Canon Kabushiki Kaisha

Copyer Kabushiki Kaisha

Minoru Mabuchi

Kiyoshi Sakai

Shozo Ishikawa

Yoshio Takasu

Makoto Kitahara

Katsunori Watanabe

Shoji Umehara

Tetsuo Arita

Masataka Yamashita

Naoto Fujimura

Masakazu Matsumoto

Masaki Kuribayashi

Hideyuki Takahashi

Norie Takebayashi

Yuji Egarashi

Toshiko Suzuki

Yuji Egashira

A process for synthesizing an N,N-disubstituted hydrazone comprises carrying out nitrozation by adding an aqueous solution of sodium nitrite to a solution having one part by weight of an N,N-disubstituted amine dissolved in 3 to 30 parts by weight of an organic acid, then reducing the nitrozated product to an N,N-disubstituted hydrazine by adding a reducing agent to the mixture containing the nitrozated product, and thereafter adding to the mixture containing the N,N-disubstituted hydrazine a carbonyl compound of the formula: ##STR1## wherein A represents an aromatic hydrocarbon group or an aromatic heterocyclic group which may have a substituent, B represents a hydrogen atom, an alkyl group, an aryl group or an aromatic heterocyclic group, which may have a substituent, thereby performing condensation of the N,N-disubstituted hydrazine with the carbonyl compound.

Process for synthesis of N,N-disubstituted hydrazone

An electrophotographic photosensitive member comprises a conductive support, and a photosensitive layer containing as azo pigment as a charge-generating material, wherein in a powder X-ray diffraction pattern of the azo pigment contained in said photosensitive layer the ratio (X) of the diffracted beam intensity at a maximum peak at 2.theta. of from 5.degree. to 20.degree. to the X-ray intensity at the background is 0.8 or more, provided that:

Electrophotographic photsensitive member

An electrophotographic photosensitive member comprises at least a charge generation layer and a charge transport layer on an electroconductive substrate, wherein said charge generation layer contains, as a binder, a polyvinylacetal resin obtained by acetalization reaction of polyvinyl alcohol and aldehyde compound represented by the following general formula:

Electrophotographic photosensitive member containing polyvinylarylal

An improved electrophotographic photosensitive member is composed of a layer containing a hydrazone compound represented by the formula ##STR1## wherein R.sub.2 and R.sub.3 are each unsubstituted alkyl or substituted alkyl, unsubstituted aralkyl or substituted aralkyl, or unsubstituted aryl or substituted aryl, with the proviso that R.sub.2 and R.sub.3 are not simultaneously alkyls, n is 1 or 2, when n is 1, A represents ##STR2## wherein R.sub.1 is C.sub.1 -C.sub.5 alkyl, unsubstituted aralkyl, or substituted aralkyl, and when n is 2, A represents a direct single bond between two ##STR3## radicals.

Electrophotographic photosensitive member

An organic film comprising at least one compound of the following formulae (1)-(5): ##STR1## wherein R.sub.11 and R.sub.13 each represent substituted or unsubstituted aryl, R.sub.12 represents substituted or unsubstituted arylene, and A.sup..crclbar. represents an anionic residue; ##STR2## wherein R.sub.21, R.sub.22, and R.sub.24 each represent substituted or unsubstituted aryl, R.sub.23 represents substituted or unsubstituted arylene, and A.sup..crclbar. represents an anionic residue; ##STR3## wherein R.sub.31, R.sub.33, and R.sub.35 each represent substituted or unsubstituted aryl, R.sub.32 and R.sub.34 each represent substituted or unsubstituted arylene, and A.sup..crclbar. represents an anionic residue; ##STR4## wherein R.sub.41 represents alkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted styryl, R.sub.42 represents substituted or unsubstituted arylene, R.sub.43 represents substituted or unsubstituted aryl, and A.sup..crclbar. represents an anionic residue; and ##STR5## wherein R.sub.51 represents alkoxy, R.sub.52 represents alkyl, R.sub.53 represents substituted or unsubstituted arylene, R.sub.54 represents substituted or unsubstituted aryl, A.sup..crclbar. represents an anionic residue, and n represents an integer of 1 or 2.

Recording medium and process employing a photosensitive organic film

An electrophotographic photosensitive member comprises a layer containing a binder and at least one hydrazone compound represented by the following formula (1), (2), (3), (4), or (5): ##STR1##

Electrophotographic photosensitive member having a photosensitive layer

An electrophotographic photosensitive member is characterized by having a layer which contains at least one hydrazone compound represented by the following formula (1) or (2): ##STR1## wherein R.sub.11 represents substituted or unsubstituted naphthyl; R.sub.12 represents substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R.sub.13 represents hydrogen, alkyl, or alkoxy; R.sub.14 and R.sub.15 each represent substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; n is 0 or 1; when n=1, R.sub.14 and R.sub.15, together with the nitrogen which links them, may complete a cyclic amino group; X represents a group necessary for completing a benzene ring or naphthalene ring; R.sub.21 and R.sub.22 each represent hydrogen, halogen, alkyl, alkoxy or disalkylamino; and R.sub.23, R.sub.24, R.sub.25, R.sub.26 and R.sub.27 each represent substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl.

Electrophotographic member having layer containing methylidenyl

An electrophotographic photosensitive member is characterized by having a layer containing at least one of hydrazone group compounds represented by the following formula (1) or of ketazine group compounds represented by the following formula (2): ##STR1## In the formula, R.sub.11 and R.sub.12 independently of one another represent hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic radical; R.sub.13 and R.sub.14 independently of one another represent subsituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic radical; and R.sub.15 represents a divalent organic residue. ##STR2## In the formula, R.sub.21, R.sub.22, R.sub.23, and R.sub.24 independently one another represent substituted or unsubstituted alkyl, substituted or substituted aralkyl, or substituted or unsubstituted aryl, or R.sub.21 and R.sub.22, together with the nitrogen which links them, represent cyclic amino radical, and R.sub.23 and R.sub.24, together with the nitrogen which links them, represent cyclic amino radical.

Electrophotographic member with hydrazone or ketazine compounds

An electrophotographic photosensitive member is characterized by having a layer containing at least one hydrazone compound represented by the following formula [I] or [II]: ##STR1## wherein R.sub.11 and R.sub.12 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino, provided that at least one of R.sub.11 and R.sub.12 is substituted amino or alkoxy; R.sub.13 and R.sub.14 represent substituted or unsubstituted alkyl or substituted or unsubstituted aryl, provided that at least one of R.sub.13 and R.sub.14 is substituted or unsubstituted aryl, or R.sub.13 and R.sub.14, together with the nitrogen atom which links them, represent a nitrogen-containing heterocyclic ring; R.sub.15, R.sub.16, R.sub.17, and R.sub.18 represent hydrogen, halogen, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, or substituted amino; m and n represent 0 or 1; R.sub.21 and R.sub.22 represent substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or R.sub.21 and R.sub.22, together with the nitrogen atom which links them, represent a five- or six-membered ring; R.sub.23 and R.sub.24 represent substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or R.sub.23 and R.sub.24, together with the nitrogen atom which links them, represent a five- or six-membered ring; R.sub.25 and R.sub.26 represent hydrogen, halogen, nitro, substituted or unsubstituted alkyl, alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted acyl, or substituted or unsubstituted amino; and R represents divalent organic residue.

An electrophotographic photosensitive member having a layer containing at least one compound represented by the formula ##STR1## wherein X.sub.1 represents a residue necessary for completing a substituted or unsubstituted aromatic hydrocarbon ring; X.sub.2 represents a residue necessary for completing a substituted or unsubstituted heterocyclic ring; R.sub.1, R.sub.2, R.sub.3, and A each represent hydrogen, alkyl, aralkyl, or aryl, substituted or unsubstituted; and m is 0 or 1.

Electrophotographic photosensitive member with hydrazone compound

An electrophotographic photosensitive member comprises a layer containing at least one member of the hydrazone compounds of the formula: ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, and substituted or unsubstituted aryl, and R.sub.1 and R.sub.2 can not be simultaneously alkyl; and R.sub.4 is substituted or unsubstituted aryl.

Growing community of inventors

Tokyo, Japan

Minoru Mabuchi