US3799773A - Electrophotographic process employing a photochromic compound and transparent toner - Google Patents
Electrophotographic process employing a photochromic compound and transparent toner Download PDFInfo
- Publication number
- US3799773A US3799773A US00219121A US21912172A US3799773A US 3799773 A US3799773 A US 3799773A US 00219121 A US00219121 A US 00219121A US 21912172 A US21912172 A US 21912172A US 3799773 A US3799773 A US 3799773A
- Authority
- US
- United States
- Prior art keywords
- chromene
- toner
- image
- indoline
- photochromic compound
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title abstract description 40
- 238000000034 method Methods 0.000 title abstract description 30
- 230000015572 biosynthetic process Effects 0.000 abstract description 12
- 238000004040 coloring Methods 0.000 abstract description 8
- 239000011347 resin Substances 0.000 description 29
- 229920005989 resin Polymers 0.000 description 29
- 239000000463 material Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229920002689 polyvinyl acetate Polymers 0.000 description 12
- 239000004793 Polystyrene Substances 0.000 description 10
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 10
- 239000004926 polymethyl methacrylate Substances 0.000 description 10
- -1 aromatic carboxylic acids Chemical class 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 239000000049 pigment Substances 0.000 description 7
- 239000011118 polyvinyl acetate Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229920002284 Cellulose triacetate Polymers 0.000 description 6
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 6
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- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- 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 2
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 2
- 239000005033 polyvinylidene chloride Substances 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229960001755 resorcinol Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- PSXPTGAEJZYNFI-UHFFFAOYSA-N 1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole] Chemical compound O1C2=CC=C([N+]([O-])=O)C=C2C=CC21C(C)(C)C1=CC=CC=C1N2C PSXPTGAEJZYNFI-UHFFFAOYSA-N 0.000 description 1
- 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
- NLOLPAQEEFKZKP-UHFFFAOYSA-N 1-ethenyl-1,2-dihydroacenaphthylene Chemical compound C1=CC(C(C=C)C2)=C3C2=CC=CC3=C1 NLOLPAQEEFKZKP-UHFFFAOYSA-N 0.000 description 1
- UVHXEHGUEKARKZ-UHFFFAOYSA-N 1-ethenylanthracene Chemical compound C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 UVHXEHGUEKARKZ-UHFFFAOYSA-N 0.000 description 1
- IMZNOWXSCHXDLC-UHFFFAOYSA-N 1-ethenylperylene Chemical group C1=CC(C=2C(C=C)=CC=C3C=2C2=CC=C3)=C3C2=CC=CC3=C1 IMZNOWXSCHXDLC-UHFFFAOYSA-N 0.000 description 1
- VRIRHHMUAHTQFJ-UHFFFAOYSA-N 1-ethenyltetracene Chemical compound C1=CC=C2C=C(C=C3C(C=C)=CC=CC3=C3)C3=CC2=C1 VRIRHHMUAHTQFJ-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
- DMMLPQQNXDSSNN-UHFFFAOYSA-N 3'-ethyl-1',3'-dimethyl-6-nitrospiro[chromene-2,2'-indole] Chemical compound O1C2=CC=C([N+]([O-])=O)C=C2C=CC21N(C)C1=CC=CC=C1C2(C)CC DMMLPQQNXDSSNN-UHFFFAOYSA-N 0.000 description 1
- JXQCUCDXLSGQNZ-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methylbenzoic acid Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1C(O)=O JXQCUCDXLSGQNZ-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 229920000390 Poly(styrene-block-methyl methacrylate) Polymers 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
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 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
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 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
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 235000010187 litholrubine BK Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- XRARAKHBJHWUHW-QVUBZLTISA-N neoline Chemical compound O[C@@H]1[C@H]2[C@@H]3[C@@]4([C@@H]5[C@H]6OC)[C@@H](O)CC[C@@]5(COC)CN(CC)C4[C@H]6[C@@]2(O)C[C@H](OC)[C@H]1C3 XRARAKHBJHWUHW-QVUBZLTISA-N 0.000 description 1
- HTSYYNWISWGUIR-UHFFFAOYSA-N neoline Natural products CCN1CC2(COc3ccccc3)CCC(O)C45C6CC7C(CC(O)(C6C7O)C(C(OC)C24)C15)OC HTSYYNWISWGUIR-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- XRARAKHBJHWUHW-UHFFFAOYSA-N subcusine Natural products OC1C2C3C4(C5C6OC)C(O)CCC5(COC)CN(CC)C4C6C2(O)CC(OC)C1C3 XRARAKHBJHWUHW-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber 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
- G03G13/00—Electrographic processes using a charge pattern
- G03G13/06—Developing
- G03G13/08—Developing using a solid developer, e.g. powder developer
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
-
- 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
-
- 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
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08713—Polyvinylhalogenides
- G03G9/08715—Polyvinylhalogenides containing chlorine, bromine or iodine
-
- 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
- G03G9/087—Binders for toner particles
- G03G9/08775—Natural macromolecular compounds or derivatives thereof
- G03G9/08777—Cellulose or derivatives thereof
-
- 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
- G03G9/0906—Organic dyes
- G03G9/091—Azo dyes
-
- 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
- G03G9/0906—Organic dyes
- G03G9/0918—Phthalocyanine dyes
-
- 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
- G03G9/0906—Organic dyes
- G03G9/092—Quinacridones
-
- 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
-
- 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
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09733—Organic compounds
- G03G9/09775—Organic compounds containing atoms other than carbon, hydrogen or oxygen
Definitions
- This invention relates to a new process for the formation of images.
- Photochromic compounds which absorb light and repeat a reversible color change
- These compounds maintain in general stable colorless state without the influence of exciting light such as ultraviolet rays. On irradiating ultraviolet rays thereto, they change into a colored state of different absorption spectrum. The molecules under such colored state return readily to the original colorless state due to their instabilities when the exciting light is removed.
- photo-coloring and -discoloring materials utilizing such reversibility, vice versa, owing to the characteristics said photo-coloring and -discoloring materials exhibit using the photochromic compound could not be preserved as permanent images though they are able to be used for copying temporary images. Further, because the color shade is monochromic, it was impossible to form multi-color images though a shading image might be obtained.
- a photochromic compound is contained in an electrophotographic sensitive layer, whereby a sensitive material is obtained which is a photo-coloring and -discoloring material and has characteristics of an electrophotographic material, whereas the photochromic compound is dispersed in a resinous binder in the previous sensitive material containing the photochromic compound.
- said sensitive material is charged electrically in the dark and then exposed image-wise to form a permanent image whereby it is colored by means of ultraviolet rays in quite the same manner as in the previous method and discolored by means of heat or visible rays.
- the exposure time may be very short because theelectrophotographic sensitivity is much higher than the photosensitivity of photochromism. It is then further treated according to the electrophotographic process of this in-- vention to yield a toner image thereon. If a substance which shows a peculiar interaction with the components in the sensitive layer is selected as a material for forming 3,799,773 Patented Mar. 26, 1974 the toner image, a new copying process is realized as described in detail hereinafter.
- resin toners there may be used resins which are not preferable as binders for the photochromic sensitive material, e.g. polyvinyl chloride, polyvinylidene chloride, vinyl chloride/vinyl acetate copolymer, polyhydroxyethylmethacrylate and polyvinylpyrrolidone.
- resins which are not preferable as binders for the photochromic sensitive material e.g. polyvinyl chloride, polyvinylidene chloride, vinyl chloride/vinyl acetate copolymer, polyhydroxyethylmethacrylate and polyvinylpyrrolidone.
- the sensitive layer is mixed with the toner layer to yield a colored positive image even in the dark.
- the non-imaged area may be colored by the whole surface exposure.
- toners there are mentioned for example cellulose acetate, ethyl cellulose, cellulose acetate butylate, cellulose acetate phthalate etc.
- toners there are mentioned mixtures of resins such as polystyrene, polyvinyl acetate and polymethacrylate with a third substance.
- resins such as polystyrene, polyvinyl acetate and polymethacrylate
- third substances there are preferably compounds having a large polarity which are different from that of said resins with preference for aromatic carboxylic acids and phenols but which are not restricted only to these compounds.
- phthalic acid benzoic acid, nitrobenzoic acid, chlorobenzoic acid, oxybenzoic acid, salicylic acid, toluylic acid, naphthoic acid, anthranilic acid, anisic acid, nitrophenol, naphthol, picric acid, chlorophenol oxyacetophenone, resorcin, hydroquinone, oxybenzophenone etc.
- the color of image area may be varied according to the preference and converted into a positive image, in which the non-imaged area is colored, by the whole surface exposure to ultraviolet rays.
- the toners to be used thereto are not restricted to resins of (i)(iii) and they may be used as toners by adding colored pigment or colorants to these resins.
- the following pigments or coloring mat-j ters are selected resulting in giving any desired colored toner:
- Red Brilliant Carmine 6B, Quinacridone Red, Oil red.
- Phthalocyanine Blue Phthalocyanine Green.
- the combination of photochromic compound and toner resin can provide any desired color image, occasionally resulting in a variously varying shade of tonered area.
- a monochromic or multi-color image is obtained by utilizing the function of said four kinds of toners; for example, a sensitive material is treated first with a toner of the group (i), the material carrying the first toner image is again charged in the dark and imagewise exposed to yield the second latent image, which is then developed with a toner of the group (ii), resulting in an image which consists of three areas of different shades, i.e. the non-imaged area, the first toner image area (colorless) and the second toner image area (the second shade different from that of the non-imaged area).
- the first toner image area when the toner is highly insulating, is charged at a high voltage and the light decay is rather delayed, so that the second toner may be apt to strongly adhere again to the first toner image area (in the positive-positive development). This gives no influence to the shade of image at all providing no problem where the second toner is also colorless.
- the photochromic compound contained in the sensitive layer of this invention not only behaves to provide an imlage of more than one color in the development but sensitizes the photosensitivity of a photoconductor such as poly-N-vinyl carbazole, i.e. behaves as a sensitizer.
- a photoconductor such as poly-N-vinyl carbazole
- photochromic compounds to be used in this invention there are mentioned those represented by the following general formula:
- R represents alkyl radical ha ving 1-5 carbon atoms, substituted alkyl (substituent: carboxyl, cyano or ester group) or phenyl radical
- R and R represent alkyl radical having 1-5 carbon atoms or phenyl radical or may form together
- X represents hydrogen atom, nitro group, halogen atom; hydroxycarbonyl and alkoxycarbonyl group, alkyl radical ha'ving 1-5 carbon atoms or alkoxy group
- Y represents at least more than one of hydrogen atom, nitro group, halogen atom, aldehyde group and alkoxy group.
- Polynucleus aromatic vinyl polymers are polynucleus aromatic vinyl polymers :"poI'ym'ers of vinyl naphthalene, vinyl anthracene, vinyl diphenyl, vinyl :fiuorene, vinyl acenaphthene, vinyl -p'yrene, vinyl naphthacene, vinyl perylene etc.
- Vinyl polymers having a heterocyclic side chain polyvinylcarbazole, polyvinylphenothiazine, polyvinylacridine, polyacryloylcarbazole," .polyvinylbenzofuran, polyvinylpyrazoline, polyvinyloxazole, polyvinyl-fluorine etc.
- the amount of the photochromic compound to be used in this invention is 01-10% by weight referred to the photoconductive resin, above all preferably 25%.
- the solution of V photochfomi'c compound and photoconductive resin dissolved in a suitable organic solvent is coated on a support such as transparent film or paper, etc., which is subjected to the conduction treatment, and dried.
- a support such as transparent film or paper, etc.
- the product which is obtained by the process according to this invention may be applied to the multicolor copy, display, original for overhead projector, decoration film, etc. and is considerably excellent for fixing of photochromic sensitive material.
- EXAMPLE 1 A solution consisting of 1 part of 1,3,3-trimethyl-5- ethoxycarbonyl-6'-nitrospiro(indoline 2,2 Z'H-chromene) and 50 parts of toluene solution of poly-N- vinylcarbazole was coated on a polyethylene terephthalate film providedwith a transparent conductive undercoat so that the dry film thickness may be 10 1..
- the film is ordinarily colorless and transparent.
- the sensitive layer may be'used in the following two ways:
- a transparent negative image film is contacted to the layer and irradiated for 30 sec. by an ultraviolet lamp (Toshiba 'SI IL-IOO, manufactured by Tokyo Shibaura Electric Co.,Ltd.) at a distance of 15 cm. to yield a positive image which is colored only in the areas through which ultraviolet rays have passed. If it is stood in the dark or heated at C., it returns to a colorless transparent film.
- an ultraviolet lamp Toshiba 'SI IL-IOO, manufactured by Tokyo Shibaura Electric Co.,Ltd.
- the colorless film is charged positive in the dark, contacted with a transparent positive image film, exposed for 2.secs. by a 20 w. fluorescent lamp (Toshiba Neoline FL -ZOS, Manufactured by Tokyo Shibaura Electric Co., Ltd.) at a distance of 15 cm. and developed with a liquid colorless toner developer having a negative charge (e.g., liquid developer containing polyvinyl chloride as a toner) to yield a positive image in which the areas provided with the toner are opaque.
- a liquid colorless toner developer having a negative charge e.g., liquid developer containing polyvinyl chloride as a toner
- Example 1 belongs to the above mentioned-classificat ion (i).
- EXAMPLE 2 A solution consisting of 1 part of 1,3,3-trimethyl-6'- nitrospiro (indoline-2,2-2'H-chromene) and 50 parts of 20% toluene solution of poly-N-vinylcarbazole is coated on a polyethylene terephthalate film provided with a transparent conductive undercoat so that the dry film thickness may be 10p. It shows the previousphotochromism.
- Example 2 The film is further charged in the same manner asin Example 1 accordingto the electrophotographic process, exposed imagewise, developed with a cellulose triacetate toner and fixedin theatmosphere of trichloroethylene to yieldan image inwhich the image area is red and the non-imaged area colorless. If it is over-all'exposed to ultraviolet rays, the non-imaged area becomes dark blue and the image area reddish violet.
- This example belongs to theaboveclassification (ii). .In this example, the variation of toner components (additives and resin) provided the results as shown in the following table.
- PS X Pl ⁇ 4MA Polymethylmethacrylate.
- PVAc Polyvinyl acetate. I TAG Cellulose triacetate.
- l PS Polystyrene. 5
- Tlnuvin 326 Ultravio1et absorber manufactured by Geigy Co.
- Uvinul M-40 Ultraviolet absorber manufactured by GAF Co. 7
- colorless means colorless and transparent.”
- EXAMPLE 3 The sensitive material obtained in Example 1 is developed with a toner of p-oxybenzoic acid and polymethylmethacrylate, fixed and over-all exposed to ultraviolet rays, whereby the nonimaged area is colored blue and the image area pink. It turns to colorless and transparent on heating at 80 C.
- This example belongs to the above classification (iii).
- EXAMPLE 4 A solution consisting of 1 part of l,3,3-trimcthyl -51 methoxy-6'-nitrospiro (indoline-Z,2'-2'H-chromene) and 50 parts of toluene solution of polyacenaphthylene is coated on a polyethylene terephthalate film provided with a transparent conductive under-coat so that the dry film thickness may be 10;, and dried to yield a transparent film, which shows of course the previous photochromism. The film is charged and exposed in the same manner as in Example 1, cascade-developed with a blue toner and fixed to yield a positive image. I
- This example belongs to the above classification (iv).
- a process for the formation of a toner image by an electrophotographic process comprising the steps of:
- said photochromic compound is a compound represented by the general formula wherein R represents alkyl having 1-5 carbon atoms, substituted alkyl wherein said substituents are carboxyl, cyano or ester groups, or phenyl; R and R are alkyl having 1-5 carbon atoms, phenyl or they form together (CH n is 4 or 5, X represents hydrogen, nitro, halogen, hydroxycarbonyl, alkoxycarbonyl, alkyl having 1-5 carbon atoms or alkoxy; and Y represents at least more than one of hydrogen, nitro, halogen, aldehyde and alkoxy.
- said toner comprises a combination of a resin and an additive which together are capable of interacting with said photochromic compound upon contact to cause said photochromic compound to change color.
- said toner is a resin selected from the group consisting of polymethylmethacrylate, polyvinylacetate and cellulose triacetate.
- said toner is a resin selected from the group consisting of polymethylmethacrylate, polyvinylacetate, cellulose triacetate and polystyrene together with an additive selected from the group consisting of p-oxybenzoic acid, p-nitrophenol and carbon tetrabromide.
- a process for the formation of image according to claim 1 characterized in that a resin which hinders the color-development of said photochromic compound is used as the resin toner.
- a process for the formation of image according to claim 12 characterized in that as said resin toner there is used polyvinyl chloride, polyvinylidene chloride, vinyl chloride/vinyl acetate copolymer, polyhydroxyethylmethacrylate or polyvinyl-pyrrolidone.
- a process for the formation of image according to claim 15 characterized in that polystyrene, polyvinyl acetate or polymethacrylic acid ester is used as said resin.
- said compound is selected from the group consisting of phthalic acid, benzoic acid, nitrobenzoic acid, chlorobenzoic acid, oxybenzoic acid, salycilic acid, toliylic acid, naphthoic acid, anthranilic acid, anisic acid, nitrophenol, naphthol, picric acid, chlorophenol, oxyacetophenone, resorcin, hydroquinone or oxybenzophenone.
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Developing Agents For Electrophotography (AREA)
- Combination Of More Than One Step In Electrophotography (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46001322A JPS5121345B1 (enrdf_load_stackoverflow) | 1971-01-19 | 1971-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3799773A true US3799773A (en) | 1974-03-26 |
Family
ID=11498241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00219121A Expired - Lifetime US3799773A (en) | 1971-01-19 | 1972-01-19 | Electrophotographic process employing a photochromic compound and transparent toner |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3799773A (enrdf_load_stackoverflow) |
| JP (1) | JPS5121345B1 (enrdf_load_stackoverflow) |
| CA (1) | CA964093A (enrdf_load_stackoverflow) |
| DE (1) | DE2202497A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2122913A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1378572A (enrdf_load_stackoverflow) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3999989A (en) * | 1970-12-19 | 1976-12-28 | Fuji Photo Film Co., Ltd. | Electrophotographic member having improved sensitizer and process utilizing same |
| US4142982A (en) * | 1975-06-04 | 1979-03-06 | Canon Kabushiki Kaisha | Toner for developing electrostatic latent images comprising resin binder of polyester and solid silicone varnish |
| US4756985A (en) * | 1984-08-30 | 1988-07-12 | Konishiroku Photo Industry Co., Ltd. | Method of forming multicolor images |
| US5260753A (en) * | 1990-11-14 | 1993-11-09 | Konica Corporation | Color image forming method |
| WO1995004955A1 (en) * | 1993-08-05 | 1995-02-16 | Kimberly-Clark Corporation | Mutable composition and methods of use thereof |
| US5616443A (en) | 1993-08-05 | 1997-04-01 | Kimberly-Clark Corporation | Substrate having a mutable colored composition thereon |
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|---|---|---|---|---|
| US4375492A (en) * | 1981-05-22 | 1983-03-01 | Appleton Papers Inc. | Dielectric record material |
| US5405726A (en) * | 1991-11-11 | 1995-04-11 | Bando Chemical Industries. Ltd. | Method and apparatus for decolorization, and image forming apparatus |
| US5358814A (en) * | 1993-08-31 | 1994-10-25 | Eastman Kodak Company | Toner compositions containing as a negative charge-controlling agent a mixture of ortho-benzoic sulfimide and para-anisic acid |
-
1971
- 1971-01-19 JP JP46001322A patent/JPS5121345B1/ja active Pending
-
1972
- 1972-01-17 FR FR7201438A patent/FR2122913A5/fr not_active Expired
- 1972-01-18 CA CA132,653A patent/CA964093A/en not_active Expired
- 1972-01-19 US US00219121A patent/US3799773A/en not_active Expired - Lifetime
- 1972-01-19 GB GB266372A patent/GB1378572A/en not_active Expired
- 1972-01-19 DE DE19722202497 patent/DE2202497A1/de active Pending
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| US6168654B1 (en) | 1996-03-29 | 2001-01-02 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
| US6099628A (en) | 1996-03-29 | 2000-08-08 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
| US6524379B2 (en) | 1997-08-15 | 2003-02-25 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
| US6503559B1 (en) | 1998-06-03 | 2003-01-07 | Kimberly-Clark Worldwide, Inc. | Neonanoplasts and microemulsion technology for inks and ink jet printing |
| US6277897B1 (en) | 1998-06-03 | 2001-08-21 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
| US6228157B1 (en) | 1998-07-20 | 2001-05-08 | Ronald S. Nohr | Ink jet ink compositions |
| US6265458B1 (en) | 1998-09-28 | 2001-07-24 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
| US6368396B1 (en) | 1999-01-19 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
| US6331056B1 (en) | 1999-02-25 | 2001-12-18 | Kimberly-Clark Worldwide, Inc. | Printing apparatus and applications therefor |
| US6294698B1 (en) | 1999-04-16 | 2001-09-25 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
| US6368395B1 (en) | 1999-05-24 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Subphthalocyanine colorants, ink compositions, and method of making the same |
| US10723883B2 (en) * | 2015-06-10 | 2020-07-28 | Council Of Scientific And Industrial Research | Spiropyran based composition and application thereof as security tag |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2202497A1 (de) | 1972-08-03 |
| JPS5121345B1 (enrdf_load_stackoverflow) | 1976-07-01 |
| GB1378572A (en) | 1974-12-27 |
| CA964093A (en) | 1975-03-11 |
| FR2122913A5 (enrdf_load_stackoverflow) | 1972-09-01 |
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