US4390611A — Electrophotographic photosensitive azo pigment co…

Claim 1

Independent Claim 38 words

An electrophotographic photosensitive member comprising a conductive support, a charge transport layer, and a charge generating layer comprising azo pigments having at least one azo group linked to a coupler residue represented by the following formula or: ##STR171##

Claim 2

Dependent Claim 38 words

An electrophotographic photosensitive member comprising a conductive support, a charge transport layer, and a charge generating layer comprising azo pigments having at least one azo group linked to a coupler residue represented by the following formula or: ##STR171##

Claim 3

Dependent Claim 42 words

An electrophotographic photosensitive member according to claim 1, wherein said electrophotographic photosensitive member is composed of multilaminate structure comprising a conductive support, a bond layer, a charge generation layer, and a charge transport layer, the layers being laminated in the above-mentioned order.

Claim 4

Dependent Claim 53 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigments are disazo pigments represented by the formula ##STR172## wherein R 1 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R 2 is substituted or unsubstituted aryl; and A 1 is a divalent organic residue.

Claim 5

Dependent Claim 57 words

An electrophotographic photosensitive member according to claim 3, wherein said azo pigments are disazo pigments represented by the following formula (1)' or (1)": ##STR173## wherein R 1 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R 2 is substituted or unsubstituted aryl; and A 1 is a divalent organic residue.

Claim 6

Dependent Claim 23 words

An electrophotographic photosensitive member according to claim 4, wherein said A 1 is a divalent hydrocarbon radical having at least one benzene ring.

Claim 7

Dependent Claim 56 words

An electrophotographic photosensitive member according to claim 5, wherein said A 1 is a divalent organic residue selected from the group consisting of phenylene, naphthylene, ##STR174## wherein R 5 is hydrogen or cyano, R 6 is hydrogen or alkoxy, and R 7 and R 8 independently of one another represent hydrogen, halogen, alkyl, alkoxy, or nitro.

Claim 8

Dependent Claim 24 words

An electrophotographic photosensitive member according to claim 6, wherein said A 1 is a divalent organic residue selected from the group consisting of ##STR175##

Claim 9

Dependent Claim 24 words

An electrographic photosensitive member according to claim 4, wherein said A 1 is a nitrogen-containing divalent hydrocarbon radical having at least two benzene rings.

Claim 10

Dependent Claim 25 words

An electrophotographic photosensitive member according to claim 8, wherein said A 1 is a nitrogen-containing divalent hydrocarbon radical selected from the group consisting of ##STR176##

Claim 11

Dependent Claim 28 words

An electrophotographic photosensitive member according to claim 4, wherein said A 1 is a divalent hydrocarbon radical having at least two benzene rings and at least one hetero-ring.

Claim 12

Dependent Claim 133 words

An electrophotographic photosensitive member according to claim 10, wherein said A 1 is a divalent organic residue selected from the group consisting of ##STR177## wherein, Z is oxygen, sulfur, or >N-R 18 (R 18 : hydrogen or lower alkyl); R 9 is hydrogen, halogen, or lower alkyl; R 10 is hydrogen, halogen, lower alkyl, alkoxy, hydroxy, nitro, dialkylamino, or acylamino; n is 0 or 1; m is an integer of 1-4; R 11 and R 12 independently of one another represent hydrogen, lower alkyl, or halogen; R 13 is single bond, substituted or unsubstituted phenylene, or substituted or unsubstituted vinylene; R 14 and R 15 independently of one another represent hydrogen, halogen, lower alkyl; and R 16 and R 17 independently of one another represent hydrogen, halogen, lower alkyl, alkoxy, nitro, or acylamino.

Claim 13

Dependent Claim 24 words

An electrophotographic photosensitive member according to claim 11, wherein said A 1 is a divalent organic residue selected from the group consisting of ##STR178##

Claim 14

Dependent Claim 53 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigments are trisazo pigments represented by the formula ##STR179## wherein R 1 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R 2 is substituted or unsubstituted aryl; and A 2 is a trivalent organic residue.

Claim 15

Dependent Claim 53 words

An electrophotographic photosensitive member according to claim 13, wherein said azo pigments are trisazo pigments represented by the formula ##STR180## wherein R 1 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R 2 is substituted or unsubstituted aryl; and A 2 is a trivalent organic residue.

Claim 16

Dependent Claim 24 words

An electrophotographic photosensitive member according to claim 14, wherein said A 2 is a nitrogen-containing trivalent hydrocarbon radical having at least two benzene rings.

Claim 17

Dependent Claim 17 words

An electrophotographic photosensitive member according to claim 15, wherein said A 2 is the following radical: ##STR181##

Claim 18

Dependent Claim 28 words

An electrophotographic photosensitive member according to claim 14, wherein said A 2 is a trivalent hydrocarbon radical having at least two benzene rings and at least one hetero-ring.

Claim 19

Dependent Claim 24 words

An electrophotographic photosensitive member according to claim 17, wherein said A 2 is a trivalent organic residue selected from the group consisting of ##STR182##

Claim 20

Dependent Claim 53 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigments are disazo pigments represented by the formula ##STR183## wherein, R 3 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R 4 is substituted or unsubstituted aryl; and A 1 is a divalent organic residue.

Claim 21

Dependent Claim 53 words

An electrophotographic photosensitive member according to claim 19, wherein said azo pigments are disazo pigments represented by the formula ##STR184## wherein R 3 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R 4 is substituted or unsubstituted aryl; and A 1 is a divalent organic residue.

Claim 22

Dependent Claim 23 words

An electrophotographic photosensitive member according to claim 20, wherein said A 1 is a divalent hydrocarbon radical having at least one benzene ring.

Claim 23

Dependent Claim 55 words

An electrophotographic photosensitive member according to claim 21, wherein said A 1 is a divalent organic residue selected from the group consisting of phenylene, naphthylene, ##STR185## wherein R 5 is hydrogen or cyano, R 6 is hydrogen or alkoxy, R 7 and R 8 independently of one another represent hydrogen, halogen, alkyl, alkoxy, or nitro.

Claim 24

Dependent Claim 24 words

An electrophotographic photosensitive member according to claim 22, wherein said A 1 is a divalent organic residue selected from the group consisting of ##STR186##

Claim 25

Dependent Claim 24 words

An electrophotographic photosensitive member according to claim 20, wherein said A 1 is a nitrogen-containing divalent hydrocarbon radical having at least two benzene rings.

Claim 26

Dependent Claim 25 words

An electrophotographic photosensitive member according to claim 24, wherein said A 1 is a nitrogen-containing divalent hydrocarbon radical selected from the group consisting of ##STR187##

Claim 27

Dependent Claim 28 words

An electrophotographic photosensitive member according to claim 20, wherein said A 1 is a divalent hydrocarbon radical having at least two benzene rings and at least one hetero-ring.

Claim 28

Dependent Claim 134 words

An electrophotographic photosensitive member according to claim 26, wherein said A 1 is a divalent organic residue selected from the group consisting of ##STR188## wherein Z is oxygen, sulfur, or N-R 18 (R 18 : hydrogen or lower alkyl); R 9 is hydrogen, halogen, or lower alkyl; R 10 is hydrogen, halogen, lower alkyl, alkoxy, hydroxy, nitro, dialkylamino, or acylamino; n is 0 or 1; m is an integer of 1-4; R 11 and R 12 independently of one another represent hydrogen, lower alkyl, or halogen; R 13 is single bond, substituted or unsubstituted phenylene, or substituted or unsubstituted vinylene; R 14 and R 15 independently of one another represent hydrogen, halogen, or lower alkyl; and R 16 and R 17 independently of one another represent hydrogen, halogen, lower alkyl, alkoxy, nitro, or acylamino.

Claim 29

Dependent Claim 24 words

An electrophotographic photosensitive member according to claim 27, wherein said A 1 is a divalent organic residue selected from the group consisting of ##STR189##

Claim 30

Dependent Claim 53 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigments are trisazo pigments represented by the formula ##STR190## wherein R 3 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R 4 is substituted or unsubstituted aryl; and A 2 is a trivalent organic residue.

Claim 31

Dependent Claim 53 words

An electrophotographic photosensitive member according to claim 29, wherein said azo pigments are trisazo pigments represented by the formula ##STR191## wherein R 3 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R 4 is substituted or unsubstituted aryl; and A 2 is a trivalent organic residue.

Claim 32

Dependent Claim 24 words

An electrophotographic photosensitive member according to claim 30, wherein said A 2 is a nitrogen-containing trivalent hydrocarbon radical having at least two benzene rings.

Claim 33

Dependent Claim 17 words

An electrophotographic photosensitive member according to claim 31, wherein said A 2 is the following radical: ##STR192##

Claim 34

Dependent Claim 28 words

An electrophotographic photosensitive member according to claim 30, wherein said A 2 is a trivalent hydrocarbon radical having at least two benzene rings and at least one hetero-ring.

Claim 35

Dependent Claim 24 words

An electrophotographic photosensitive member according to claim 33, wherein said A 2 is a trivalent organic residue selected from the group consisting of ##STR193##

Claim 36

Dependent Claim 17 words

An electrophotographic photosensitive member according to claim 1 or 2, wherein said charge generation layer contains binders.

Claim 37

Dependent Claim 57 words

An electrophotographic photosensitive member according to claim 35, wherein said charge generation layer contains as a binder at least one kind of high-molecular material selected from the group consisting of poly (vinyl butyral) poly (vinyl acetate), polyesters, polycarbonates, phenoxy resins, acrylic resins, polyacrylamide, polyamides, poly (vinylpyridine), cellulosic resins, urethane resins, epoxy resins, casein, and poly (vinyl alcohol).

Claim 38

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 35, wherein said charge generation layer contains poly (vinyl butyral) as a binder.

Claim 39

Dependent Claim 19 words

An electrophotographic photosensitive member according to claim 35, wherein said charge generation layer contains polyester resins as a binder.

Claim 40

Dependent Claim 18 words

An electrophotographic photosensitive member according to claim 35, wherein said charge generation layer contains polycarbonates as a binder.

Claim 41

Dependent Claim 34 words

An electrophotographic photosensitive member according to claim 1 or 2, wherein said charge transport layer contains at least one compound selected from the group consisting of hydrazones, pyrazolines, diarylalkanes, triarylalkanes, oxadiazoles, anthracenes, and oxazoles.

Claim 42

Dependent Claim 40 words

An electrophotographic photosensitive member according to claim 40, wherein said charge transport layer contains at least one pyrazoline compound selected from the group consisting of 1-phenyl-3-(4-N,N-diethylaminostyryl)-5-(4-N,N-diethylaminophenyl) pyrazoline, 1-[pyridyl-(2)-3-(4-N,N-diethylaminostyryl)-5-(4-N,N-diethylaminophenyl) pyrazoline, 1-[quinolyl-(2)]-3-(4-N,N-diethylaminostyryl)-5-(4-N,N-diethylaminophenyl) pyrazoline, 1-[quinolyl-(4)]-3-(4-N,N-diethylaminostyryl)-5-(4-N,N-diethylaminophenyl) pyrazoline, 1-[pyridyl-(3)]-3-(4-N,N-diethylaminostyryl)-5-(4-N,N-diethylaminophenyl) pyrazoline, 1-[3-methoxypyridyl-(2)]-3-(4-N,N-diethylaminostyryl)-5-(4-N,N-diethylaminophenyl) pyrazoline, and 1-[lepidyl-(2)]-3-(4-N,N-diethylaminostyryl)-5-(4-N,N-diethylaminophenyl) pyrazoline.

Claim 43

Dependent Claim 28 words

An electrophoto-raphic photosensitive member according to claim 40, wherein said charge transport layer contains at least one hydrazone compound selected from the group consisting of 4-N,N-diethylaminobenzaldehyde-N-N-diphenylhydrazone, and N-N-diphenylhydrazino-3-methylidene-9-ethylcarbazol.

Claim 44

Dependent Claim 15 words

An electrophotographic photosensitive member according to claim 40, wherein said charge transport layer contains 2,5-bis-(4-N,N-diethylaminophenyl)-1,3,4oxadiazole.

Claim 45

Dependent Claim 33 words

An electrophotographic photosensitive member according to claim 40, wherein said charge transport layer contains at least one anthracene compound selected from the group consisting of 9-styrylanthracene,9-(4-N,N-dimethylaminostyryl)-anthracene, 9-(4-N,N-diethylaminostyryl) anthracene, 9-(4-N,N-dibenzylaminostyryl) anthracene, and 4-bromo-9-(4-N,N-diethylaminostyryl) anthracene.

Claim 46

Dependent Claim 35 words

An electrophotographic photosensitive member according to claim 2, wherein said bond layer contains at least one high-molecular material selected from the group consisting of casein, pol (vinyl alcohol), water-soluble ethylene-acrylic acid copolymer, hydroxypropylcellulose, and nitrocellulose.

Claim 47

Dependent Claim 14 words

An electrophotographic photosensitive member according to claim 2, wherein said bond layer contains casein.

Claim 48

Dependent Claim 16 words

An electrophotographic photosensitive member according to claim 2, wherein said bond layer contains poly (vinyl alcohol).

Claim 49

Dependent Claim 19 words

An electrophotographic photosensitive member according to claim 2, said azo pigment is a disazo pigment of the structure ##STR194##

Claim 50

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR195##

Claim 51

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR196##

Claim 52

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR197##

Claim 53

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR198##

Claim 54

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR199##

Claim 55

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR200##

Claim 56

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR201##

Claim 57

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR202##

Claim 58

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR203##

Claim 59

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR204##

Claim 60

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR205##

Claim 61

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein, said azo pigment is a disazo pigment of the structure ##STR206##

Claim 62

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR207##

Claim 63

Dependent Claim 19 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is disazo pigment of the structure ##STR208##

Claim 64

Dependent Claim 20 words

An electrophotographic photosensitive member according to claim 1, wherein said azo pigment is a disazo pigment of the structure ##STR209##

Claim 65

Dependent Claim 75 words

An electrophotographic photosensitive member comprising a photosensitive layer comprising a binder, a charge-transport material, and azo pigments having at least one azo group linked to a coupler residue represented by the following formula [1] or [2]; ##STR210## wherein R 1 and R 3 independently represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl, and R 2 and R 4 independently represent substituted or unsubstituted aryl, and a conductive support.

Claim 66

Dependent Claim 75 words

An electrophotographic photosensitive member comprising a photosensitive layer comprising a binder, a charge-transport material, and azo pigments having at least one azo group linked to a coupler residue represented by the following formula [1] or [2]; ##STR210## wherein R 1 and R 3 independently represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl, and R 2 and R 4 independently represent substituted or unsubstituted aryl, and a conductive support.

Claim 67

Dependent Claim 31 words

An electrophotographic photosensitive member according to claim 64, wherein said charge transport material is a compound selected from the group consisting of fluorenones, hydrazones, pyrazolines, diarylalkanes, triarylalkanes, oxadiazoles, anthracenes, and oxazoles.

Claim 68

Dependent Claim 27 words

An electrophotographic photosensitive member according to claim 65, wherein said charge transport material is a compound selected from the group consisting of 2,5-bis(4-N,N-diethylaminophenyl)-1,3,4-oxadiazole, 2-(4-N,N-diethylaminophenyl)-4-(4-N,N-dimethylaminophenyl)-5-(2-chlorophenyl)oxazole, 2,4,7-trinitrofluorenone, and 4-N,N-diethylaminobenzaldehyde-N,N-diphenylhydrazone.

Claim 69

Dependent Claim 90 words

An electrophotographic process which comprises electrically charging an electrophotographic member, said member comprising a photosensitive layer comprising a binder, and azo pigments having at least one azo group linked to a coupler residue represented by the following formula [1] or [2]: ##STR211## wherein R 1 and R 3 independently represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl, and R 2 and R 4 independently represent substituted or unsubstituted aryl, and a conductive, support, and exposing said layer to form a latent electrostatic image.

Claim 70

Dependent Claim 90 words

An electrophotographic process which comprises electrically charging an electrophotographic member, said member comprising a photosensitive layer comprising a binder, and azo pigments having at least one azo group linked to a coupler residue represented by the following formula [1] or [2]: ##STR211## wherein R 1 and R 3 independently represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl, and R 2 and R 4 independently represent substituted or unsubstituted aryl, and a conductive, support, and exposing said layer to form a latent electrostatic image.

Claim 71

Dependent Claim 28 words

An electrophotographic process according to claim 67, wherein said electrophotographic member comprises a conductive support, a charge transport layer, and a charge generation layer containing said azo pigments.

Claim 72

Dependent Claim 52 words

An electrophotographic process according to claim 67, wherein said azo pigments are disazo pigments represented by the formula ##STR212## wherein R 1 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R 2 is substituted or unsubstituted aryl; and A 1 is a divalent organic residue.

Claim 73

Dependent Claim 52 words

An electrophotographic process according to claim 67, wherein said azo pigments are trisazo pigments represented by the formula ##STR213## wherein R 1 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R 2 is substituted or unsubstituted aryl; and A 2 is a trivalent organic residue.

Claim 74

Dependent Claim 52 words

An electrophotographic process according to claim 67, wherein said azo pigments are disazo pigments represented by the formula ##STR214## wherein, R 3 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R 4 is substituted or unsubstituted aryl; and A 1 is a divalent organic residue.

Claim 75

Dependent Claim 52 words

An electrophotographic process according to claim 67, wherein said azo pigments are trisazo pigments represented by the formula ##STR215## wherein R 3 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted aryl; R 4 is substituted or unsubstituted aryl; and A 2 is a trivalent organic residue.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1986-06-27	1986-12-27	1987-06-28	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1990-06-27	1990-12-27	1991-06-28	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1994-06-27	1994-12-27	1995-06-28	$7700.00	Window Closed / Lapsed

Electrophotographic photosensitive azo pigment containing members

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