US3730711A - Photoconductive material for electrophotography - Google Patents

Photoconductive material for electrophotography Download PDF

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Publication number
US3730711A
US3730711A US00063619A US3730711DA US3730711A US 3730711 A US3730711 A US 3730711A US 00063619 A US00063619 A US 00063619A US 3730711D A US3730711D A US 3730711DA US 3730711 A US3730711 A US 3730711A
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US
United States
Prior art keywords
group
lower alkyl
film
electrophotography
sensitive layer
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
Application number
US00063619A
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English (en)
Inventor
H Ono
S Watarai
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.)
Fujifilm Holdings Corp
Original Assignee
Fuji Photo Film Co Ltd
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 Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd
Application granted granted Critical
Publication of US3730711A publication Critical patent/US3730711A/en
Anticipated expiration legal-status Critical
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Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622Heterocyclic compounds
    • G03G5/0624Heterocyclic compounds containing one hetero ring
    • G03G5/0627Heterocyclic compounds containing one hetero ring being five-membered
    • G03G5/0629Heterocyclic compounds containing one hetero ring being five-membered containing one hetero atom
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622Heterocyclic compounds
    • G03G5/0644Heterocyclic compounds containing two or more hetero rings
    • G03G5/0661Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring

Definitions

  • R represents a hydrogen, a halogen atom, a lower alkyl --NO --OR or COOR group (R being a lower alkyl group); R represents H, OR CN or a phenyl group (R being H or a lower alkyl group); n is an integer having the value of l-4; X represents either a single bond or NH- group.
  • R is a hydrogen, a halogen atom, a lower alkyl, -NO OR or COOR group (R being a lower alkyl group): R is H, --R CN or a phenyl group (R being H or a lower alkyl group): n is an'integer having" the value of 1-4; X is either a single bond or -NH.
  • R, R R R n and X have the meanings given in general Formula I, R, is an alkyl, an alkenyl, an aryl, or an aralkyl group; and R is a divalent linking radical like:
  • the lower alkyl group represents an alkyl group having 1-4 carbon atoms.
  • the foregoing compounds have new structures entirely different from those of the conventionally known organic photoconductive materials for use in electrophotography.
  • those in which X is -NH-- are synthesized by the reaction Z-methylene indoline derivatives with isocyanates (refer to 0, Mumm, Ber 72 2107 (1939)) and further those in which X is a single bond are synthesized by the reaction of 2-methylene indoline derivatives with chlorides of acids (refer to Piccinini; Gazg, chim, ital, 28 (i), 187 (1898)).
  • resinous film forming binders usable in this case, there may be cited styrene-butadiene copolymer, polystyrene, chlorinated rubber, polyvinyl chloride, vinyl chloride/vinyl acetate copolymer, polyvinylidene chloride, nitrocellulose, polyvinyl acetate, polyvinyl acetal, polyvinyl ether, silicone resin, methacrylic resin, acrylic resin, phenol resin, alkyd resin, urea/ aldehyde. resin, etc.
  • the plasticizers usable include chlorinated biphenyl, chlorinated paraffin, phosphate type plasticizers, and phthalate type plasticizers.
  • sensitizers those which are known commonly are useful, including tetracyanoethylene, tetracyanodimethane, chloranil, naphthoquinone, anthraquinone, methylene blue, crystal violet, malachite green, etc.
  • the sensitive layer is deposited to a, dry thickness of 2-20,u. on the electroconductive base.
  • the organic photoconductive component accounts for more than-% by weight all of the film composition, theproduct is found to exhibit satisfactory properties from the electrophotographic point of view.
  • EXAMPLE 1 One-half (0.5) g. of Compound No. 1 given in Table 1 and 20 cc. of 10% benzene solution of polystyrene were mixed homogeneously. The resultants solution was spread to a dry film thickness of 5p. on a base of aluminum plate to obtain a sensitive layer. After drying of the solvent, the sensitive layer was positively charged in a dark place. With a film containing a positive image placed thereon, the sensitive layer was exposed through the film to a highvoltage mercury bulb (made by Toshiba, SHL-lOO) placed at a distance of 30 cm. above for about '8 seconds.
  • a highvoltage mercury bulb made by Toshiba, SHL-lOO
  • EXAMPLE 5 styrene; The final-solution 'was spread to a dry film thickness of 5 1. on an aluminum plate to form a sensitive layer. After drying of the solvent, the said sensitive layer was charged positively in a dark place. With a positive image film placed on top thereof, the sensitive layer was exposed through the film to a high-voltage mercury bulb placed at a distance of 30 cm. above for a second. Through the steps of developing and fixing, there was obtained a clear positive image.
  • R is a hydrogen, a halogen atom, a lower alkyl, -N0 -OR or -COOR group (R being a lower alkyl group); R is H, -OR -CN or a phenyl group (R being H or a lower alkyl group); n is an integer having the value of 1-4; X is either a single bond or -NH--; R is an alkyl, an alkenyl, an aryl, or an aralkyl group;
  • R is a divalent linking radical selected from the 6.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Indole Compounds (AREA)
US00063619A 1969-08-13 1970-08-13 Photoconductive material for electrophotography Expired - Lifetime US3730711A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP44064037A JPS4832381B1 (enrdf_load_stackoverflow) 1969-08-13 1969-08-13

Publications (1)

Publication Number Publication Date
US3730711A true US3730711A (en) 1973-05-01

Family

ID=13246502

Family Applications (1)

Application Number Title Priority Date Filing Date
US00063619A Expired - Lifetime US3730711A (en) 1969-08-13 1970-08-13 Photoconductive material for electrophotography

Country Status (7)

Country Link
US (1) US3730711A (enrdf_load_stackoverflow)
JP (1) JPS4832381B1 (enrdf_load_stackoverflow)
BE (1) BE754699A (enrdf_load_stackoverflow)
CA (1) CA925087A (enrdf_load_stackoverflow)
DE (1) DE2040152B2 (enrdf_load_stackoverflow)
FR (1) FR2056709A5 (enrdf_load_stackoverflow)
GB (1) GB1272720A (enrdf_load_stackoverflow)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3798031A (en) * 1971-11-10 1974-03-19 Agfa Gevaert Nv Photoconductive 1,2,3,4-tetrahydroquinolines employed in electrophotography
US3852208A (en) * 1968-12-30 1974-12-03 Canon Kk Photoconductive toner composition
US3874943A (en) * 1972-05-31 1975-04-01 Fuji Photo Film Co Ltd Sensitizers for electrophotography
US3930851A (en) * 1971-10-06 1976-01-06 Fuji Photo Film Co., Ltd. Electrophotographic process using methylene indoline photoconductive derivatives
US3933664A (en) * 1968-12-30 1976-01-20 Canon Inc. Organic photoconductive toner materials
US4465753A (en) * 1982-07-08 1984-08-14 Dainippon Ink And Chemicals Inc. Indoline electrophotoconductor
US20110105362A1 (en) * 2003-08-11 2011-05-05 Life Technologies Corporation Cyanine compounds and their application as quenching compounds

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5299185U (enrdf_load_stackoverflow) * 1976-01-23 1977-07-26
JPS5368787U (enrdf_load_stackoverflow) * 1976-11-11 1978-06-09
JPS5594799U (enrdf_load_stackoverflow) * 1979-12-20 1980-07-01
JPS6017693U (ja) * 1983-07-15 1985-02-06 安藤 通男 円孔付き巻たばこ火消し器

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3852208A (en) * 1968-12-30 1974-12-03 Canon Kk Photoconductive toner composition
US3933664A (en) * 1968-12-30 1976-01-20 Canon Inc. Organic photoconductive toner materials
US3930851A (en) * 1971-10-06 1976-01-06 Fuji Photo Film Co., Ltd. Electrophotographic process using methylene indoline photoconductive derivatives
US3798031A (en) * 1971-11-10 1974-03-19 Agfa Gevaert Nv Photoconductive 1,2,3,4-tetrahydroquinolines employed in electrophotography
US3874943A (en) * 1972-05-31 1975-04-01 Fuji Photo Film Co Ltd Sensitizers for electrophotography
US4465753A (en) * 1982-07-08 1984-08-14 Dainippon Ink And Chemicals Inc. Indoline electrophotoconductor
US20110105362A1 (en) * 2003-08-11 2011-05-05 Life Technologies Corporation Cyanine compounds and their application as quenching compounds
US9150922B2 (en) 2003-08-11 2015-10-06 Life Technologies Corporation Cyanine compounds and their application as quenching compounds

Also Published As

Publication number Publication date
FR2056709A5 (enrdf_load_stackoverflow) 1971-05-14
CA925087A (en) 1973-04-24
DE2040152A1 (de) 1971-03-11
DE2040152B2 (de) 1974-03-28
DE2040152C3 (enrdf_load_stackoverflow) 1974-10-31
JPS4832381B1 (enrdf_load_stackoverflow) 1973-10-05
BE754699A (fr) 1971-01-18
GB1272720A (en) 1972-05-03

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