US4251614A
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Novel disazo compounds, process for the preparation of same and application of said disazo compounds and analogues thereof to electrophotographic sensitive materials
Assignee: Ricoh Co Ltd
•
Filing: 1978-06-30
•
Granted: 1981-02-17
•
Expires: 1998-06-30
Abstract
Abstract The present invention provides disazo compounds expressed by the general formula: ##STR1## [wherein A represents a member selected from the group consisting of ##STR2## (wherein X represents a member selected from the group consisting of aromatic rings such as benzene ring, naphthalene ring, etc., hetero rings such as indole ring, carbazole ring, benzofuran ring, etc. and their substituents, Ar 1 represents a member selected from the group consisting of aromatic rings such as benzene ring, naphthalene ring, etc., hetero rings such as dibenzofuran ring, etc. and their substituents, Ar 2 and Ar 3 represent a member selected from the group consisting of aromatic rings such as benzene ring, naphthalene ring, etc. and their substituents, R 1 and R 3 represent a member selected from the group consisting of hydrogen, lower alkyl radical or phenyl radical and their substituents and R 2 represents a member selected from the group consisting of lower alkyl radical, carboxyl radical and their esters)]; 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 said disazo compound as an effective ingredient.
Inventors
- 👤 Masaomi Sasaki
- 👤 Kiyoshi Sakai
- 👤 Mitsuru Hashimoto
- 👤 Masafumi Ohta
- 👤 Kyoji Tsutsui
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 07:02
CPC Classifications
C; C09; C09B; C09B35/00; C09B35/02; C09B35/039; C09B35/34; G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0664; G03G5/0675; G03G5/0679; G03G5/0683; G03G5/0685
Claims Analysis
Total Claims: 72
Claim 1
Independent Claim
202 words
An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of a disazo pigment having a particle size of 5 microns or less, said disazo pigment having the formula ##STR43## wherein A is a member selected from the group consisting of ##STR44## wherein the molecular fragment ##STR45## is a fused polycyclic ring system in which the segment ##STR46## is 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
202 words
An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of a disazo pigment having a particle size of 5 microns or less, said disazo pigment having the formula ##STR43## wherein A is a member selected from the group consisting of ##STR44## wherein the molecular fragment ##STR45## is a fused polycyclic ring system in which the segment ##STR46## is 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
12 words
An electrophotographic material according to claim 1 in which A is ##STR47##
Claim 4
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR48##
Claim 5
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR49##
Claim 6
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR50##
Claim 7
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR51##
Claim 8
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR52##
Claim 9
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR53##
Claim 10
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR54##
Claim 11
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR55##
Claim 12
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR56##
Claim 13
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR57##
Claim 14
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR58##
Claim 15
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR59##
Claim 16
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR60##
Claim 17
Dependent Claim
12 words
An electrophotographic material according to claim 1 in which A is ##STR61##
Claim 18
Dependent Claim
44 words
An electrophotographic material according to claim 1, wherein the content of said disazo pigment 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 19
Dependent Claim
205 words
An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of a disazo pigment having a particle size of 5 microns or less, said disazo pigment having the formula ##STR62## wherein A is a member selected from the group consisting of ##STR63## wherein the molecular fragment ##STR64## is a fused polycyclic ring system in which the segment ##STR65## is 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 charge-transfer substance and a resinous binder.
Claim 20
Dependent Claim
205 words
An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of a disazo pigment having a particle size of 5 microns or less, said disazo pigment having the formula ##STR62## wherein A is a member selected from the group consisting of ##STR63## wherein the molecular fragment ##STR64## is a fused polycyclic ring system in which the segment ##STR65## is 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 charge-transfer substance and a resinous binder.
Claim 21
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR66##
Claim 22
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR67##
Claim 23
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR68##
Claim 24
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR69##
Claim 25
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR70##
Claim 26
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR71##
Claim 27
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR72##
Claim 28
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR73##
Claim 29
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR74##
Claim 30
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR75##
Claim 31
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR76##
Claim 32
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR77##
Claim 33
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR78##
Claim 34
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR79##
Claim 35
Dependent Claim
12 words
An electrophotographic material according to claim 18 in which A is ##STR80##
Claim 36
Dependent Claim
68 words
An electrophotographic material according to claim 18, wherein the content of said disazo pigment is in the range of from 1 to 50% based on the weight of the photosensitive layer, and 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 37
Dependent Claim
222 words
An electrophotographic material which comprises an electrically conductive support and a charge-carrier generating layer formed thereon, said charge-carrier generating layer consisting essentially of a disazo compound having a particle size of 5 microns or less, said disazo pigment having the formula ##STR81## wherein A is a member selected from the group consisting of ##STR82## wherein the molecular fragment ##STR83## is a fused polycyclic ring system in which the segment ##STR84## is 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 38
Dependent Claim
222 words
An electrophotographic material which comprises an electrically conductive support and a charge-carrier generating layer formed thereon, said charge-carrier generating layer consisting essentially of a disazo compound having a particle size of 5 microns or less, said disazo pigment having the formula ##STR81## wherein A is a member selected from the group consisting of ##STR82## wherein the molecular fragment ##STR83## is a fused polycyclic ring system in which the segment ##STR84## is 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 39
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR85##
Claim 40
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR86##
Claim 41
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR87##
Claim 42
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR88##
Claim 43
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR89##
Claim 44
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR90##
Claim 45
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR91##
Claim 46
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR92##
Claim 47
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR93##
Claim 48
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR94##
Claim 49
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR95##
Claim 50
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR96##
Claim 51
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR97##
Claim 52
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR98##
Claim 53
Dependent Claim
12 words
An electrophotographic material according to claim 35 in which A is ##STR99##
Claim 54
Dependent Claim
56 words
An electrophotographic material according to claim 35, wherein the content of said charge-transfer substance is in the range of from 10 to 95% based on the weight of said charge-transfer layer, the thickness of said charge-carrier generating layer is 5 microns or less and the thickness of said charge-transfer layer is about 3 to 50 microns.
Claim 55
Dependent Claim
221 words
An electrophotographic material which comprises an electrically conductive support, a charge-transfer layer on said support, said charge-transfer layer consisting essentially of a charge-transfer substance and a resinous binder, and a charge-carrier generating layer on said charge-transfer layer, said charge-carrier generating layer consisting essentially of a disazo compound having a particle size of 5 microns or less, said disazo pigment having the formula ##STR100## wherein A is a member selected from the group consisting of ##STR101## wherein the molecular fragment ##STR102## is a fused polycyclic ring system in which the segment ##STR103## is 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 .
Claim 56
Dependent Claim
221 words
An electrophotographic material which comprises an electrically conductive support, a charge-transfer layer on said support, said charge-transfer layer consisting essentially of a charge-transfer substance and a resinous binder, and a charge-carrier generating layer on said charge-transfer layer, said charge-carrier generating layer consisting essentially of a disazo compound having a particle size of 5 microns or less, said disazo pigment having the formula ##STR100## wherein A is a member selected from the group consisting of ##STR101## wherein the molecular fragment ##STR102## is a fused polycyclic ring system in which the segment ##STR103## is 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 .
Claim 57
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR104##
Claim 58
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR105##
Claim 59
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR106##
Claim 60
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR107##
Claim 61
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR108##
Claim 62
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR109##
Claim 63
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR110##
Claim 64
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR111##
Claim 65
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR112##
Claim 66
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR113##
Claim 67
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR114##
Claim 68
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR115##
Claim 69
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR116##
Claim 70
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR117##
Claim 71
Dependent Claim
12 words
An electrophotographic material according to claim 52 in which A is ##STR118##
Claim 72
Dependent Claim
56 words
An electrophotographic material according to claim 52, wherein the content of said charge-transfer substance is in the range of from 10 to 95% based on the weight of said charge-transfer layer, the thickness of said charge-carrier generating layer is 5 microns or less and the thickness of said charge-transfer layer is about 3 to 50 microns.
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