US3814752A - 6,6'-methylenebis(2-styryl benzopyrylium salt)as sensitizers for use in electrophotographic light-sensitive materials - Google Patents

6,6'-methylenebis(2-styryl benzopyrylium salt)as sensitizers for use in electrophotographic light-sensitive materials Download PDF

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Publication number
US3814752A
US3814752A US00259392A US25939272A US3814752A US 3814752 A US3814752 A US 3814752A US 00259392 A US00259392 A US 00259392A US 25939272 A US25939272 A US 25939272A US 3814752 A US3814752 A US 3814752A
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United States
Prior art keywords
methylenebis
solution
compound
sensitizers
perchlorate
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
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US00259392A
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English (en)
Inventor
M Ohta
T Kubota
M Harada
S Maruyama
K Kojima
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Ricoh Co Ltd
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Ricoh Co Ltd
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Publication date
Priority claimed from JP4473971A external-priority patent/JPS4926634B1/ja
Priority claimed from JP46050171A external-priority patent/JPS515786B1/ja
Application filed by Ricoh Co Ltd filed Critical Ricoh Co Ltd
Application granted granted Critical
Publication of US3814752A publication Critical patent/US3814752A/en
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • 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

Definitions

  • FIG. 6 o zra 3 4 0 7 s 9 :0 2025 z 9 R LUV) mm 0 l l l l l l l I l l V l l l l l l l A l Q 4000 3200 2400 I800 I600
  • sensitizers for use in an electrophotographic light-sensitive material containing an organic photoconductor.
  • the sensitizers comprise derivatives of 6,6-methylenebisbenzopyrylium salts.
  • the present invention relates to sensitizers for use in electrophotographic light-sensitive materials which contain organic photoconductors such as polyvinylcarbazole.
  • the sensitizers of the present invention are derivatives of 6,6-methylenebisbenzopyrylium salts having the following general formula:
  • Such derivatives of 6,6 methylenebisbenzopyrylium salts are used as sensitizers for an organic photoconductors such as polyvinylcarbazole or derivatives thereof. They are preferably used in an amount of 0.1 to 2.0% by weight based on the solid content, in a light-sensitive solution.
  • each light-sensitive product was allowed to stand in a dark place for several days, it was negatively charged by means of conventional corona discharge of 6 kv. and exposed to white light in contact with an image Original while illuminating the surface of the light-sensitive layer at 20 lux.
  • the wave length of absorption maximum was measured by reflection method for each of Compounds No. 1 to No. 15.
  • Electrophotographic light-sensitive materials were obtained following the same procedures as that of Examples 1-15 except that chlorinated polyvinylcarbazole was employed as a substitute for brominated polyvinylcarbazole.
  • the electrophotographic light-sensitive materials yielded an exact reproduction of original images in the same manner as that of Examples 1-15 except that the lightsensitive materials were exposed to light for 2 seconds while illuminating the surface of the light-sensitive layer at 20 lux.
  • the reaction temperature of the condensation and the cyclic condensation is preferably between 0 C. and 5 C.
  • reaction solution is poured into ether to crystallize.
  • reaction solution is poured into a cooled solution (concentration: 5-20%) containing acid or salt having a desired anion to crystallize.
  • This compound showed wave length of absorption maximum (A at 576 111,11. and molecular extinction coefficient (e) of 1016x10 in dichloroethane.
  • This compound showed wave length of absorption maximum (A at 559 my and molecular extinction coefiicient (e) of 8.79X10 in dichloroethane.
  • benzopyrylium salts having C10 as an anion have been shown.
  • Benzopyrylium salts having BF;- or AuCl; as an anion can be obtained by using an aqueous solution of sodium tetrafluoroborate (NaBF or chloroauric acid (HAuCl instead of an aqueous solution of perchloric acid (H010).
  • a sensitizer for use in an electrophotographic lightsensitive material having the formula (I):
  • a rivative isj- 6;6' methvlenebisn (4Gmethoxynaphthyii '4.
  • a sensitize: afbording'tofclaim'lfwheiiein rivativ'e" is 6,6 "'methy1enebis'[2 (p"-methoxystyryl)-3'- decylbenzopyryliumperchlorate a 5.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
US00259392A 1971-06-21 1972-06-05 6,6'-methylenebis(2-styryl benzopyrylium salt)as sensitizers for use in electrophotographic light-sensitive materials Expired - Lifetime US3814752A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP4473971A JPS4926634B1 (de) 1971-06-21 1971-06-21
JP46050171A JPS515786B1 (de) 1971-07-07 1971-07-07

Publications (1)

Publication Number Publication Date
US3814752A true US3814752A (en) 1974-06-04

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US00259392A Expired - Lifetime US3814752A (en) 1971-06-21 1972-06-05 6,6'-methylenebis(2-styryl benzopyrylium salt)as sensitizers for use in electrophotographic light-sensitive materials

Country Status (4)

Country Link
US (1) US3814752A (de)
DE (1) DE2230302C3 (de)
FR (1) FR2143195B1 (de)
GB (1) GB1390429A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9663477B1 (en) 2014-09-19 2017-05-30 The United States Of America As Represented By The Secretary Of The Navy Synthesis and structure of 3,5-diamino-2,6-di-(tert-butyl-NNO-azoxy) pyrazine as a critical intermediate in the synthesis of a novel energetic compound

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9663477B1 (en) 2014-09-19 2017-05-30 The United States Of America As Represented By The Secretary Of The Navy Synthesis and structure of 3,5-diamino-2,6-di-(tert-butyl-NNO-azoxy) pyrazine as a critical intermediate in the synthesis of a novel energetic compound

Also Published As

Publication number Publication date
FR2143195B1 (de) 1973-07-13
DE2230302A1 (de) 1972-12-28
GB1390429A (en) 1975-04-09
DE2230302B2 (de) 1974-09-05
DE2230302C3 (de) 1975-05-15
FR2143195A1 (de) 1973-02-02

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