 monomer Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- -1 etc. Chemical compound 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000036211 photosensitivity Effects 0.000 description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 2
- 229910000859 α-Fe Inorganic materials 0.000 description 2
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
- XHAFIUUYXQFJEW-UHFFFAOYSA-N 1-chloroethenylbenzene Chemical compound ClC(=C)C1=CC=CC=C1 XHAFIUUYXQFJEW-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-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
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- XUYDVDHTTIQNMB-UHFFFAOYSA-N 3-(diethylamino)propyl prop-2-enoate Chemical compound CCN(CC)CCCOC(=O)C=C XUYDVDHTTIQNMB-UHFFFAOYSA-N 0.000 description 1
- OTKLRHWBZHQJOP-UHFFFAOYSA-N 3-aminopropyl prop-2-enoate Chemical compound NCCCOC(=O)C=C OTKLRHWBZHQJOP-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- IYHIFXGFKVJNBB-UHFFFAOYSA-N 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonic acid Chemical compound C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S(O)(=O)=O IYHIFXGFKVJNBB-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- LTGPFZWZZNUIIK-LURJTMIESA-N Lysol Chemical compound NCCCC[C@H](N)CO LTGPFZWZZNUIIK-LURJTMIESA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 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
- 239000003708 ampul Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- HBHZKFOUIUMKHV-UHFFFAOYSA-N chembl1982121 Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HBHZKFOUIUMKHV-UHFFFAOYSA-N 0.000 description 1
- PZTQVMXMKVTIRC-UHFFFAOYSA-L chembl2028348 Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 PZTQVMXMKVTIRC-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PLYDMIIYRWUYBP-UHFFFAOYSA-N ethyl 4-[[2-chloro-4-[3-chloro-4-[(3-ethoxycarbonyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)diazenyl]phenyl]phenyl]diazenyl]-5-oxo-1-phenyl-4h-pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC=CC=2)C(=O)C1N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(=N1)C(=O)OCC)C(=O)N1C1=CC=CC=C1 PLYDMIIYRWUYBP-UHFFFAOYSA-N 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000006233 lamp black Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
- 235000010187 litholrubine BK Nutrition 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 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
- 230000001443 photoexcitation Effects 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- RBKBGHZMNFTKRE-UHFFFAOYSA-K trisodium 2-[(2-oxido-3-sulfo-6-sulfonatonaphthalen-1-yl)diazenyl]benzoate Chemical compound C1=CC=C(C(=C1)C(=O)[O-])N=NC2=C3C=CC(=CC3=CC(=C2[O-])S(=O)(=O)O)S(=O)(=O)[O-].[Na+].[Na+].[Na+] RBKBGHZMNFTKRE-UHFFFAOYSA-K 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/09—Colouring agents for toner particles
- G03G9/0926—Colouring agents for toner particles characterised by physical or chemical properties
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、光導電性トナーに関し、より詳細には粒子個
々の感光特性及び着色性が均質な光導電性トナーに関す
る。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a photoconductive toner, and more particularly to a photoconductive toner in which each particle has uniform photosensitive characteristics and colorability.
（従来技術）
電子写真技術を応用した画像形成方法の代表的なものと
しては、感光体上に形成した静電潜像をトナーにより顕
像化してトナー画像を形成し、このトナー画像を普通紙
等の転写材料に転写して複写物を得るゼログラフィー法
、感光材料を直接現像して複写物とするエレクトロフッ
クス法などがあげられるが、これらの方法はいずれも現
像工程を必要とするため、その実施での装置が複雑かつ
高価になるという欠点がある。(Prior art) A typical image forming method applying electrophotographic technology is to visualize an electrostatic latent image formed on a photoreceptor with toner to form a toner image, and then print this toner image on plain paper. Examples include the xerography method, which obtains a copy by transferring the photosensitive material to a transfer material, and the electrofox method, which produces a copy by directly developing the photosensitive material, but all of these methods require a development step. The disadvantage is that the equipment for its implementation is complex and expensive.
そこでかかる欠点を解消するものとして、光導電性トナ
ーを導電性基板上に均一に付着させ、トナー層を形成し
、このトナー層に帯電及び像露光を施し、露光部の光導
電性トナーの電荷を消失するか或いは弱化して静電潜像
を形成した後、未露光部の電荷を有する光２４電性トナ
ーのみを転写材料に転写するようにした画像形成方法が
知られている。この画像形成方法に使用される光導電性
トナーは一般に、結着樹脂中に着色剤と共に光導電性物
質を分散させた樹脂微粒子であり、光導電性物質として
は、酸化亜鉛、セレン等の無機系の光４電体やポリビニ
ルカルバゾール（ＰＶＣ２）、ヒドラゾン等の光導電性
高分子や低分子光導電性化合物の有機系の光導電体が使
用されている。そして、これらの光導電体は可視光に対
する光導電性が乏しいために、実用に際しては可視光で
の感光性と増感性をしめず有機色素や顔料等の増感剤を
光導電体と共に使用している。このように光導電性トナ
ーは色相と光導電性及び感光性など多くの機能を担った
樹脂微粒子であり、良好な現像特性をしめすには、各添
加剤を結着樹脂中に一様に分散し、トナー表面に存在さ
せ各トナー粒子表面の特性を均一にする必要がある。To solve this problem, a photoconductive toner is uniformly deposited on a conductive substrate to form a toner layer, and this toner layer is charged and imagewise exposed to charge the photoconductive toner in the exposed area. An image forming method is known in which, after forming an electrostatic latent image by eliminating or weakening the electrostatic latent image, only the photoconductive toner having an electric charge in the unexposed area is transferred to a transfer material. The photoconductive toner used in this image forming method is generally resin fine particles in which a photoconductive substance is dispersed together with a coloring agent in a binder resin. Organic photoconductors such as phototetraconductors, photoconductive polymers such as polyvinyl carbazole (PVC2), and hydrazone, and low-molecular photoconductive compounds are used. Since these photoconductors have poor photoconductivity to visible light, in practical use, sensitizers such as organic dyes and pigments are used together with the photoconductors without reducing photosensitivity and sensitization to visible light. ing. In this way, photoconductive toner is resin fine particles that have many functions such as hue, photoconductivity, and photosensitivity, and in order to exhibit good development characteristics, each additive must be uniformly dispersed in the binder resin. However, it is necessary to make the characteristics of the surface of each toner particle uniform by making it exist on the toner surface.
（発明が解決しようとする問題点）
しかしながら、着色剤と光導電体及び増感剤としての顔
料など各成分をトナー粒子個々の結着樹脂中に微細且つ
一様に分散し、粒子表面に存在させることは困難であり
、特に増感剤としての顔料は結着樹脂中で凝集体として
存在しやすく、局所的に分散不良を起こすためにトナー
粒子個々の現像特性を一定にすることは困難であった。(Problems to be Solved by the Invention) However, each component such as a colorant, a photoconductor, and a pigment as a sensitizer is finely and uniformly dispersed in the binder resin of each toner particle, and is present on the particle surface. In particular, pigments used as sensitizers tend to exist as aggregates in the binder resin, which causes localized poor dispersion, making it difficult to make the development characteristics of individual toner particles constant. there were.
また、光導電性カラートナーの場合、光導電体と増感剤
がトナーの色相を粗悪なものにし、鮮彩さを欠く画像に
なってしまうという欠点もあった。In the case of photoconductive color toners, the photoconductor and sensitizer also have the disadvantage that the toner has a poor hue, resulting in images that lack vividness.
本発明者は鋭意研究の結果高分子内で電荷を生成すると
ともに、生成した電荷が同一高分子内の電荷輸送部位を
通じて移動することを特徴とする光導電性重合体を先に
提案した。As a result of extensive research, the present inventors have previously proposed a photoconductive polymer that is characterized in that it generates charges within the polymer and that the generated charges move through charge transport sites within the same polymer.
そこで、本発明の目的は先に提案した光導電性重合体を
構成成分とすることで、増感剤としてキャリア発生顔料
を含有することなく可視光で光導電性を示す光導電性ト
ナーを提供するにある。Therefore, an object of the present invention is to provide a photoconductive toner that exhibits photoconductivity in visible light without containing a carrier-generating pigment as a sensitizer by using the previously proposed photoconductive polymer as a constituent component. There is something to do.
本発明の他の目的は、できるだけ少ない構成成分からな
り、粒子個々の感光特性が均一な光導電性トナーを提供
するにある。Another object of the present invention is to provide a photoconductive toner comprising as few components as possible and having uniform photosensitive characteristics of each particle.
更に、本発明の他の目的は、色相の鮮彩な光導電性カラ
ートナーを提供するにある。Still another object of the present invention is to provide a photoconductive color toner with a vivid hue.
（問題点を解決するための手段）
本発明の光導電性重合体は、有機高分子光導電体の主鎖
および／あるいは側鎖に、下記構造式のローダニン誘導
体
式中Ｒ１は下記一般式
で表される基であり、Ｒ３、Ｒ２は同一または異なって
、水素原子、アルキル基、置換または未置換のアリール
基を示し、Ｒ３は炭素数１〜６の低級アルキル基、水酸
基を示し、Ｒ４は水素原子、炭素数１〜６の低級アルキ
ル基、置換または未置換のアリール基、水酸基を示す、
を具備した光導電性重合体成分を含有することを特徴と
する光導電性トナーが提供される。(Means for Solving the Problems) The photoconductive polymer of the present invention has a rhodanine derivative of the following structural formula in the main chain and/or side chain of an organic polymer photoconductor, where R1 is the following general formula. R3 and R2 are the same or different and represent a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, R3 represents a lower alkyl group having 1 to 6 carbon atoms or a hydroxyl group, and R4 represents a Provided is a photoconductive toner comprising a photoconductive polymer component representing a hydrogen atom, a lower alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group, or a hydroxyl group. .
（作用）
本発明の光導電性１−ナーは、有機高分子光導電体の主
鎖および／あるいは側鎖に、下記構造式で表されるロー
ダニン誘導体を具備した光導電性重合体成分を含有して
おり、上記構造式中ローダニン環部が電子受容体、ロー
ダニン環の５位に有するＲは下記一般式
酸基を示す）で表される基であり電子供与体と考えられ
るため、可視光の吸収はこの電子受容体と電子供与体か
らなる分子内電荷移動型錯体の形成による。(Function) The photoconductive 1-ner of the present invention contains a photoconductive polymer component having a rhodanine derivative represented by the following structural formula in the main chain and/or side chain of an organic polymer photoconductor. In the above structural formula, the rhodanine ring part is an electron acceptor, and R at the 5th position of the rhodanine ring is a group represented by the following general formula (representing an acid group), and is considered to be an electron donor. The absorption of is due to the formation of an intramolecular charge transfer complex consisting of this electron acceptor and electron donor.
つまり、基底状態の電子供与体に非掻在化していたπ電
子が電子受容体の空軌道に遷移する際に光エネルギーを
吸収して発色する。光キャリアは、この光励起により発
生するのである。That is, when the π electrons, which were not intercalated in the electron donor in the ground state, are transferred to the empty orbit of the electron acceptor, they absorb light energy and develop color. Photocarriers are generated by this photoexcitation.
従って、先に提案した光導電性重合体成分は例えば式中
Ｒが下記一般式
（式中Ｒ，，Ｒ２は同一または異なって、水素原子、ア
ルキル基、置換または未置換のアリール基を示し、Ｒ３
は炭素数１〜６の低級アルキル基、水酸基を示し、Ｒ４
は水素原子、炭素数１〜６の低級アルキル基、置換また
は未置換のアリール基、水（式中Ｒ１，ＲＺは特許請求
の範囲第１項と同義である）で表される基の場合は橙色
、
および
（式中Ｒ３は特許請求の範囲第１項と同義である）で表
される基の場合は黄色、
（式中Ｒ４は特許請求の範囲第１項と同義である）で表
される基の場合は赤色、
本発明の光導電性トナーの原料化合物である光導電性重
合体の適当な例は、これに限定されるものではないが次
の通りである。Therefore, the photoconductive polymer component proposed above can be used, for example, in the formula where R is the following general formula (wherein R, , R2 are the same or different and represent a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, R3
represents a lower alkyl group having 1 to 6 carbon atoms or a hydroxyl group, and R4
In the case of a group represented by a hydrogen atom, a lower alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group, or water (in the formula, R1 and RZ are as defined in claim 1), orange, and yellow in the case of a group represented by (in the formula, R3 has the same meaning as in claim 1); Suitable examples of the photoconductive polymer that is a raw material compound for the photoconductive toner of the present invention include, but are not limited to, the following.
（式中Ｒ４は特許請求の範囲第１項と同義である）で表
される基の場合は青色を呈し、それ自身が鮮やかな色を
持つのである。さらに先に提案した光導電性成分は、有
機高分子光導電体をも有しているためホール輸送機能を
持ち、ローダニン色素で発生した光キャリアを同一高分
子内のホール輸送部位を通して移動可能なポリマー型の
光導電性材料である。In the case of the group represented by the formula (in which R4 has the same meaning as in claim 1), it exhibits a blue color and itself has a bright color. Furthermore, the photoconductive component proposed earlier has a hole transport function because it also has an organic polymer photoconductor, and is capable of transporting photocarriers generated by the rhodanine dye through the hole transport site within the same polymer. It is a polymer type photoconductive material.
従って、定着樹脂中に先に提案した光導電性重合体成分
を相溶してトナー化するだけで、粒子個々の感光特性が
均一である本発明の光導電性トナーが得られる。Therefore, the photoconductive toner of the present invention, in which each particle has uniform photosensitive properties, can be obtained simply by dissolving the previously proposed photoconductive polymer component in the fixing resin to form a toner.
（発明の好適対応） ｌｈ （以下余白） Ｃ１１゜ ｌｌｚ ＋０１１□ Ｃｌｌ ｈ「−代Ｈｚ−Ｃ ＋Ｖ −ＧＣＨ，−Ｃ）Ｉ）−７ 一＋ＣＩｈ−Ｃ１１）−７ Ｃ＝０ Ｃ＝０ ＣＢ。(Preferred response to the invention) lh (Margin below) C11゜ llz +011□ Cll h”-Temporary Hz-C +V -GCH, -C)I)-7 1+CIh-C11)-7 C=0 C=0 C.B.
Ｃ１１□ Ｈ２ Ｃ１！２ −ＧＣＩＩ□−Ｃ１１）−。C11□ H2 C1!2 -GCII□-C11)-.
Ｃ＝Ｑ ＣＩ＋□ Ｃ１１□ ＣＩ＋□ 一４Ｃ１１，−Ｃ）Ｉ）−。C=Q CI+□ C11□ CI+□ -4C11,-C)I)-.
Ｃ１！２ ＣＩ＋！ ＪＣＩＩ ｚ −ＣＩｔ ）−。C1!2 CI+! JCII z-CIt)-.
Ｃ，０ ＣＩ＋□ ＣＩ＋□ Ｃ２＋Ｉ Ｓ Ｃ２Ｈ。C,0 CI+□ CI+□ C2+I S C2H.
ＵＬ、１１３すしＩ＋１
Ｃ１１３
Ｃ１１゜
上記重合体をブレンドする定着用の樹脂媒質としては、
この種のトナーの製法に使用される樹脂類が使用され、
特に好適なものとしては、種々のモノ乃至はジエチレン
系の不飽和単量体、特に（ａ）ビニル芳香族単量体、（
ｂ）アクリル系単量体の単独重合体や共重合体等が使用
される。UL, 113 Sushi I+1 C113 C11゜The fixing resin medium for blending the above polymers is as follows:
The resins used in the manufacturing method of this type of toner are used,
Particularly preferred are various mono- or diethylenically unsaturated monomers, especially (a) vinyl aromatic monomers, (
b) Homopolymers and copolymers of acrylic monomers are used.
上記（ａ）の単量体としは、スチレン、ビニルトルエン
、α−メチルスチレン、α−クロルスチレン、ビニルキ
シレン、等やビニルナフタレン等をあげることができ、
（ｂ）の単量体としてはメタクリル酸、エチルアクリレ
ート、メチルメタクレート、ブチルアクリレート、ブチ
ルメタクリレート、２−エチルへキシルアクリレート、
２−エチルへキシルメタクリレート、３−ヒドロキシプ
ロピルアクリレート、２−ヒドロキシエチルメタクリレ
ート、３−アミノプロピルアクリレート、３−Ｎ、Ｎ−
ジエチルアミノプロピルアクリレート、アクリルアミド
等を挙げることができる。Examples of the monomer (a) above include styrene, vinyltoluene, α-methylstyrene, α-chlorostyrene, vinylxylene, vinylnaphthalene, etc.
Monomers (b) include methacrylic acid, ethyl acrylate, methyl methacrylate, butyl acrylate, butyl methacrylate, 2-ethylhexyl acrylate,
2-ethylhexyl methacrylate, 3-hydroxypropyl acrylate, 2-hydroxyethyl methacrylate, 3-aminopropyl acrylate, 3-N,N-
Examples include diethylaminopropyl acrylate and acrylamide.
これらの単量体（ａ）あるいは（ｂ）と組合せて、或い
は単独で使用される他の単量体としては、ブタジェン、
イソプレン、クロロプレン等の他には無水マレイン酸、
フマル酸、クロトン酸、イタコン酸等の他のエチレン系
不飽和カルボン酸或いはそのエステル類や、酢酸ビニル
等のびにるエステル類、ビニルピリジン、ビニルピロリ
ドン、ビニルエーテル類、アクリロニトリル、塩化ビニ
ル、塩化ビニリデン等を挙げることができる。これらの
樹脂の分子量は３，０００乃至３００，０００゜特に５
，０００乃至２００，０００の範囲にあるのが望ましい
。Other monomers used in combination with these monomers (a) or (b) or alone include butadiene,
In addition to isoprene, chloroprene, etc., maleic anhydride,
Other ethylenically unsaturated carboxylic acids or their esters such as fumaric acid, crotonic acid, itaconic acid, vinyl esters such as vinyl acetate, vinylpyridine, vinylpyrrolidone, vinyl ethers, acrylonitrile, vinyl chloride, vinylidene chloride, etc. can be mentioned. The molecular weight of these resins is 3,000 to 300,000°, especially 5
,000 to 200,000.
そして、先に提案した光導電性重合体を上記定着樹脂媒
質当り５０乃至２００重世部使用することで、感光性と
光導電性及び定着性の良好な本発明の光導電性トナーと
なる。By using 50 to 200 parts of the previously proposed photoconductive polymer per fixing resin medium, the photoconductive toner of the present invention has good photosensitivity, photoconductivity, and fixability.
また、先に提案した光導電性重合体を製造するにあたっ
て例えば、上述した定着樹脂媒質となる単量体に反応性
置換基を導入しローダニン誘導体を反応させて得られた
単量体と、有機高分子光導電体を構成する単量体とを共
重合させて、直接定着樹脂媒質を含有させることもでき
る。In addition, in producing the photoconductive polymer proposed earlier, for example, a monomer obtained by introducing a reactive substituent into the monomer that will serve as the fixing resin medium and reacting it with a rhodanine derivative, and an organic A direct fixing resin medium can also be included by copolymerizing the monomers that make up the polymeric photoconductor.
また、トナーが熱定着性トナーであるとき、上記重合体
の軟化点は５０〜２００°Ｃ１好ましくは、軟化点７０
〜１７０°Ｃを有するものが好ましい。Further, when the toner is a heat fixable toner, the softening point of the polymer is 50 to 200° C. Preferably, the softening point is 70° C.
~170°C is preferred.
また、光導電性トナーを黒色乃至他の色相に着色する着
色剤としては、例えばカーボンブラック、ランプブラッ
ク（Ｃ，Ｉ、Ｎｏ、７７２６６） 、クロムイエロー（
Ｃ，１，Ｎｏ、１４０９０）、ハンザイエロー（Ｃ，１
，Ｎｏ、 １１６６０．１１６８０ 、等）、ベンジジ
ンイエロー（Ｃ，１，Ｎｏ。In addition, examples of colorants that color the photoconductive toner black or other hues include carbon black, lamp black (C, I, No., 77266), chrome yellow (
C, 1, No. 14090), Hansa Yellow (C, 1
, No. 11660.11680, etc.), benzidine yellow (C, 1, No.
２１１００等）、スレンイエローＧ（Ｃ，１，Ｎｏ、７
０６００）、キノリンイエロー（Ｃ０１，Ｎｏ、４７０
０５）、パーマネントオレンジＧＴＲ（Ｃ，１，Ｎｏ、
１２３０５） 、プラシンオレンジ（Ｃ，１，Ｎｏ、２
１１６０）、ウォッチヤングレッド（Ｃ，１，Ｎｏ。21100 etc.), Suren Yellow G (C, 1, No. 7)
0600), Quinoline Yellow (C01, No. 470)
05), Permanent Orange GTR (C, 1, No.
12305), plasticine orange (C, 1, No, 2
1160), Watch Young Red (C, 1, No.
１５８６８）、パーマネントレッド（Ｃ，１，Ｎｏ、１
２３１０等）、ブリリアントカーミン３Ｂ（Ｃ，１，Ｎ
ｏ、１６１０５）、ブリリアントカーミン６Ｂ （Ｃ，
１，Ｎｏ、 １５８５０）、デュポンオイルレッド（Ｃ
，１，Ｎｏ、２６１０５）、ピラゾロンレッド（Ｃ。15868), permanent red (C, 1, No, 1
2310 etc.), brilliant carmine 3B (C, 1, N
o, 16105), brilliant carmine 6B (C,
1, No. 15850), DuPont Oil Red (C
, 1, No. 26105), Pyrazolone Red (C.
１、Ｎｏ、２１１２０）、リソールレッド（Ｃ，ｌＮｏ
、１５６３０）、ローダミンＢ レーキ（Ｃ，ｌＮｏ、
４５１７０）、レーキ−レッドＣ（Ｃ，１，Ｎｏ、４５
４３５） 、アニリンブルー（Ｃ，１，Ｎｏ。1, No. 21120), Lysol Red (C, lNo.
, 15630), Rhodamine B Lake (C,lNo,
45170), Lake Red C (C, 1, No. 45
435), Aniline Blue (C, 1, No.
７７１０３）、カルコオイルブルー（Ｃ，１，Ｎｏ、ａ
ｚｏｅｃ Ｂｌｕｅ３）、メチレンブルークロライド（
Ｃ，１，Ｎｏ、５２０１５）、フタロシアニンブルー（
Ｃ，１，Ｎｏ、７４２６０）、マラカイドグリーンオク
サレート（Ｃ，１，Ｎｏ、４２０００）等、またはニグ
ロシン染料、スピロンブラック等やＣ，１，Ｓ。77103), Calco Oil Blue (C, 1, No, a
zoec Blue3), methylene blue chloride (
C, 1, No. 52015), Phthalocyanine Blue (
C,1, No. 74260), malachide green oxalate (C,1, No. 42000), etc., or nigrosine dye, Spiron black, etc., C,1,S.
Ｉｖｅｎｔ Ｙｅｌｌｏｗ ６０ 、Ｃ，１，５ｏｌｖ
ｅｎｔ Ｒｅｄ ２７、Ｃ，１，Ｓ。Event Yellow 60, C, 1,5olv
ent Red 27, C, 1, S.
１ｖｅｎｔ Ｂｌｕｅ ３５ 、Ｃ，１Ｓｏｌｖｅｎｔ
Ｇｒｅｅｎ １５、Ｃ，１，Ｓ。1vent Blue 35, C, 1Solvent
Green 15, C, 1, S.
１ｖｅｎｔ Ｉｌｒｏｗｎ ５ 、等の油溶性染料など
が例示され、特に光導電性と着色性の点から油溶性染料
が好ましい。Examples include oil-soluble dyes such as 1vent Ilrown 5, and oil-soluble dyes are particularly preferred from the viewpoint of photoconductivity and colorability.
これらの着色剤は、一種または二種以上混合して用いら
れ、例えば結着樹脂１００重量部当りｌ乃至３０重量部
好ましくは２乃至２０重量部用いられる。These colorants may be used singly or in combination of two or more, for example, 1 to 30 parts by weight, preferably 2 to 20 parts by weight, per 100 parts by weight of the binder resin.
なお、必要に応じてトナーの電荷を制御するため、上記
トナーは、他の添加剤として、電荷制御剤、例えば、ニ
グロシン染料（Ｃ，１，Ｎｏ、５０４１５Ｂ） 、オイ
ルブラック（Ｃ０１，Ｎｏ、２６１５０）、スピロンブ
ラック等の油溶性染料や、ナフテン酸、サリチル酸、オ
クチル酸、後記脂肪酸、樹脂酸のマンガン、鉄、コバル
ト、鉛、亜鉛、セリウム、カルシウム、ニッケル等の金
属塩である金属石鹸等あるいは含金属アゾ染料、ピリミ
ジン化合物、アルキルサリチル酸金属キレート等を、前
記結着樹脂当り０．０１〜５重量％含有させてもよい。In addition, in order to control the charge of the toner as necessary, the above toner may contain a charge control agent such as nigrosine dye (C, 1, No. 50415B), oil black (C01, No. 26150) as other additives. ), oil-soluble dyes such as Spiron black, naphthenic acid, salicylic acid, octylic acid, fatty acids mentioned below, resin acids such as manganese, iron, cobalt, lead, zinc, cerium, calcium, metal soaps that are metal salts of nickel, etc. Alternatively, metal-containing azo dyes, pyrimidine compounds, alkyl salicylic acid metal chelates, etc. may be contained in an amount of 0.01 to 5% by weight based on the binder resin.
また、上記トナーは、前記定着ローラにトナーが付着す
るのを防止するため、オフセット防止剤、例えば、低分
子量ポリプロピレン、低分科量ポリエチレン、パラフィ
ンワックスなどの各種ワックス、炭素原子数４以上のオ
レフィン単量体の低分子量オレフィン重合体、脂肪酸ア
ミド、シリコーンオイル等を、トナー当り０．５〜１５
重量％含有してもよい。In addition, in order to prevent the toner from adhering to the fixing roller, the toner may contain an anti-offset agent, such as various waxes such as low molecular weight polypropylene, low molecular weight polyethylene, and paraffin wax, and olefin monomers having 4 or more carbon atoms. 0.5 to 15% of low molecular weight olefin polymer, fatty acid amide, silicone oil, etc. per toner.
It may be contained in a weight percent.
なお、必要に応じてトナーの流動性等を改良するため、
シランカップリング剤、シリコーンやフッ素化合物等の
外添剤によりトナーを表面処理を行ってもよい。In addition, in order to improve the fluidity of the toner as necessary,
The toner may be surface-treated with an external additive such as a silane coupling agent, silicone, or a fluorine compound.
また、本発明の光導電性トナーの製造方法は、有機高分
子光導電体の主鎖および／あるいは側鎖にローダニン誘
導体を具備した光導電性重合体及び必要に応じて着色剤
やその他の添加剤を混合し、混練した後これを微粉砕す
る。あるいは、前記混合物を適当な溶媒に混合分散して
、得られる溶液をスプレードライ法によって粒径５乃至
５０μｍのトナーが生成される。In addition, the method for producing the photoconductive toner of the present invention includes a photoconductive polymer having a rhodanine derivative in the main chain and/or side chain of an organic polymer photoconductor, and a colorant or other additives as necessary. After mixing and kneading the ingredients, the mixture is pulverized. Alternatively, a toner having a particle size of 5 to 50 μm is produced by mixing and dispersing the mixture in a suitable solvent and spray-drying the resulting solution.
本発明のトナーを使用する画像形成としては、アルミ板
、ブリキ板等の金属板やこれらのドラムの他に、ネサガ
ラス等の透明導電性基体が使用される。基体上にトナー
相を形成するには、それ自体公知の任意の手段を用いる
ことができ、例えば前述したトナー組成物を磁性キャリ
アと混合して、この二成分系組成物を形成し、これを内
部に磁石を備えたスリーブ上に供給して時期ブラシを形
成し、この磁気ブラシでと導電性基体を摺擦し、基体上
にトナー層を形成させる。また、帯電トナーをファブラ
シ上に支持し、これで導電性基体を摺擦することにより
、基体上にトナー層を形成させる。この場合、導電性基
体とスリーブ或いはファーブラシとの間にバイアス電圧
を印加すると、トナー層の形成が一層容易に行われる。For image formation using the toner of the present invention, in addition to metal plates such as aluminum plates and tin plates and drums thereof, transparent conductive substrates such as Nesa glass are used. Any means known per se can be used to form the toner phase on the substrate, for example by mixing the toner composition described above with a magnetic carrier to form a two-component composition, which The magnetic brush is supplied onto a sleeve having a magnet therein, and the magnetic brush rubs against the conductive substrate to form a toner layer on the substrate. Further, the charged toner is supported on a fabrush and rubbed against the conductive substrate with this, thereby forming a toner layer on the substrate. In this case, if a bias voltage is applied between the conductive substrate and the sleeve or fur brush, the toner layer can be formed more easily.
導電性基体上に形成されるトナー層は既にトナー自体の
帯電力行ワれているが必要があれば、コロトロン等ニよ
る強制帯電を行ってもよい。トナー層の厚みは、トナー
粒子が一層乃至数層にわたって形成されるようなもので
あり、その塗布量は単位面積当りの重量で、一般に８乃
至５０ｇ／ｍ”のようなものである。The toner layer formed on the conductive substrate has already been charged by the toner itself, but if necessary, it may be forcibly charged using a corotron or the like. The thickness of the toner layer is such that toner particles are formed in one layer or several layers, and the coating amount is generally 8 to 50 g/m'' in terms of weight per unit area.
画像露光は、フラッシュランプによる全面一様露光や、
ハロゲンランプ等を用いたスリット露光により行うこと
ができる。露光量は、光導電性トナーの感度によっても
大きく変化するが、一般に５０乃至２００１ｕｘ−ｓｅ
ｃの範囲が抵当である。Image exposure includes uniform exposure of the entire surface using a flash lamp,
This can be performed by slit exposure using a halogen lamp or the like. The exposure amount varies greatly depending on the sensitivity of the photoconductive toner, but is generally between 50 and 2001 ux-se.
The range c is the mortgage.
転写手段としては、それ自体公知のコロナ放電転写やロ
ーラ電極による転写を用いることができ、定着操作はそ
の自体公知のヒーター内威圧熱ローラやオーブンヒータ
ーを用いて行うことができる。As the transfer means, corona discharge transfer or roller electrode transfer, which are known per se, can be used, and the fixing operation can be performed using a per se known coercive heat roller in a heater or an oven heater.
定着温度は一般に１６０乃至２００°Ｃの範囲が適当で
ある。The fixing temperature is generally in the range of 160 to 200°C.
（実施例） 以下に、実施例に基づき本発明をより詳細に説明する。(Example) Hereinafter, the present invention will be explained in more detail based on Examples.
実施例１
〔ローダニン誘導体を具備した単量体の合成〕３−アク
リルアミド−５−（Ｐ−ジエチルアミノベンジリデン）
ローダニンの合成
メタクリル酸クロライド１０．４ｇと、３−アミノ−５
−（Ｐ−ジエチルアミノベンジリデン）ローダニン３１
ｇを２００ｍｆのピリジンに溶解し、８０°Ｃで４時間
攪拌反応させた後、生成物をアセトンで再結晶させるこ
とにより上記化合物を得た。Example 1 [Synthesis of monomer with rhodanine derivative] 3-acrylamide-5-(P-diethylaminobenzylidene)
Synthesis of rhodanine 10.4g of methacrylic acid chloride and 3-amino-5
-(P-diethylaminobenzylidene)rhodanine 31
g was dissolved in 200 mf of pyridine, stirred and reacted at 80°C for 4 hours, and the product was recrystallized from acetone to obtain the above compound.
〔光導電性重合体の合成］
３−アクリルアミド−５−（Ｐ−ジエチルアミノベンジ
リデン）ローダニンと（２−Ｎ−カルバゾリルエチル）
アクリレートの共重合
３−アクリルアミド−５−（Ｐ−ジエチルアミノベンジ
リデン）ローダニン３．７ｇと（２−Ｎ−カルバゾリル
エチル）アクリレート２．５ｇに重合開始剤としてアゾ
ビスイソブチロニトリル０゜０５ｇ、溶媒として塩化メ
チレン２０ｍｎを加え、上記混合物を５０ｍ！！、の重
合管に仕込み脱気を数回繰り返し封管法により十分真空
状態としてアンプルを作成した。[Synthesis of photoconductive polymer] 3-acrylamide-5-(P-diethylaminobenzylidene) rhodanine and (2-N-carbazolylethyl)
Copolymerization of acrylate 3.7 g of 3-acrylamide-5-(P-diethylaminobenzylidene) rhodanine and 2.5 g of (2-N-carbazolylethyl)acrylate, 0.05 g of azobisisobutyronitrile as a polymerization initiator, Add 20 ml of methylene chloride as a solvent and mix the above mixture with 50 ml of methylene chloride. ! The mixture was placed in a polymerization tube and degassed several times to create a sufficient vacuum state using the sealing tube method to create an ampoule.
これを６０°Ｃ恒温槽に３０時間浸漬して反応させた後
、メタノールを加えて反応を停止させ塩化メチレンおよ
びメタノールで再沈澱させることにより、５．１ｇの製
法工による本発明の光導電性重合体を得た（分子量はポ
リスチレン換算で１５２００、共重合比はローダニン：
カルバゾール−３ニア）。After immersing this in a 60°C constant temperature bath for 30 hours to react, methanol was added to stop the reaction, and reprecipitation was performed with methylene chloride and methanol. A polymer was obtained (molecular weight was 15,200 in terms of polystyrene, copolymerization ratio was rhodanine:
carbazole-3nia).
定着用樹脂としてスチレン−アクリル共重合体１００重
量部、上記得られた光導電性重合体９０重量部、溶剤と
してトルエン２５００重量部、ＴＨＦ５００重量部から
なる溶液を十分に混合分散し、スプレードライ法によっ
て中心粒子１１μｍの光導電性トナーを得た。このトナ
ーは４８０ｎｍ付近の青色光に光感度を有するトナーで
ある。A solution consisting of 100 parts by weight of a styrene-acrylic copolymer as a fixing resin, 90 parts by weight of the photoconductive polymer obtained above, 2,500 parts by weight of toluene and 500 parts by weight of THF as a solvent was thoroughly mixed and dispersed, and a spray-drying method was applied. A photoconductive toner having a center particle of 11 μm was obtained. This toner is photosensitive to blue light around 480 nm.
次に、１記得られたトナーと電子写真キャリア（フェラ
イトキャリア、平均粒径８０μｍ）とを混合して負に帯
電した（トナー濃度８％）。このトナーをアルミ基板上
に付着させ、青色光で画像形成したところ文字部のヌケ
が無く、地肌カブリのない鮮やかな橙色画像が得られた
。Next, the toner obtained in step 1 and an electrophotographic carrier (ferrite carrier, average particle size: 80 μm) were mixed and negatively charged (toner concentration: 8%). When this toner was deposited on an aluminum substrate and an image was formed using blue light, a bright orange image was obtained with no missing characters and no background fog.
（実施例２）
実施例１で得られた光導電性重合体１００重量部、スチ
レンアクリル共重合体１００重量部、スピロノブラック
１０重量部、溶剤としてトルエン２５００重量部、ＴＨ
Ｆ５０重量部からなる溶液を充分に混合し、スプレード
ライ法により中心粒径１１μｍの光導電性トナーを得た
。(Example 2) 100 parts by weight of the photoconductive polymer obtained in Example 1, 100 parts by weight of styrene-acrylic copolymer, 10 parts by weight of spironoblack, 2500 parts by weight of toluene as a solvent, TH
A solution consisting of 50 parts by weight of F was thoroughly mixed, and a photoconductive toner having a center particle size of 11 μm was obtained by spray drying.
上記得られたトナーと電子写真キャリア（フェライトキ
ャリア、平均粒径８０μｍ）とを混合して負に帯電した
。このトナーをアルミ基板上に付着させ、白色光による
像露光を行い、原稿像に対応する黒色のトナー画像を得
た。得られた画像は地肌カブリのない鮮明なものであっ
た。The toner obtained above and an electrophotographic carrier (ferrite carrier, average particle size 80 μm) were mixed and negatively charged. This toner was deposited on an aluminum substrate and imagewise exposed to white light to obtain a black toner image corresponding to the original image. The obtained image was clear with no background fog.
（発明の効果）
上記実施例からも明らかなように、本発明により得られ
る光導電性トナーは、増感剤や電荷輸送材料等を含有し
なくても可視光領域で優れた光導電性をしめずために、
少ない構成材料で光導電性トナーが得られ、トナー中の
各添加剤の−様な分散が可能となりトナー粒子個々の特
性が均一になる。よって、画像形成に際しても地肌カブ
リのない鮮明な画像が得られる。(Effects of the Invention) As is clear from the above examples, the photoconductive toner obtained by the present invention exhibits excellent photoconductivity in the visible light region even without containing a sensitizer or a charge transport material. For the sake of closure,
A photoconductive toner can be obtained with a small amount of constituent materials, and the additives in the toner can be dispersed in a uniform manner, resulting in uniform properties of the individual toner particles. Therefore, a clear image without background fog can be obtained during image formation.
また、結着樹脂が光導電体でしかも鮮やかな色を呈する
ために、着色剤を含有することなく、透光性にすぐれた
光導電性トナーが得られる。Further, since the binder resin is a photoconductor and exhibits a bright color, a photoconductive toner with excellent translucency can be obtained without containing a colorant.
Claims (1)
記構造式のローダニン誘導体 ▲数式、化学式、表等があります▼ 式中、Ｒは下記一般式 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼ ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼ ▲数式、化学式、表等があります▼ で表される基であり、Ｒ＿１、Ｒ＿２は同一または異な
って、水素原子、アルキル基、置換 または未置換のアリール基を示し、Ｒ＿３は炭素数１〜
６の低級アルキル基、水酸基を 示し、Ｒ＿４は水素原子、炭素数１〜６の低級アルキル
基、置換または未置換のアリー ル基、水酸基を示す、 を具備した光導電性重合体成分を含有することを特徴と
する光導電性トナー。[Claims] In the main chain and/or side chain of the organic polymer photoconductor, there is a rhodanine derivative with the following structural formula ▲ Numerical formula, chemical formula, table, etc. ▼ In the formula, R is the following general formula ▲ Numerical formula, chemical formula , tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. Carbon number 1~
6 represents a lower alkyl group or hydroxyl group, and R_4 represents a hydrogen atom, a lower alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group, or a hydroxyl group. A photoconductive toner characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63146235A JPH022576A (en) | 1988-06-14 | 1988-06-14 | Photoconductive toner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63146235A JPH022576A (en) | 1988-06-14 | 1988-06-14 | Photoconductive toner |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH022576A true JPH022576A (en) | 1990-01-08 |
Family
ID=15403161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63146235A Pending JPH022576A (en) | 1988-06-14 | 1988-06-14 | Photoconductive toner |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH022576A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5696198A (en) * | 1996-01-22 | 1997-12-09 | Electrosorbent, Inc. | Porous electroconductive composite material, and method of manufacturing the same |
-
1988
- 1988-06-14 JP JP63146235A patent/JPH022576A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5696198A (en) * | 1996-01-22 | 1997-12-09 | Electrosorbent, Inc. | Porous electroconductive composite material, and method of manufacturing the same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4311775A (en) | Novel phthalocyanine pigments and electrophotographic uses thereof | |
| US4382033A (en) | Novel phthalocyanine pigments | |
| JPH07234544A (en) | Toner for developing electrostatic charge image | |
| JP3118921B2 (en) | Charge control agent for toner and toner for developing electrostatic images | |
| JPH022576A (en) | Photoconductive toner | |
| US5380615A (en) | Process for producing a toner for development of electrostatic charged image | |
| JPH01147475A (en) | Photoconductive toner | |
| JPH01173065A (en) | Photoconductive toner | |
| JPS63155156A (en) | Production of electrostatic charge developing toner | |
| JPH06332264A (en) | Electrostatic charge image developing toner | |
| JPS6039228B2 (en) | Liquid developer for electrostatography | |
| JPH01173064A (en) | Photoconductive toner | |
| JPH01173068A (en) | Photoconductive toner | |
| KR100419765B1 (en) | Electrostatic toner | |
| JPH01147476A (en) | Photoconductive toner | |
| JPH03132669A (en) | Toner for electrophotography | |
| JPH0762113B2 (en) | Metal complex compound and toner for electrophotography | |
| JPH01173066A (en) | Photoconductive toner | |
| JPH01173067A (en) | Photoconductive toner | |
| JPH01161365A (en) | Photoconductive toner | |
| JPH01150157A (en) | Photoconductive toner | |
| JPH01150156A (en) | Photoconductive toner | |
| JPH01147474A (en) | Photoconductive toner | |
| JP3461046B2 (en) | Positively chargeable toner for developing electrostatic images | |
| JPH01150155A (en) | Photoconductive toner |