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US4272598A Expired / Lapsed US ⏱️ 0.0 years remaining

Electrophotographic material containing disazo compounds

Assignee: Ricoh Co Ltd
•
Filing: 1978-04-20
•
Granted: 1981-06-09
•
Expires: 1998-04-20
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Abstract

Abstract The present invention provides disazo compounds expressed by the general formula I ##STR1## [wherein A represents ##STR2## (wherein R represents alkyl radical, alkoxy radical, nitro radical, dialkylamino radical or halogen, n is 0 or an integer of 1, 2 or 3, and R may be either identical or different when n is an integer of 2 or 3)]; a process for the preparation of said compounds; and electrophotographic sensitive materials having a high sensitivity as well as a high flexibility which comprise a conductive support and a photosensitive layer formed thereon, said photosensitive layer containing a disazo compound, as an effective ingredient, which is expressed by the general formula II ##STR3## [wherein A' represents ##STR4## (wherein X represents aromatic rings such as benzene ring, naphthalene ring, etc., hetero rings such as indole ring, carbazole ring, benzofuran ring, etc. or their substituents, Ar 1 represents aromatic rings such as benzene ring, naphthalene ring, etc., hetero rings such as dibenzofuran, etc. or their substituents, Ar 2 and Ar 3 represent aromatic rings such as benzene ring, naphthalene ring, etc. or their substituents, R 1 and R 3 represent respectively hydrogen, lower alkyl radical, phenyl radical or their substituents, and R 2 represents lower alkyl radical, carboxyl radical or their esters)].

Inventors

  • 👤 Masaomi Sasaki
  • 👤 Kiyoshi Sakai
  • 👤 Mitsuru Hashimoto
  • 👤 Masafumi Ohta
  • 👤 Akio Kozima

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 17:21
CPC Classifications
G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0664; G03G5/0675; G03G5/0679; G03G5/0683; C; C09; C09B; C09B35/00; C09B35/02; C09B35/039; C09B35/205; C09B35/215; C09B56/00; C09B56/04; C09B56/06

Claims Analysis

Total Claims: 57
Claim 1
Independent Claim 180 words
An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of fine particles of a disazo compound having the formula ##STR48## wherein A' is a member selected from the group consisting of ##STR49## is a fused ring selected from the group consisting of benzene ring, halobenzene ring, naphthalene ring, indole ring, carbazole ring and benzofuran ring; Ar 1 is a member selected from the group consisting of phenyl, methylphenyl, methoxyphenyl, chlorophenyl, nitrophenyl, ethoxyphenyl, methylchlorophenyl, dimethylphenyl, methoxychlorophenyl, methoxybromophenyl, methoxymethylphenyl, dimethoxyphenyl, dimethoxychlorophenyl, dimethylaminophenyl, cyanophenyl, carboxyphenyl, benzenesulfonic acid sodium salt, tert-butoxyphenyl, naphthyl, methoxydibenzofuryl and carbazolyl; each of Ar 2 and Ar 3 is a member selected from the group consisting of phenyl, naphthyl, methoxyphenyl, methylphenyl, acetylaminophenyl, dimethylaminophenyl, cyanophenyl, nitrophenyl, dinitrophenyl, chlorophenyl, trichlorobenzenesulfonic acid, benzenesulfonic acid and benzenesulfonamide; each of R 1 and R 3 is a member selected from the group consisting of hydrogen, methyl, ethyl, phenyl and chlorophenyl; and R 2 is a member selected from the group consisting of methyl, carboxyl and --COOC 2 H 5 ; and a resinous binder.
Claim 2
Dependent Claim 180 words
An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of fine particles of a disazo compound having the formula ##STR48## wherein A' is a member selected from the group consisting of ##STR49## is a fused ring selected from the group consisting of benzene ring, halobenzene ring, naphthalene ring, indole ring, carbazole ring and benzofuran ring; Ar 1 is a member selected from the group consisting of phenyl, methylphenyl, methoxyphenyl, chlorophenyl, nitrophenyl, ethoxyphenyl, methylchlorophenyl, dimethylphenyl, methoxychlorophenyl, methoxybromophenyl, methoxymethylphenyl, dimethoxyphenyl, dimethoxychlorophenyl, dimethylaminophenyl, cyanophenyl, carboxyphenyl, benzenesulfonic acid sodium salt, tert-butoxyphenyl, naphthyl, methoxydibenzofuryl and carbazolyl; each of Ar 2 and Ar 3 is a member selected from the group consisting of phenyl, naphthyl, methoxyphenyl, methylphenyl, acetylaminophenyl, dimethylaminophenyl, cyanophenyl, nitrophenyl, dinitrophenyl, chlorophenyl, trichlorobenzenesulfonic acid, benzenesulfonic acid and benzenesulfonamide; each of R 1 and R 3 is a member selected from the group consisting of hydrogen, methyl, ethyl, phenyl and chlorophenyl; and R 2 is a member selected from the group consisting of methyl, carboxyl and --COOC 2 H 5 ; and a resinous binder.
Claim 3
Dependent Claim 56 words
An electrophotographic material according to claim 1, wherein the particle size of said disazo compound is less than 5 microns, the content of said disazo compound is in the range of from 30 to 70% based on the weight of the photosensitive layer and the thickness of said photosensitive layer is about 3 to 50 microns.
Claim 4
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR50##
Claim 5
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR51##
Claim 6
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR52##
Claim 7
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR53##
Claim 8
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR54##
Claim 9
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR55##
Claim 10
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR56##
Claim 11
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR57##
Claim 12
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR58##
Claim 13
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR59##
Claim 14
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR60##
Claim 15
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR61##
Claim 16
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR62##
Claim 17
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR63##
Claim 18
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR64##
Claim 19
Dependent Claim 12 words
An electrophotographic material according to claim 1 in which A' is ##STR65##
Claim 20
Dependent Claim 183 words
An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of fine particles of a disazo compound having the formula ##STR66## wherein A' is a member selected from the group consisting of ##STR67## is a fused ring selected from the group consisting of benzene ring, halobenzene ring, naphthalene ring, indole ring, carbazole ring and benzofuran ring; Ar 1 is a member selected from the group consisting of phenyl, methylphenyl, methoxyphenyl, chlorophenyl, nitrophenyl, ethoxyphenyl, methylchlorophenyl, dimethylphenyl, methoxychlorophenyl, methoxybromophenyl, methoxymethylphenyl, dimethoxyphenyl, dimethoxychlorophenyl, dimethylaminophenyl, cyanophenyl, carboxyphenyl, benzenesulfonic acid sodium salt, tert-butoxyphenyl, naphthyl, methoxydibenzofuryl and carbazolyl; each of Ar 2 and Ar 3 is a member selected from the group consisting of phenyl, naphthyl, methoxyphenyl, methylphenyl, acetylaminophenyl, dimethylaminophenyl, cyanophenyl, nitrophenyl, dinitrophenyl, chlorophenyl, trichlorobenzenesulfonic acid, benzenesulfonic acid and benzenesulfonamide; each of R 1 and R 3 is a member selected from the group consisting of hydrogen, methyl, ethyl, phenyl and chlorophenyl; and R 2 is a member selected from the group consisting of methyl, carboxyl and --COOC 2 H 5 ; a chargetransfer substance and a resinous binder.
Claim 21
Dependent Claim 183 words
An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of fine particles of a disazo compound having the formula ##STR66## wherein A' is a member selected from the group consisting of ##STR67## is a fused ring selected from the group consisting of benzene ring, halobenzene ring, naphthalene ring, indole ring, carbazole ring and benzofuran ring; Ar 1 is a member selected from the group consisting of phenyl, methylphenyl, methoxyphenyl, chlorophenyl, nitrophenyl, ethoxyphenyl, methylchlorophenyl, dimethylphenyl, methoxychlorophenyl, methoxybromophenyl, methoxymethylphenyl, dimethoxyphenyl, dimethoxychlorophenyl, dimethylaminophenyl, cyanophenyl, carboxyphenyl, benzenesulfonic acid sodium salt, tert-butoxyphenyl, naphthyl, methoxydibenzofuryl and carbazolyl; each of Ar 2 and Ar 3 is a member selected from the group consisting of phenyl, naphthyl, methoxyphenyl, methylphenyl, acetylaminophenyl, dimethylaminophenyl, cyanophenyl, nitrophenyl, dinitrophenyl, chlorophenyl, trichlorobenzenesulfonic acid, benzenesulfonic acid and benzenesulfonamide; each of R 1 and R 3 is a member selected from the group consisting of hydrogen, methyl, ethyl, phenyl and chlorophenyl; and R 2 is a member selected from the group consisting of methyl, carboxyl and --COOC 2 H 5 ; a chargetransfer substance and a resinous binder.
Claim 22
Dependent Claim 79 words
An electrophotographic material according to claim 19, wherein the particle size of said disazo compound is less than 5 microns, the content of said disazo compound is in the range of from 1 to 50% based on the weight of the photosensitive layer, the content of said charge-transfer substance is in the range of from 10 to 95% based on the weight of the photosensitive layer, and the thickness of said photosensitive layer is about 3 to 50 microns.
Claim 23
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR68##
Claim 24
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR69##
Claim 25
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR70##
Claim 26
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR71##
Claim 27
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR72##
Claim 28
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR73##
Claim 29
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR74##
Claim 30
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR75##
Claim 31
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR76##
Claim 32
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR77##
Claim 33
Dependent Claim 11 words
An electrophotographic material to claim 19 in which A' is ##STR78##
Claim 34
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR79##
Claim 35
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR80##
Claim 36
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR81##
Claim 37
Dependent Claim 12 words
An electrophotographic material according to claim 19 in which A' is ##STR82##
Claim 38
Dependent Claim 11 words
An electrophotographic material according to claim 19 in which A'is ##STR83##
Claim 39
Dependent Claim 197 words
An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of fine particles of a disazo compound having the formula ##STR84## wherein A' is a member selected from the group consisting of ##STR85## is a fused ring selected from the group consisting of benzene ring, halobenzene ring, naphthalene ring, indole ring, carbazole ring and benzofuran ring; Ar 1 is a member selected from the group consisting of phenyl, methylphenyl, methoxyphenyl, chlorophenyl, nitrophenyl, ethoxyphenyl, methylchlorophenyl, dimethylphenyl, methoxychlorophenyl, methoxybromophenyl, methoxymethylphenyl, dimethoxyphenyl, dimethoxychlorophenyl, dimethylaminophenyl, cyanophenyl, carboxyphenyl, benzenesulfonic acid sodium salt, tert-butoxyphenyl, naphthyl, methoxydibenzofuryl and carbazolyl; each of Ar 2 and Ar 3 is a member selected from the group consisting of phenyl, naphthyl, methoxyphenyl, methylphenyl, acetylaminophenyl, dimethylaminophenyl, cyanophenyl, nitrophenyl, dinitrophenyl, chlorophenyl, trichlorobenzenesulfonic acid, benzenesulfonic acid and benzenesulfonamide; each of R 1 and R 3 is a member selected from the group consisting of hydrogen, methyl, ethyl, phenyl and chlorophenyl; and R 2 is a member selected from the group consisting of methyl, carboxyl and --COOC 2 H 5 ; and a charge-transfer layer on said charge-carrier-generating layer, said charge-transfer layer consisting essentially of a charge-transfer substance and a resinous binder.
Claim 40
Dependent Claim 197 words
An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of fine particles of a disazo compound having the formula ##STR84## wherein A' is a member selected from the group consisting of ##STR85## is a fused ring selected from the group consisting of benzene ring, halobenzene ring, naphthalene ring, indole ring, carbazole ring and benzofuran ring; Ar 1 is a member selected from the group consisting of phenyl, methylphenyl, methoxyphenyl, chlorophenyl, nitrophenyl, ethoxyphenyl, methylchlorophenyl, dimethylphenyl, methoxychlorophenyl, methoxybromophenyl, methoxymethylphenyl, dimethoxyphenyl, dimethoxychlorophenyl, dimethylaminophenyl, cyanophenyl, carboxyphenyl, benzenesulfonic acid sodium salt, tert-butoxyphenyl, naphthyl, methoxydibenzofuryl and carbazolyl; each of Ar 2 and Ar 3 is a member selected from the group consisting of phenyl, naphthyl, methoxyphenyl, methylphenyl, acetylaminophenyl, dimethylaminophenyl, cyanophenyl, nitrophenyl, dinitrophenyl, chlorophenyl, trichlorobenzenesulfonic acid, benzenesulfonic acid and benzenesulfonamide; each of R 1 and R 3 is a member selected from the group consisting of hydrogen, methyl, ethyl, phenyl and chlorophenyl; and R 2 is a member selected from the group consisting of methyl, carboxyl and --COOC 2 H 5 ; and a charge-transfer layer on said charge-carrier-generating layer, said charge-transfer layer consisting essentially of a charge-transfer substance and a resinous binder.
Claim 41
Dependent Claim 67 words
An electrophotographic layer according to claim 37, wherein the particle size of said disazo compound is less than 5 microns, the content of said charge-transfer substance is in the range of from 10 to 95% based on the weight of the charge-transfer layer, the thickness of said photosensitive layer is less than 5 microns and the thickness of said charge-transfer layer is about 3 to 50 microns.
Claim 42
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR86##
Claim 43
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR87##
Claim 44
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR88##
Claim 45
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR89##
Claim 46
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR90##
Claim 47
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR91##
Claim 48
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR92##
Claim 49
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR93##
Claim 50
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR94##
Claim 51
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR95##
Claim 52
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR96##
Claim 53
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR97##
Claim 54
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR98##
Claim 55
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR99##
Claim 56
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR100##
Claim 57
Dependent Claim 12 words
An electrophotographic material according to claim 37 in which A' is ##STR101##

References Cited (Backward Citations)

US4026704A Cited
US4018607A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-06-08 1984-12-08 1985-06-09 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-06-08 1988-12-08 1989-06-09 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-06-08 1992-12-08 1993-06-09 $7700.00 Window Closed / Lapsed

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