US4446217A
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Electrophotographic photosensitive member having a hydrazone containing layer
Assignee: Canon Inc
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Filing: 1982-01-27
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Granted: 1984-05-01
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Expires: 2002-01-27
Abstract
Abstract An electrophotographic photosensitive member comprises a layer containing a hydrazone compound represented by the following formula (1) or (2): ##STR1## wherein, Z is an atomic group necessary to complete a substituted or unsubstituted heterocyclic ring; R 11 , R 12 , R 21 , R 22 and R 23 represent substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl, and the combinations of R 11 with R 12 and of R 22 with R 23 can form each a pyrrolidine ring, piperidine ring, or morpholine ring; n is 1 or 2; and A is a monovalent heterocyclic compound residue.
Inventors
- 👤 Yoshio Takasu
- 👤 Shozo Ishikawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 21:02
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/02; C07D263/08; C07D263/10; C07D209/00; C07D209/56; C07D209/80; C07D209/82; C07D209/86; C07D263/52; C07D263/54; C07D263/56; C07D271/00; C07D271/02; C07D271/10; C07D277/00; C07D277/02; C07D277/08; C07D277/10; C07D277/60; C07D277/62; C07D277/64; C07D277/84; G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0601; G03G5/0612; G03G5/0616; G03G5/0622; G03G5/0624; G03G5/0627; G03G5/0635; G03G5/0644; G03G5/0661
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
126 words
An electrophotographic photosensitive member comprisng a layer containing a hydrazone compound represented by the following formula ( 1) or (2): ##STR22## wherein, Z is an atomic group necessary to complete a substituted or unsubstituted heterocyclic ring; selected from the group consisting of thiazoline, oxazoline, imidazoline, thiazole, oxazole, imidazole, benzothiazole, benzoxazole, benzimidazole, naphthothiazole, naphthoxazole, naphthoimidazole, quinoline, isoquinoline, quinoxaline, pyridazine, pyrimidine, pyrazine, triazole, oxadiazole, and thiadiazole; R 21 , R 22 and R 23 represent substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl, and the combinations of R 11 with R 12 and of R 22 with R 23 can form each a pyrrolidine ring, piperidine ring, or morpholine ring; n is 1 or 2, and A is a monovalent heterocyclic ring residue.
Claim 2
Dependent Claim
126 words
An electrophotographic photosensitive member comprisng a layer containing a hydrazone compound represented by the following formula ( 1) or (2): ##STR22## wherein, Z is an atomic group necessary to complete a substituted or unsubstituted heterocyclic ring; selected from the group consisting of thiazoline, oxazoline, imidazoline, thiazole, oxazole, imidazole, benzothiazole, benzoxazole, benzimidazole, naphthothiazole, naphthoxazole, naphthoimidazole, quinoline, isoquinoline, quinoxaline, pyridazine, pyrimidine, pyrazine, triazole, oxadiazole, and thiadiazole; R 21 , R 22 and R 23 represent substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl, and the combinations of R 11 with R 12 and of R 22 with R 23 can form each a pyrrolidine ring, piperidine ring, or morpholine ring; n is 1 or 2, and A is a monovalent heterocyclic ring residue.
Claim 3
Dependent Claim
59 words
An electrophotographic photosensitive member of claim 1, wherein said hydrazone compound is represented by formula (1) of which Z, when n is 1, is an atomic group necessary to complete a substituted or unsubstituted heterocyclic ring of thiazoline, oxazoline, imidazoline, thiazole, oxazole, imidazole, benzothiazole, benzoxazole, benzimidazole, naphthothiazole, naphthoxazole, naphthimidazole, 2-quinoline, isoquinoline, quinoxaline, pyridazine, pyrimidine, pyrazine, triazole, oxadiazole, or thiadiazole.
Claim 4
Dependent Claim
44 words
An electrophotographic photosensitive member of claim 2, wherein said hydrazone compound is represented by formula (1) of which Z, when n is 1, is an atomic group necessary to complete a substituted or unsubstituted heterocyclic ring of thiazole, benzothiazole, naphthothiazole, oxazole, benzoxazole, or naphthoxazole.
Claim 5
Dependent Claim
40 words
An electrophotographic photosensitive member of claim 3, wherein said hydrazone compound is represented by formula (1) of which Z, when n is 1, is an atomic group necessary to complete a substituted or unsubstituted heterocyclic ring of thiazole or benzothiazole.
Claim 6
Dependent Claim
33 words
An electrophotographic photosensitive member of claim 1, wherein said hydrazone compound is represented by formula (1) where at least one of R 11 and R 12 is phenyl, toryl, alkoxyphenyl, α-naphthyl, or β-naphthyl.
Claim 7
Dependent Claim
30 words
An electrophotographic photosensitive member of claim 5, wherein said hydrazone compound is represented by formula (1) where R 12 is methyl, ethyl, 2-hydroxyethyl, phenyl, tolyl, alkoxyphenyl, benzyl, α-naphthyl, or β-naphthyl.
Claim 8
Dependent Claim
47 words
An electrophotographic photosensitive member of claim 1, wherein said hydrazone compound is represented by formula (2) of which A is a monovalent residue of substituted or unsubstituted heterocyclic ring of pyrrole, pyrazole, pyrimidine, pyridazine, pyridine, indole, benzimidazole, carbazole, furan, oxazole, benzoxazole, benzofuran, dibenzofuran, thiophene, thiazole, or benzothiazole.
Claim 9
Dependent Claim
34 words
An electrophotographic photosensitive member of claim 7, wherein said hydrazone compound is represented by formula (2) of which A is a monovalent residue of substituted or unsubstituted heterocyclic ring of carbazole, thiazole, or benzothiazole.
Claim 10
Dependent Claim
27 words
An electrophotographic photosensitive member of claim 1, wherein said hydrazone compond is represented by formula (2) wherein R 21 is methyl, ethyl, propyl, phenyl, dialkylaminophenyl or benzyl.
Claim 11
Dependent Claim
33 words
An electrophotographic photosensitive member of claim 1, wherein said hydrazone compound is represented by formula (2) where at least one of R 22 and R 23 is phenyl, tolyl, alkoxyphenyl, α-naphthyl, or β-naphthyl.
Claim 12
Dependent Claim
30 words
An electrophotographic photosensitive member of claim 10, wherein said hydrazone compound is represented by formula (2) where R 23 is methyl, ethyl, 2-hydroxyethyl, phenyl, tolyl, alkoxyphenyl, benzyl, α-naphthyl or β-naphthyl.
Claim 13
Dependent Claim
19 words
An electrophotographic photosensitive member of claim 1, wherein a layer containing said hydrazone compound is a charge transport layer.
Claim 14
Dependent Claim
20 words
An electrophotographic photosensitive member of claim 12, wherein a charge generation layer is provided contiguously to said charge transport layer.
Claim 15
Dependent Claim
19 words
An electrophotographic photosensitive member of claim 13, wherein said charge transport layer is laid on the charge generation layer.
Claim 16
Dependent Claim
18 words
An electrophotographic photosensitive member of claim 14, wherein said charge generation layer is laid on a conductive layer.
Claim 17
Dependent Claim
20 words
An electrophotographic photosensitive member of claim 15, wherein an intermediary layer is provided between said charge generation and conductive layers.
Claim 18
Dependent Claim
41 words
An electrophotographic photosensitive member of claim 12, wherein said charge transport layer contains at least one selected from acrylic resins, methacrylic resins, vinyl chloride resin, vinyl acetate resin, phenolic resins, epoxy resins, polyester resins, alkyd resins, polycarbonate resin, and polyurethane resins.
Claim 19
Dependent Claim
17 words
An electrophotographic photosensitive member of claim 17, wherein said charge transport layer has a thickness of 2-100μ.
Claim 20
Dependent Claim
17 words
An electrophotographic photosensitive member of claim 18, wherein said charge transport layer has a thickness of 5-30μ.
Claim 21
Dependent Claim
52 words
An electrophotographic photosensitive member of claim 13, wherein said charge generation layer contains at least one of selenium, selenium-tellurium, pyrylium dyes, thiopyrylium dyes, phthalocyanine pigments, anthoanthrone pigments, dibenzopyrene quinone pigments, pyranthrone pigments, trisazo pigments, disazo pigments, monoazo pigments, indigo pigments, quinacridone pigments, asymmetric quinocyanine dyes, quinocyanine dyes, perylene pigments, and amorphous silicon.
Claim 22
Dependent Claim
24 words
An electrophotographic photosensitive member of claim 20, wherein said charge generation layer comprises a vacuum deposit layer of selenium, selenium-tellurium, or a perylene pigment.
Claim 23
Dependent Claim
21 words
An electrophotographic photosensitive member of claim 20, wherein said charge generation layer comprises a trisazo or disazo pigment and a binder.
Claim 24
Dependent Claim
36 words
An electrophotographic photosensitive member of claim 22, wherein said binder is at least one of poly(vinyl butyral), poly(methyl methacrylate), polystyrene, poly(vinylidene chloride), chlorinated rubber, polyvinyltoluene, styrene-maleic anhydride copolymer, polyesters, poly(vinyl chloride), ethylcellulose, polyamides and styrene-butadiene copolymer.
Claim 25
Dependent Claim
13 words
An electrophotographic photosensitive member of claim 23, wherein said binder is poly(vinyl butyral).
Claim 26
Dependent Claim
20 words
An electrophotographic photosensitive member of claim 20, wherein said charge generation layer comprises amorphous silicon layer prepared by glow discharge.
Claim 27
Dependent Claim
17 words
An electrophotographic photosensitive member of claim 13, wherein said charge generation layer has a thickness of 0.005-20μ.
Claim 28
Dependent Claim
17 words
An electrophotographic photosensitive member of claim 26, wherein said charge generation layer has a thickness of 0.05-10μ.
References Cited (Backward Citations)
US3180729A
Cited
GB930988A
Cited
US3378554A
Cited
US3484237A
Cited
GB1296390A
Cited
US3684502A
Cited
US3870516A
Cited
US3877935A
Cited
US3894868A
Cited
GB1370197A
Cited
JPS4871236A
Cited
US3871882A
Cited
US3884691A
Cited
US3775105A
Cited
US3824099A
Cited
US3837851A
Cited
DE2302522A1
Cited
GB1465141A
Cited
GB1465142A
Cited
GB1453024A
Cited
JPS5194829A
Cited
US4279981A
Cited
US4272598A
Cited
US4251614A
Cited
GB2001769A
Cited
US4260672A
Cited
US4150987A
Cited
US4265991A
Cited
JPS54112637A
Cited
GB2018446A
Cited
JPS54119925A
Cited
JPS54121742A
Cited
US4278747A
Cited
US4367273A
Cited
JPS5517105A
Cited
GB2034493A
Cited
US4365014A
Cited
GB2034494A
Cited
US4338388A
Cited
US4256821A
Cited
GB2055803A
Cited
GB2052082A
Cited
US4297426A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-05-01 | 1987-10-31 | 1988-05-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-05-01 | 1991-10-31 | 1992-05-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-05-01 | 1995-10-31 | 1996-05-01 | $7700.00 | Window Closed / Lapsed |