CA1068970A - Utilisation d'un anhydride d'acide alicyclique dans un produit organique photoconducteur - Google Patents

Utilisation d'un anhydride d'acide alicyclique dans un produit organique photoconducteur

Info

Publication number: CA1068970A
Authority: CA; Canada
Prior art keywords: alicyclic; composition; coating; anhydride; photoconductive
Prior art date: 1974-08-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA233,538A

Other languages

English (en)

Inventor

Denis J. Curtin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

AB Dick Co

Original Assignee

Denis J. Curtin

A.B. Dick Company

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-08-28

Filing date

1975-08-15

Publication date

1980-01-01

1975-08-15 Application filed by Denis J. Curtin, A.B. Dick Company filed Critical Denis J. Curtin

1980-01-01 Application granted granted Critical

1980-01-01 Publication of CA1068970A publication Critical patent/CA1068970A/fr

Status Expired legal-status Critical Current

Links

-1 Alicyclic anhydride Chemical class 0.000 title claims abstract description 26
239000000203 mixture Substances 0.000 title claims abstract description 26
KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims abstract description 12
VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-UHFFFAOYSA-N 0.000 claims abstract description 10
239000007787 solid Substances 0.000 claims abstract description 9
238000000034 method Methods 0.000 claims abstract description 8
239000000758 substrate Substances 0.000 claims abstract description 8
230000014759 maintenance of location Effects 0.000 claims abstract description 4
238000000576 coating method Methods 0.000 claims description 32
239000011248 coating agent Substances 0.000 claims description 28
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
230000035945 sensitivity Effects 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
125000002723 alicyclic group Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
239000000463 material Substances 0.000 claims description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 8
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 4
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 4
FKNIDKXOANSRCS-UHFFFAOYSA-N 2,3,4-trinitrofluoren-1-one Chemical compound C1=CC=C2C3=C([N+](=O)[O-])C([N+]([O-])=O)=C([N+]([O-])=O)C(=O)C3=CC2=C1 FKNIDKXOANSRCS-UHFFFAOYSA-N 0.000 claims 2
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
239000003960 organic solvent Substances 0.000 claims 2
150000008064 anhydrides Chemical class 0.000 description 10
229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 6
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000000123 paper Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
229910052711 selenium Inorganic materials 0.000 description 4
239000011669 selenium Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
239000008199 coating composition Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
APQXWKHOGQFGTB-UHFFFAOYSA-N 1-ethenyl-9h-carbazole Chemical class C12=CC=CC=C2NC2=C1C=CC=C2C=C APQXWKHOGQFGTB-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
MQQRFOXFIPBFOV-UHFFFAOYSA-N 1,2-dimethylcyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1(C)C(C(O)=O)C(C(O)=O)C1(C)C(O)=O MQQRFOXFIPBFOV-UHFFFAOYSA-N 0.000 description 1
FGFOZLCWAHRUAJ-UHFFFAOYSA-N 2-nitrofluoren-1-one Chemical compound C1=CC=C2C3=CC=C([N+](=O)[O-])C(=O)C3=CC2=C1 FGFOZLCWAHRUAJ-UHFFFAOYSA-N 0.000 description 1
PWEKCCPUQNOPFO-UHFFFAOYSA-N 2-oxaspiro[3.3]heptane-1,3-dione Chemical class O=C1OC(=O)C11CCC1 PWEKCCPUQNOPFO-UHFFFAOYSA-N 0.000 description 1
LIBFVQBAZPYQCJ-UHFFFAOYSA-N 2-oxaspiro[3.4]octane-1,3-dione Chemical class O=C1OC(=O)C11CCCC1 LIBFVQBAZPYQCJ-UHFFFAOYSA-N 0.000 description 1
HHCHLHOEAKKCAB-UHFFFAOYSA-N 2-oxaspiro[3.5]nonane-1,3-dione Chemical class O=C1OC(=O)C11CCCCC1 HHCHLHOEAKKCAB-UHFFFAOYSA-N 0.000 description 1
NMNZZIMBGSGRPN-UHFFFAOYSA-N 3-oxabicyclo[3.2.0]heptane-2,4-dione Chemical compound O=C1OC(=O)C2CCC12 NMNZZIMBGSGRPN-UHFFFAOYSA-N 0.000 description 1
JOCHNIRUSHUAHQ-UHFFFAOYSA-N 3a-methyl-4,5,6,6a-tetrahydrocyclopenta[c]furan-1,3-dione Chemical compound C1CCC2C(=O)OC(=O)C21C JOCHNIRUSHUAHQ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010034960 Photophobia Diseases 0.000 description 1
229920002732 Polyanhydride Polymers 0.000 description 1
GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
238000007605 air drying Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052729 chemical element Inorganic materials 0.000 description 1
239000004020 conductor Substances 0.000 description 1
238000010276 construction Methods 0.000 description 1
QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 description 1
125000006159 dianhydride group Chemical group 0.000 description 1
239000002019 doping agent Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
208000013469 light sensitivity Diseases 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000011101 paper laminate Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1

Classifications

- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/001—Electric or magnetic imagery, e.g., xerography, electrography, magnetography, etc. Process, composition, or product
- Y10S430/10—Donor-acceptor complex photoconductor

Landscapes

Health & Medical Sciences (AREA)
Emergency Medicine (AREA)
Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Photoreceptors In Electrophotography (AREA)

CA233,538A 1974-08-28 1975-08-15 Utilisation d'un anhydride d'acide alicyclique dans un produit organique photoconducteur Expired CA1068970A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US501132A US3929478A (en)	1974-08-28	1974-08-28	Electrophotographic element which includes a photoconductive polyvinyl carbazole layer containing an alicyclic anhydride

Publications (1)

Publication Number	Publication Date
CA1068970A true CA1068970A (fr)	1980-01-01

Family

ID=23992258

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA233,538A Expired CA1068970A (fr)	1974-08-28	1975-08-15	Utilisation d'un anhydride d'acide alicyclique dans un produit organique photoconducteur

Country Status (5)

Country	Link
US (1)	US3929478A (fr)
JP (1)	JPS5177240A (fr)
CA (1)	CA1068970A (fr)
DE (1)	DE2537770A1 (fr)
GB (1)	GB1479399A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4013464A (en) *	1975-12-03	1977-03-22	Eastman Kodak Company	Photoconductive and radioconductive compositions and elements containing tetragonal lead monoxide
JPS57132157A (en) *	1981-02-09	1982-08-16	Mita Ind Co Ltd	Sensitized composition of electrophotographic photosensitizer
JPS57165839A (en) *	1981-04-06	1982-10-13	Mita Ind Co Ltd	Electrophotographic sensitive agent composition

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3484237A (en) *	1966-06-13	1969-12-16	Ibm	Organic photoconductive compositions and their use in electrophotographic processes
US3764311A (en) *	1966-09-01	1973-10-09	Xerox Corp	Frost imaging system
GB1248744A (en) *	1967-11-01	1971-10-06	Xerox Corp	Migration colour imaging
US3849130A (en) *	1972-03-20	1974-11-19	Pitney Bowes Inc	Organic photoconductive composition and electrophotographic member

1974
- 1974-08-28 US US501132A patent/US3929478A/en not_active Expired - Lifetime
1975
- 1975-08-15 CA CA233,538A patent/CA1068970A/fr not_active Expired
- 1975-08-25 DE DE19752537770 patent/DE2537770A1/de not_active Withdrawn
- 1975-08-27 GB GB35420/75A patent/GB1479399A/en not_active Expired
- 1975-08-28 JP JP50103551A patent/JPS5177240A/ja active Pending

Also Published As

Publication number	Publication date
JPS5177240A (en)	1976-07-05
GB1479399A (en)	1977-07-13
US3929478A (en)	1975-12-30
DE2537770A1 (de)	1976-03-11

Legal Events

Date	Code	Title	Description
1997-01-01	MKEX	Expiry

Publication	Publication Date	Title
IL28067A (en)	1971-06-23	Organic photoconductive compositions
US3421891A (en)	1969-01-14	Electrophotographic materials comprising brominated poly-n-vinyl carbazoles
US4184871A (en)	1980-01-22	Photosensitive composition for electrophotography
US3418116A (en)	1968-12-24	Electrophotographic materials comprising polymeric intramolecular charge transfer complexes
US3624226A (en)	1971-11-30	Electrographic organic photoconductor comprising of n,n,n{40 ,n{40 , tetrabenzyl 4,4{40 oxydianaline
US3257202A (en)	1966-06-21	Electrophotographic material and process
JPH05107784A (ja)	1993-04-30	電子写真感光体
CA1068970A (fr)	1980-01-01	Utilisation d'un anhydride d'acide alicyclique dans un produit organique photoconducteur
US3764315A (en)	1973-10-09	Ambipolar electrophotographic plate
US3072479A (en)	1963-01-08	Electrophotographic plates comprising solid solutions of oxazolones
US3652269A (en)	1972-03-28	Photoconductive elements containing halogenated polyethylene binders
US3871883A (en)	1975-03-18	Electrophotographic photoconductive layer comprising an organic photoconductor and a dicyanomethylene-indenothiophene sensitizer
US3791824A (en)	1974-02-12	Conjugated polymers in electrophotography
US3867140A (en)	1975-02-18	Organic photoconductor-(mononitro-2-aza-fluorenylidene)malononitrile charge transfer complex
US3770428A (en)	1973-11-06	PHOTOCONDUCTIVE REACTION PRODUCT OF N -beta- CHLORETHYL CARBAZOLE AND FORMALDEHYDE
US3674473A (en)	1972-07-04	Cumulene containing photoconductive binder elements for use in electrophotography
US3884690A (en)	1975-05-20	Polyester photoconductors and matrix materials
CA1048841A (fr)	1979-02-20	Photoconducteur elctrophotographique organique
JPH0331849A (ja)	1991-02-12	電子写真記録材料
US3607257A (en)	1971-09-21	Photoconductive compositions and elements
US3841871A (en)	1974-10-15	Cumulene-resin binder photoconductive elements
US3240594A (en)	1966-03-15	Electrophotographic material
GB2129149A (en)	1984-05-10	Electrophotographic photoconductors
US4160667A (en)	1979-07-10	Aluminum chelates as acceptor type sensitizers and plasticizers for photoconductive polymers
JPH02282262A (ja)	1990-11-19	電子写真感光体