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US4241157A Expired / Lapsed US ⏱️ 0.0 years remaining

Organic heterocyclic electrophotosensitive materials for migration imaging processes

Assignee: Eastman Kodak Co
•
Filing: 1978-08-21
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Granted: 1980-12-23
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Expires: 1998-08-21
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Abstract

Abstract Electrophotosensitive materials having the structure ##STR1## wherein: r and s may be zero, one two or three; R 1 and R 2 may be the same or different and each may represent hydrogen, alkyl, aryl, alkoxyalkyl or alkoxyaryl; Y represents O or S; L 1 , L 2 , L 3 , L 4 and L 5 may be the same or different, represent hydrogen, alkyl, aryl or aralkyl and in addition either L 1 and L 2 or any two of L 3 , L 4 and L 5 , together with the atoms to which they are attached, may represent the elements needed to complete a carbocyclic ring; A 1 and A 2 represent a substituted or unsubstituted heterocyclic nucleus.

Inventors

  • 👤 Frank G. Webster
  • 👤 Michael T. Regan

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 15:26
CPC Classifications
G; G03; G03G; G03G17/00; G03G17/04

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 334 words
An electrophoretic migration imaging process which comprises subjecting an electrically photosensitive colorant material positioned between at least two electrodes to an applied electric field and exposing said materials to an image pattern of radiation to which the material is photosensitive, thereby obtaining image formation of said electrically photosensitive materials on at least one of said electrodes, wherein at least a portion of said electrically photosensitive colorant material is an electrically photosensitive material having one of the following structures: ##STR42## r and s may be zero, one two or three; R 1 and R 2 may be the same or different and each may represent hydrogen, alkyl, aryl, alkoxyalkyl or alkoxyaryl; Y represents O or S; L 1 , L 2 , L 3 , L 4 and L 5 , which may be the same or different, represent hydrogen, alkyl, aryl or aralkyl and in addition either L 1 and L 2 or any two of L 3 , L 4 and L 5 , together with the atoms to which they are attached, may represent the elements needed to complete a carbocyclic ring; A 1 represents napthoquinolizine, acridine, quinazoline, or an N-substituted nucleus selected from the group consisting of imidazole, 3H-indole, thiazole, benzothiazole, naphthothiazole, dioxolobenzothiazole, thianaphtheno-7',6',4,5-thiazole, oxazole, naphthoxazole, selenazole, benzoselenazole, naphthoselenazole, thiazoline, 2-quinoline, 4-quinoline, 1-isoquinoline, benzimidazole, 2-pyridine, 4-pyridine, triazolobenzothiazole, quinolizine or tetrazole; A 2 represents a heterocyclic nucleus as defined for A 1 and in addition represents aryl or a heterocyclic nucleus selected from the group consisting of benzo[b]thiophene, naphtho[2,3-b]thiophene, furan, isobenzofuran, chromene, pyran, xanthene, pyrrole, 2H-pyrrole, pyrazole, indolizine, indoline, indole, indazole, carbazole, pyrimidine, isothiazole, isoxazole, furazan, chroman, isochroman, tetrahydroquinoline, 4H-pyrrolo[3,2,1-ij]quinoline, dihydro-4H-pyrrolo[3,2,1-ij]-quinoline; tetrahydro-4H-pyrrolo[3,2,1-ih]quinoline; 1H,5H-benzo[ij]quinolizine; dihydro 1H,5H-benzo[ij]quinolizine and tetrahydro-1H,5H-benzo[ij]quinolizine, dihydro-9H-benzo[a]-xanthen-8-yl; dihydro-5H-benzo[b]pyran-7-yl; said N-substituents are selected from the group consisting of alkyl, aryl, haloaryl and dialkylamino; and A 1 and A 2 may be further substituted by one or more substituents selected from the group consisting of hydrogen, alkyl, aryl, alkylaryl, alkoxy, aryloxy, halogen, nitro, oxo, haloaryl, dialkylamino, diarylamino or A 1 (CH--CH) r .
Claim 2
Dependent Claim 334 words
An electrophoretic migration imaging process which comprises subjecting an electrically photosensitive colorant material positioned between at least two electrodes to an applied electric field and exposing said materials to an image pattern of radiation to which the material is photosensitive, thereby obtaining image formation of said electrically photosensitive materials on at least one of said electrodes, wherein at least a portion of said electrically photosensitive colorant material is an electrically photosensitive material having one of the following structures: ##STR42## r and s may be zero, one two or three; R 1 and R 2 may be the same or different and each may represent hydrogen, alkyl, aryl, alkoxyalkyl or alkoxyaryl; Y represents O or S; L 1 , L 2 , L 3 , L 4 and L 5 , which may be the same or different, represent hydrogen, alkyl, aryl or aralkyl and in addition either L 1 and L 2 or any two of L 3 , L 4 and L 5 , together with the atoms to which they are attached, may represent the elements needed to complete a carbocyclic ring; A 1 represents napthoquinolizine, acridine, quinazoline, or an N-substituted nucleus selected from the group consisting of imidazole, 3H-indole, thiazole, benzothiazole, naphthothiazole, dioxolobenzothiazole, thianaphtheno-7',6',4,5-thiazole, oxazole, naphthoxazole, selenazole, benzoselenazole, naphthoselenazole, thiazoline, 2-quinoline, 4-quinoline, 1-isoquinoline, benzimidazole, 2-pyridine, 4-pyridine, triazolobenzothiazole, quinolizine or tetrazole; A 2 represents a heterocyclic nucleus as defined for A 1 and in addition represents aryl or a heterocyclic nucleus selected from the group consisting of benzo[b]thiophene, naphtho[2,3-b]thiophene, furan, isobenzofuran, chromene, pyran, xanthene, pyrrole, 2H-pyrrole, pyrazole, indolizine, indoline, indole, indazole, carbazole, pyrimidine, isothiazole, isoxazole, furazan, chroman, isochroman, tetrahydroquinoline, 4H-pyrrolo[3,2,1-ij]quinoline, dihydro-4H-pyrrolo[3,2,1-ij]-quinoline; tetrahydro-4H-pyrrolo[3,2,1-ih]quinoline; 1H,5H-benzo[ij]quinolizine; dihydro 1H,5H-benzo[ij]quinolizine and tetrahydro-1H,5H-benzo[ij]quinolizine, dihydro-9H-benzo[a]-xanthen-8-yl; dihydro-5H-benzo[b]pyran-7-yl; said N-substituents are selected from the group consisting of alkyl, aryl, haloaryl and dialkylamino; and A 1 and A 2 may be further substituted by one or more substituents selected from the group consisting of hydrogen, alkyl, aryl, alkylaryl, alkoxy, aryloxy, halogen, nitro, oxo, haloaryl, dialkylamino, diarylamino or A 1 (CH--CH) r .
Claim 3
Dependent Claim 29 words
A process according to claim 1, wherein A 1 is a nucleus selected from the group consisting of benzothiazole, naphthothiazole, triazolobenzothiazole, quinolizine, tetrazole, napthoquinolizine, acridine, quinazoline, napthoquinolizine and thiazoline.
Claim 4
Dependent Claim 13 words
A process according to claim 1 or 2 wherein A 2 is tetrahydro-1H,5H-benzo[ij]-quinolizine.
Claim 5
Dependent Claim 19 words
A process according to claim 2 wherein said material has a structure selected from the group consisting of: ##STR43##
Claim 6
Dependent Claim 282 words
An electrophoretic migration imaging dispersion comprising an electrically insulating carrier, a charge control agent and an electrically photosensitive material having one of the following structures ##STR44## r and s may be zero, one, two or three; R 1 and R 2 may be the same or different and each may represent hydrogen, alkyl, aryl, alkoxyalkyl or alkoxyaryl; Y represents O or S; L 1 , L 2 , L 3 , L 4 and L 5 , which may be the same or different, represent hydrogen, alkyl, aryl or aralkyl and in addition either L 1 and L 2 or any two of L 3 , L 4 and L 5 , together with the atoms to which they are attached, may represent the elements needed to complete a carbocyclic ring; A 1 represents napthoquinolizine, acridine, quinazoline, or an N-substituted nucleus selected from the group consisting of imidazole, 3H-indole, thiazole, benzothiazole, naphthothiazole, dioxolobenzothiazole, thianaphtheno-7',6',4,5-thiazole, oxazole, benzoxazole, naphthoxazole, selenazole, benzoselenazole, naphthoselenazole, thiazoline, 2-quinoline, 4-quinoline, 1-isoquinoline, benzimidazole, 2-pyridine, 4-pyridine, triazolobenzothiazole, quinolizine or tetrazole; A 2 represents a heterocyclic nucleus as defined for A 1 and in addition represents aryl or a heterocyclic nucleus selected from the group consisting of benzo[b]thiophene, naphtho[2,3-b]thiophene, furan, isobenzofuran, chromene, pyran, xanthene, pyrrole, 2H-pyrrole, pyrazole, indolizine, indoline, indole, indazole, carbazole, pyrimidine, isothiazole, isoxazole, furazan, chroman, isochroman, tetrahydroquinoline, 4H-pyrrolo[3,2,1-ij]quinoline, dihydro-4H-pyrrolo[3,2,1-ij]-quinoline; tetrahydro-4H-pyrrolo[3,2,1-ih]quinoline; 1H,5H-benzo[ij]quinolizine; dihydro 1H,5H-benzo[ij]quinolizine and tetrahydro-1H,5H-benzo[ij]quinolizine, dihydro-9H-benzo[a]-xanthen-8-yl; dihydro-5H-benzo[b]pyran-7-yl; said N-substituents are selected from the group consisting of alkyl, aryl, haloaryl and dialkylamino; and A 1 and A 2 may be further substituted by one or more substituents selected from the group consisting of hydrogen, alkyl, aryl, alkylaryl, alkoxy, aryloxy, halogen, nitro, oxo, haloaryl, dialkylamino, diarylamino or A 1 (CH--CH) r .
Claim 7
Dependent Claim 282 words
An electrophoretic migration imaging dispersion comprising an electrically insulating carrier, a charge control agent and an electrically photosensitive material having one of the following structures ##STR44## r and s may be zero, one, two or three; R 1 and R 2 may be the same or different and each may represent hydrogen, alkyl, aryl, alkoxyalkyl or alkoxyaryl; Y represents O or S; L 1 , L 2 , L 3 , L 4 and L 5 , which may be the same or different, represent hydrogen, alkyl, aryl or aralkyl and in addition either L 1 and L 2 or any two of L 3 , L 4 and L 5 , together with the atoms to which they are attached, may represent the elements needed to complete a carbocyclic ring; A 1 represents napthoquinolizine, acridine, quinazoline, or an N-substituted nucleus selected from the group consisting of imidazole, 3H-indole, thiazole, benzothiazole, naphthothiazole, dioxolobenzothiazole, thianaphtheno-7',6',4,5-thiazole, oxazole, benzoxazole, naphthoxazole, selenazole, benzoselenazole, naphthoselenazole, thiazoline, 2-quinoline, 4-quinoline, 1-isoquinoline, benzimidazole, 2-pyridine, 4-pyridine, triazolobenzothiazole, quinolizine or tetrazole; A 2 represents a heterocyclic nucleus as defined for A 1 and in addition represents aryl or a heterocyclic nucleus selected from the group consisting of benzo[b]thiophene, naphtho[2,3-b]thiophene, furan, isobenzofuran, chromene, pyran, xanthene, pyrrole, 2H-pyrrole, pyrazole, indolizine, indoline, indole, indazole, carbazole, pyrimidine, isothiazole, isoxazole, furazan, chroman, isochroman, tetrahydroquinoline, 4H-pyrrolo[3,2,1-ij]quinoline, dihydro-4H-pyrrolo[3,2,1-ij]-quinoline; tetrahydro-4H-pyrrolo[3,2,1-ih]quinoline; 1H,5H-benzo[ij]quinolizine; dihydro 1H,5H-benzo[ij]quinolizine and tetrahydro-1H,5H-benzo[ij]quinolizine, dihydro-9H-benzo[a]-xanthen-8-yl; dihydro-5H-benzo[b]pyran-7-yl; said N-substituents are selected from the group consisting of alkyl, aryl, haloaryl and dialkylamino; and A 1 and A 2 may be further substituted by one or more substituents selected from the group consisting of hydrogen, alkyl, aryl, alkylaryl, alkoxy, aryloxy, halogen, nitro, oxo, haloaryl, dialkylamino, diarylamino or A 1 (CH--CH) r .
Claim 8
Dependent Claim 29 words
A dispersion as in claim 5, wherein A 1 is a nucleus selected from the group consisting of benzothiazole, naphthothiazole, triazolobenzothiazole, quinolizine, tetrazole, napthoquinolizine, acridine, quinazoline, napthoquinolizine and thiazoline.
Claim 9
Dependent Claim 13 words
A dispersion as in claims 5 or 6 wherein A 2 is tetrahydro-1H,5H-benzo[ij]-quinolizine.
Claim 10
Dependent Claim 19 words
A dispersion as in claim 5, wherein the electrically photosensitive material is selected from the group consisting of ##STR45##

References Cited (Backward Citations)

US3384566A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-12-23 1984-06-23 1984-12-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-12-23 1988-06-23 1988-12-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-12-23 1992-06-23 1992-12-23 $7700.00 Window Closed / Lapsed

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