US3549358A - Electrophotographic process using organic photoconductors having at least two chromophores - Google Patents

Electrophotographic process using organic photoconductors having at least two chromophores Download PDF

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Publication number
US3549358A
US3549358A US786461A US3549358DA US3549358A US 3549358 A US3549358 A US 3549358A US 786461 A US786461 A US 786461A US 3549358D A US3549358D A US 3549358DA US 3549358 A US3549358 A US 3549358A
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United States
Prior art keywords
percent
bis
compounds
photoconductive
prepared
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Expired - Lifetime
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US786461A
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English (en)
Inventor
Nicholas J Clecak
Robert J Cox
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International Business Machines Corp
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International Business Machines Corp
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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
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
    • G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
    • G03G5/065—Heterocyclic compounds containing two or more hetero rings in the same ring system containing three relevant rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
    • 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
    • G03G5/0612—Acyclic or carbocyclic compounds containing 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
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
    • G03G5/0661—Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring
    • 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
    • G03G5/0675—Azo dyes
    • G03G5/0677—Monoazo dyes
    • 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
    • G03G5/0675—Azo dyes
    • G03G5/0679—Disazo dyes

Definitions

  • the organic photoconductors are certain linear molecules having at least two chromophores such as a Schiffs base group or an azo group joined to one another through a benzene ring or series of benzene rings. These compounds have been found to be useful as photocondnctors in electrophotographic processes. Some of the compounds are novel.
  • This invention relates to a class of organic photoconductive materials and, more particularly, relates to their use as photocondnctors in electrophotographic processes, especially those utilizing contact reflex exposure.
  • the compounds of the general formula are dissolved in organic solvents, such as tetrahydrofuran, or any other solvent in which the compounds are at least partially soluble.
  • organic solvents such as tetrahydrofuran, or any other solvent in which the compounds are at least partially soluble.
  • Such solutions are applied to substrates suitable for electrophotography and the solvent is then removed. Mixtures of solvents can also be used.
  • Suitable resins include both natural and synthetic resins, examples of which are balsam resins, phenol resins modified with colophony, coumarone resins, indene resins, cellulose ethers, polyvinylchlorides, polyvinylacetate, acrylic polymers, such as polymethyl acrylic esters, polystyrene, polyisobutylene, polyvinylnormal, polycondensates, such as phthalate resins, polyamides, and polyadducts, such as polyurethanes.
  • the proportion of resin to the photoconductive compound can vary greatly, but elements having a high proportion of resin and a low proportion of photoconductive compound are the less desired. Mixtures of at least equal parts resin and photoconductive compound are preferred.
  • the substrate material may be any which satisfy the requirements of electrophotography such as metal, glass, paper, or plastic. Unless it is to be used in a device employing dual corona discharge, such as US. Pat. 2,922,883, the substrate should preferably have a conductivity greater than 10- ohm cm.-
  • xerography One type of electrophotographic process in which the compounds of the present invention are useful is known as xerography.
  • the process comprises the laying down of the uniform electrostatic charge on a photoconductive and insulating element, exposing the electrostatic charge surinto contact with the developed image and transferred I thereto and fixed thereon.
  • the residual toner remaining on the photoconductive insulating element is removed by cleaning and the element is then ready for the preparation of the next copy or the next cycle.
  • the compounds of the present invention are suitable for use in that type of electrophotography known as contact reflex reproduction, which is an electrophotographic process for the production of related as a yellow crystalline solid as shown in Beil., 14, 35. It had the following analysis.
  • EMMPLE II 1,4 bis benzylidene bis N,N dimethyl-p-phenylenediamine flex copies in which a document is positioned adjacent a photoconductive element which exhibits photoconductive dichroism and has a preferred absorption axis, and in which the photoconductive element is uniformly exposed through the photoconductive element with polarized light whose vector, relative to the absorption axis, is such that the light is not absorbed.
  • the polarized light in striking the document is absorbed in some areas, nor- CHa and, hence, permits the formation of an electrostatic charge pattern corresponding to the document.
  • a general method for the preparation of the Schitfs base type of condensation product is as follows:
  • the difunctional aldehyde or diamine is dissolved in an alcohol such as n-butanol with a slight excess of the mono functional aldehyde or amine and heated to reflux for 6-2 hours.
  • the resultant condensation products precipitate out of the hot reaction solvent and are hot filtered. They are subsequently washed with acetone, ether, 55
  • EXAMPLE VII N,N' bis (9-julolidinidene) benzidine CHzCHzCHz CHaCHz (EH3 Prepared by the general procedure refluxing 9-formyl- '1 g. 4,4 diaminostilbene and 3 g. p-N,N-dimethylaminojulolidene and benzidine in n-butanol for two hours. Isocinnamaldehyde in 150 ml. n-butanol were refluxed for lated as yellow solids. 45 minutes. The resulting precipitate was hot filtered and Calcd. for C H N (percent): C, 82.8; H, 6.9; N, washed with acetone, ether and dried. Recovered 0.75 g.
  • a photoconductive element was prepared by dispers- 4,4 (bis p-nitrocinnamylidene) benzidine ing N,N' bis(p-dimethylaminophenylazobenzilidine)ben- 0.45 g. benzidine and 1.5 g. p-nitrocinnamaldehyde in zidine (the compound of Example VIII above) in an 100 ml. n-butanol were refluxed for 1 hour. The resultequal weight of polystyrene dissolved in 1,2-dichloroething precipitate was hot filtered and washed with acetone, ane and coating the solution on an aluminum slide with ether and dried.
  • the toner After transfer of the toner 4,4 -bis (p-dimethylaminocinnamylideneamino) stilbene image, the toner was fused to the paper on a hot plate CH3 CH3 CH3 CH3 7 to yield a high quality copy of the document with high contrast, high image density, and faint background.
  • the photoconductive element comprises a compound selected from the group consisting of compounds having the formula:
  • A is selected from the group consisting of CH2CH2 X is selected from the group consisting of:

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Light Receiving Elements (AREA)
US786461A 1968-12-23 1968-12-23 Electrophotographic process using organic photoconductors having at least two chromophores Expired - Lifetime US3549358A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US78646168A 1968-12-23 1968-12-23

Publications (1)

Publication Number Publication Date
US3549358A true US3549358A (en) 1970-12-22

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US786461A Expired - Lifetime US3549358A (en) 1968-12-23 1968-12-23 Electrophotographic process using organic photoconductors having at least two chromophores

Country Status (4)

Country Link
US (1) US3549358A (enrdf_load_stackoverflow)
DE (1) DE1963197A1 (enrdf_load_stackoverflow)
FR (1) FR2026846A1 (enrdf_load_stackoverflow)
GB (3) GB1296862A (enrdf_load_stackoverflow)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3884691A (en) * 1972-09-21 1975-05-20 Hoechst Ag Electrophotographic element of azo dye layer and charge transport overlayer
US3977870A (en) * 1972-09-21 1976-08-31 Hoechst Aktiengesellschaft Dual layer electrophotographic recording material
US4026704A (en) * 1971-12-08 1977-05-31 Hoechst Aktiengesellschaft Electrophotographic recording material
US4047944A (en) * 1976-06-01 1977-09-13 Eastman Kodak Company Electrophoretic migration imaging process with neutral density bisazo pigments
US4072520A (en) * 1972-08-30 1978-02-07 Hoechst Aktiengesellschaft Electrophotographic dual layer recording material
US4123270A (en) * 1975-09-15 1978-10-31 International Business Machines Corporation Method of making electrophotographic imaging element
US4299896A (en) * 1977-07-18 1981-11-10 Ricoh Co., Ltd. Electrophotographic sensitive materials containing a disazo pigment
US4841009A (en) * 1982-12-28 1989-06-20 Amoco Corporation Substantially linear monomeric composition and liquid crystal polymeric compositions derived therefrom
US5262330A (en) * 1992-02-27 1993-11-16 Miles Inc. Colorimetric methods and reagents for the assay of calcium in a test sample
US20060147652A1 (en) * 2004-12-31 2006-07-06 Industrial Technology Research Institute Dichroic dye and microencapsulated liquid crystal composition thereof

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6029944B2 (ja) * 1978-12-13 1985-07-13 株式会社リコー 積層型電子写真感光体及びその製造方法
JPS5584943A (en) * 1978-12-21 1980-06-26 Ricoh Co Ltd Laminated type electrophotographic photoreceptor
FR2707635B1 (fr) * 1993-06-29 1995-08-25 Cray Valley Sa Diamines aromatiques thermotropes à jonctions imines, leur procédé de synthèse et leur application à l'obtention de polyurées thermotropes.

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3066023A (en) * 1958-12-19 1962-11-27 Azoplate Corp Member for electrophotographic reproduction and process therefor
US3163532A (en) * 1960-09-17 1964-12-29 Azoplate Corp Material for electrophotographic purposes
US3335003A (en) * 1963-10-09 1967-08-08 Xerox Corp Reflex xerographic process
US3489558A (en) * 1967-09-18 1970-01-13 Ibm Photoconductive benzobisthiazoles and their use in electrophotographic processes

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3066023A (en) * 1958-12-19 1962-11-27 Azoplate Corp Member for electrophotographic reproduction and process therefor
US3163532A (en) * 1960-09-17 1964-12-29 Azoplate Corp Material for electrophotographic purposes
US3335003A (en) * 1963-10-09 1967-08-08 Xerox Corp Reflex xerographic process
US3489558A (en) * 1967-09-18 1970-01-13 Ibm Photoconductive benzobisthiazoles and their use in electrophotographic processes

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4026704A (en) * 1971-12-08 1977-05-31 Hoechst Aktiengesellschaft Electrophotographic recording material
US4072520A (en) * 1972-08-30 1978-02-07 Hoechst Aktiengesellschaft Electrophotographic dual layer recording material
US3884691A (en) * 1972-09-21 1975-05-20 Hoechst Ag Electrophotographic element of azo dye layer and charge transport overlayer
US3977870A (en) * 1972-09-21 1976-08-31 Hoechst Aktiengesellschaft Dual layer electrophotographic recording material
US4123270A (en) * 1975-09-15 1978-10-31 International Business Machines Corporation Method of making electrophotographic imaging element
US4047944A (en) * 1976-06-01 1977-09-13 Eastman Kodak Company Electrophoretic migration imaging process with neutral density bisazo pigments
US4299896A (en) * 1977-07-18 1981-11-10 Ricoh Co., Ltd. Electrophotographic sensitive materials containing a disazo pigment
US4841009A (en) * 1982-12-28 1989-06-20 Amoco Corporation Substantially linear monomeric composition and liquid crystal polymeric compositions derived therefrom
US5262330A (en) * 1992-02-27 1993-11-16 Miles Inc. Colorimetric methods and reagents for the assay of calcium in a test sample
US20060147652A1 (en) * 2004-12-31 2006-07-06 Industrial Technology Research Institute Dichroic dye and microencapsulated liquid crystal composition thereof
JP2006193742A (ja) * 2004-12-31 2006-07-27 Ind Technol Res Inst 二色性色素、その色素組成物、二色性色素を含むマイクロカプセル化液晶、液晶組成物および液晶表示デバイス
JP2010047775A (ja) * 2004-12-31 2010-03-04 Ind Technol Res Inst 二色性色素、その色素組成物、二色性色素を含むマイクロカプセル化液晶、液晶組成物および液晶表示デバイス

Also Published As

Publication number Publication date
GB1296863A (enrdf_load_stackoverflow) 1972-11-22
GB1296864A (enrdf_load_stackoverflow) 1972-11-22
DE1963197A1 (de) 1970-08-06
GB1296862A (enrdf_load_stackoverflow) 1972-11-22
FR2026846A1 (enrdf_load_stackoverflow) 1970-09-25

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