GB1008633A - Improved electrophotographic material - Google Patents

Improved electrophotographic material

Info

Publication number
GB1008633A
GB1008633A GB16268/62A GB1626862A GB1008633A GB 1008633 A GB1008633 A GB 1008633A GB 16268/62 A GB16268/62 A GB 16268/62A GB 1626862 A GB1626862 A GB 1626862A GB 1008633 A GB1008633 A GB 1008633A
Authority
GB
United Kingdom
Prior art keywords
reacted
cyclohexanone
ethyl
solution
dissolved
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
Application number
GB16268/62A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Renker Belipa GmbH
Original Assignee
Renker Belipa GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Renker Belipa GmbH filed Critical Renker Belipa GmbH
Publication of GB1008633A publication Critical patent/GB1008633A/en
Expired legal-status Critical Current

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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
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/22—Dyes with unsubstituted amino groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • 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
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
    • 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
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
    • 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
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/062—Acyclic or carbocyclic compounds containing non-metal elements other than hydrogen, halogen, oxygen or nitrogen
    • 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
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0672—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups
    • 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
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0672—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups
    • G03G5/0674—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups containing hetero rings
    • 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
    • G03G5/10—Bases for charge-receiving or other layers
    • 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
    • G03G5/10—Bases for charge-receiving or other layers
    • G03G5/101—Paper bases
    • 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
    • G03G5/10—Bases for charge-receiving or other layers
    • G03G5/102—Bases for charge-receiving or other layers consisting of or comprising metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Emergency Medicine (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

To obtain resinous products which may be used without a binder to form the photoconductive layers of electro-photographic materials various organic photo-conductors are reacted with isocyanate and/or epoxy components. In one embodiment (Example 5) the bisglycidyl ether of ethylene glycol is reacted with 4-[N-ethyl-N-(b -hydroxy ethyl) amino]-benzophenone at 170 DEG C. under nitrogen and the unreacted ether removed under vacuum. The residue is dissolved in cyclohexanone and reacted for a short time at 100% with a modified tri-isocyanate. In another embodiment (Example 8) 3 - amino - a - (41 - dimethylaminocinnamal) -acetophenone is added to an ethyl amyl ketone solution of a partly condensed epoxy resin obtained from diphenol propane and epichlorhydrin, and is reacted under reflux at 100 DEG C. To form a photoconductive layer the reaction mixture is diluted with methyl isobutyl ketone and methyl ethyl ketone and a small quantity of a modified tri-isocyanate added with sensitizing dyes-the mixture is coated on to a support and the solvents allowed to evaporate. In a further embodiment (Example 4) a cyclohexanone solution of 2-hydroxy-4-diethylamino - 21 - carboxy - benzophenone (containing a small amount of Rhodamine B) is mixed with a concentrated solution in ethyl acetate of a modified triisocyanate obtained by reacting 1 mol of tri-methylol propane and 3 mol of toluylene-2: 4 and/or 2: 6-diisocyanate. Condensation is effected at 151 DEG C. and the product thrown out of solution by the addition of acetone. In a further embodiment (Example 7) 2 - hydroxy - 4 - dimethylamino - a - [4 - (methylb -hydroxyethy - amino) - cinnamal] - acetophenone and a concentrated ethyl acetate solution of a modified triisocyanate are dissolved in cyclohexanone and reacted at 150 DEG C. The reaction mixture is diluted with methyl ethyl ketone and ethyl amyl ketone to form the coating composition. In another embodiment (Example 9) an isocyanate component is made by the reaction at 148 DEG C. of 2-ethyl-2-butylpropan-1 : 3-diol with toluylene-2: 4-(or 2: 6)-diisocyanate. The purified product is dissolved in cyclohexanone with 4-dimethylamino-phenyl-31-hydroxy-naphthyl-(21)-ketone and condensed at 135 DEG C. to obtain a solution of the photo-conductive product. In another embodiment (Example 17) a concentrated ethyl acetate solution of a modified tri-isocyanate is dissolved in cyclohexanone with 2: 4-di-hydroxybenzophenone, and initially reacted under reflux at 150 DEG C. The temperature is then mixed to 200 DEG C.-the cyclohexanone distills off. The resin left is dissolved in mixed solvents to obtain the coating composition.ALSO:<FORM:1008633/C2/1> <FORM:1008633/C2/2> <FORM:1008633/C2/3> In Examples (6), (12) and (16), the trisiso-cyanate obtained from trimethylolpropane (1 mol.) and tolylene diisocyanate (3 mols.) is reacted with the compounds of the formulae given in Figs. 8, 23 and 21 respectively. In Example (12), n-dodecyl alcohol is also present. The product of Example (16) is further reacted with di-(2-ethylhexyl) amine.
GB16268/62A 1961-04-29 1962-04-27 Improved electrophotographic material Expired GB1008633A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DER30222A DE1246407B (en) 1961-04-29 1961-04-29 Photoconductive layer

Publications (1)

Publication Number Publication Date
GB1008633A true GB1008633A (en) 1965-11-03

Family

ID=7403228

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16268/62A Expired GB1008633A (en) 1961-04-29 1962-04-27 Improved electrophotographic material

Country Status (4)

Country Link
US (1) US3265497A (en)
BE (1) BE617032A (en)
DE (1) DE1246407B (en)
GB (1) GB1008633A (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE626529A (en) * 1961-12-29
US3352670A (en) * 1964-02-14 1967-11-14 Minnesota Mining & Mfg Supersensitizers for optically sensitized photoconductive layers
US3493369A (en) * 1964-04-03 1970-02-03 Appleton Coated Paper Co Low electrical resistance varnish coatings on an insulating base
US3526501A (en) * 1967-02-03 1970-09-01 Eastman Kodak Co 4-diarylamino-substituted chalcone containing photoconductive compositions for use in electrophotography
US3533787A (en) * 1967-07-31 1970-10-13 Eastman Kodak Co Photoconductive elements containing polymeric binders of nuclear substituted vinyl haloarylates
US3652269A (en) * 1968-08-27 1972-03-28 Eastman Kodak Co Photoconductive elements containing halogenated polyethylene binders
US3994724A (en) * 1969-07-23 1976-11-30 Scott Paper Company Photoconductor elements containing substituted aniline photoconductor compounds
US3873311A (en) * 1973-05-04 1975-03-25 Eastman Kodak Co Aggregate photoconductive compositions and elements containing a styryl amino group containing photoconductor
US3873312A (en) * 1973-05-04 1975-03-25 Eastman Kodak Co Photoconductive composition and elements containing a styryl amino group containing photoconductor
DE2734289C2 (en) 1977-07-29 1982-06-09 Hoechst Ag, 6000 Frankfurt Photoconductor tape
CH637922A5 (en) * 1978-09-22 1983-08-31 Ciba Geigy Ag CHROMOGENIC PROPENYLENE SULPHONE COMPOUNDS.
JP2817822B2 (en) * 1992-05-14 1998-10-30 富士電機株式会社 Electrophotographic photoreceptor
JPH06312961A (en) * 1993-04-28 1994-11-08 Takasago Internatl Corp 1,4-bis(4,4-diphenyl-1, 3-butadienyl)benzene derivative and electrophotographic photoreceptor using the same
DE19917906A1 (en) * 1999-04-20 2000-10-26 Basf Ag Use of amino-substituted hydroxybenzophenones as photostable UV filters in cosmetic and pharmaceutical preparations

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2710274A (en) * 1952-03-26 1955-06-07 Kuehl Georg Walter Multi-layer glass sheet
DE1060712B (en) * 1956-07-04 1959-07-02 Kalle & Co Ag Material for electrophotographic reproduction
BE562336A (en) * 1956-11-14
LU35567A1 (en) * 1956-11-21
BE568418A (en) * 1957-06-08
US3155503A (en) * 1959-02-26 1964-11-03 Gevaert Photo Prod Nv Electrophotographic material
NL250327A (en) * 1959-04-08
DE1216690B (en) * 1960-10-03 1966-05-12 Renker Belipa G M B H Photoconductive layer for an electrophotographic recording material

Also Published As

Publication number Publication date
DE1246407B (en) 1967-08-03
US3265497A (en) 1966-08-09
BE617032A (en)

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