CA1068970A - Alicyclic anhydride in organic photoconductive composition - Google Patents
Alicyclic anhydride in organic photoconductive compositionInfo
- Publication number
- CA1068970A CA1068970A CA233,538A CA233538A CA1068970A CA 1068970 A CA1068970 A CA 1068970A CA 233538 A CA233538 A CA 233538A CA 1068970 A CA1068970 A CA 1068970A
- Authority
- CA
- Canada
- Prior art keywords
- alicyclic
- composition
- coating
- anhydride
- photoconductive
- Prior art date
- 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
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)
Abstract
ABSTRACT OF THE DISCLOSURE
For use in an electrophotographic copy process, a photoconductive element formed of an organic photoconductive composition on a suitable substrate, in which the speed and charge retention of the organic photoconductor, preferably a polymerized vinyl carbazole and 2,4,7-trinitro-9-fluorenone, is improved by the presence of an alicyclic anhydride in an amount within the range of 0.01% to 1.0% by weight of the coated solids.
For use in an electrophotographic copy process, a photoconductive element formed of an organic photoconductive composition on a suitable substrate, in which the speed and charge retention of the organic photoconductor, preferably a polymerized vinyl carbazole and 2,4,7-trinitro-9-fluorenone, is improved by the presence of an alicyclic anhydride in an amount within the range of 0.01% to 1.0% by weight of the coated solids.
Description
~8~70 This invention relates to photoconductors and more particularly to an organic photoconductor composition for use in the preparation of photoconductive elements in the produc-tion of copy by the electrophotographic process.
In the electrophoto~raphic copy process, use is made of a photoconductive surface onto which a uniform electrostat- ;~
ic charge is applied. The charge is retained on the surface except for those areas that are rendered conductive during ex~
posure to a light pattern, leaving a latent electrostatic im-age on the non-exposed portions of the photoconductive surface. ~-~
The latent electrostatic image is subsequently developed in a conventional manner, as by means of a dry developing powder which is cascaded o~er the surface, or by a liquid developer or toner suspended in an insulating liquid with which the plate surface is wet. In~tead, the latent electrostatic image can be transferred to a copy sheet for development of the image there-on, as by a liquid or powder developer. - ;`~
.: . .. .
To the present, especially in relatively high speed copy machines, amorphous selenium, with or without an added dopant, has been used to provide the photoconductive surface ; on a suitable support. While selenium provides a photocon-ductive surface having the desired speed and sensitivity for use in high speed copy machines, selenium represents a rela-tively expensive material which is difficult to apply, and its use as a photoconductive composition is somewhat restricted to a support ~ormed of a rigid material such as a metal drum or plate.
There is considerable interest in a low cost organic photoconductive composition which might be applied by conven-tional coating techniques, for use on various supports, such .. ,; , .
~ :
9~ ~
,... .
as on an endless belt, flexible paper, metal or plastic strip, and the like, as well as on a rigid metal drum or plate.
While organic photoconductors offer advantages of the type described, they are also faced with a number of dis-advantages in that organic photoconductors, which have been -suggested to the present, are characterized by low charge acceptance and lesser sensitivity by comparison with selenium.
In U.S. Patent No. 3,484,237, description is made of an organic photoconductor composition formed of a polymerized vinyl carbazole compound to which 2,4,7-trinitro-9-fluorenone has been added as an electron acceptor to lower the dark conductivity of the photoconductive layer and to increase the sensitivity in the visible range.
Organic photoconductors of the type described are capable of copy speeds in the range of 10 to 25 copies per minute.
It is, of course, desirable to increase the copy speed ~ , .
~,? of organic photoconductors to a rate considerably in excess of 25 copies per minute. This can be accomplished by increase in the charge acceptance of the photoconductor as well as in the photoconductivity or light sensitivity of the photoconductor, as measured by light decay sensitivity of the charge on the photoconductive surface, as the result of light exposure.
; It has been found, in accordance with the practice of this invention, that the charge acceptance and sensitivity of organic photoconductors can be markedly increased when the ;
i i~
organic photoconductor is formulated to contain an alicyclic anhydride. ~;
The present invention therefore provides in an 3a electrophotographic element for use in an electrophotographic ~ ~,o~j~397~ ~
copy process formed of a substrate having on one surface an .
organic photoconductive coating formed of 2, 4, 7-trinitro-9-fluorenone and a polymerized vinyl carbazole, the improvement :
wherein a saturated alicyclic anhydride having from 3 to 20 carbon atoms in the ring is incorporated into the organic photo-conductive composition in an amount within the range of 0.01% to 1.0% by weight of the coating solids, whereby the charge reten- ~;
tion and sensitivity of the photoconductive coating is markedly improved to increase copy speed.
The present invention also provides an organic photo-conductive composition for use in the preparation of the electro- :~
photographic element as above in which the composition consists r essentially of 2, 4, 7-trinitro-9-fluorenone, polymerized vinyl . .
carbazole in the ratio of about 0.49 to 1.23 moles of the tri-.. nitro fluorenone per monomeric unit of the polymerized vinyl ... carbazole and 0.01% to 1.0% by weight (based on coating solids~ -:
of a saturated alicyclic anhydride having from 3 to 20 carbon atoms in the alicyclic group.
The improvement in charge acceptance and sensitivity, as measured by charge decay, is particularly significant ,;
~.
~ 2a-:
:::
68~
when the alicyclic anhydride is present in an organic photo-conductor composition formulated of a polymerized vinyl car-bazole (PVK) in 2,4,7-trinitro-9-fluorenone (T~F), to form photoconductive coatings of the charge-transfer complex types.
As the alicyclic anhydride, it is preferred to make use of one or more of the following:
a) Cyclobutanedicarboxvlic anhydrides R3 ~ ~_ _ _ ~ C
R4'~ 0 .. } .. ,~
wherein Rl_6 are hydrogen, lower alkyl groups, such as methyl, r ethyl, propyl, etc., halogen such as chlorine, bromine and iodine, hydroxy or nitr~ groups. Rl_6 can be the same or different. R2 a~d R4 can also be an anhydride functional ~ group. Representative of such anhydrides are such compounds i as 1,2-cyclobutanedicarboxylic anhydride, including the cis and trans isomers thereof, 1,2,3,4-cyclobutanetetracarboxylic-1,2,3,4-dianhydride, 1,2,3,4-tetramethyl-1,2-cyclobutanedi~
carboxylic anhydride, 3-chl~ro-3-methyl-1,2-cyclobutanedi-carboxylic anhydride, and 1,4-dimethyl-1,2,3,4-cyclobutane-tetracarboxylic dianhydride.
b) Cyclopentanedicarboxylic anhYdrides -~
R4 ~ ~ ~ Rl R6 - 1 -- -~ ~ ' ~' R7 ! ~ ;
........ .. .. ... ....
:`
0 ~
: `
where R1_8 are hydrogen, lower alkyl groups such as methyl, ethyl, propyl, butyl, etc., halogen such as chlorine, bromine, iodine, hydroxy or nitro, in which Rl_8 can be the same or different. R2 and R4 can also be an anhydride functional group. Representative of such cyclopentanedicarboxylic anhy-drides are l,2~cyclopentanedicarboxylic anhydride, 3,3-di-methyl-1,2-cyclopentanedicarboxylic anhydride, 4,5-dihydroxy-1,2-cyclopentanedicarboxylic anhydride, 1-methyl-1,2-cyclo-pentanedicarboxylic anhydride, cis, cls, cis, cis-1,2,3,4' 10 cyclopentanetetracarboxylic dianhydride. ~;
c) CYclohexanedicarboxYlic anhvdrides R~R2 ~ ~ , R ~ 0 R7 ~ 10 R8 Rg where Rl_lo can be hydrogen, lower alkyl groups such as methyl, ethyl, propyl, etc., halogen such as chlorine, bromine, iodine, etcO, hydroxy, nitrile or nitro ~roups. Rl_lo can be the same or different and R2 and R4 as well as R6 and R8 can be an an~
~ydride functional group. Representative of such cyclohexane-dicarboxylic anhydrides are l,2-cyclohexanedicarboxylic anhy-dride, and their cls and trans isomers, cis-1,2-dimethyl-1,2-cyclohexanedicarboxylic anhydride, trans-1,2-dimethyl-1,2-cyclohexanedicarboxylic anhydride, 1,2,4,S-cyclohexanetetra-carboxylic-1,2,4,5-dianhydride, and 1,2,3~4,5,6-cyclohexane-hexacarboxylic 1~2;3~4U5~6-trianhydride.
Suitable alicyclic anhydrides range from an~ydrides 3 having at least 3 carbon atoms in the alicyclic group as ~-- , .
97~ ~:
represented by l,2-cyclopropanedicarboxylic anhydride, to and including anhydrides, dianhydrides and polyanhydrides having up to 18-20 carbon atoms in the cyclic group, although it is preferred to make use of anhydrides having substituents as described in a, b and c above, in which the number o~ carbon atoms in the alicyclic group are within the range of 4-10, as represented by the foregoin~ as well as a l,2-cycloheptanedi-carboxylic anhydride and l,2-cyclodecanedicarboxylic anhydride.
Noticeable improvement is observed when the alicyclic anhydride is employed in the photoconductive composition in an amount of at least 0.01% by weight of the coating solids to as much as 1.0% by wei~ht of the coating solids, but it is pre-ferred to make use of an amount within the range of 0.02% to 0.5% by weight of the~botal ~umeof PVK and TNFo The following represent the polymerized vinyl carba-zole compounds which may be used in the formulation of the or-ganic photoconductive coatings of this invention, namely:
poly-N-vinyl carbazole and polyvinyl-N-lowar alkyl carbazoles of the type described in the U. S. patent No. 3,484,237. The ; 20 following can be given by way of examples of suitable poly-N-lower alkyl carbazoles, namely, poly-2-vinyl-N-methylcarbazole, poly-3-vinyl-N-ethylcarbazole, poly-2-vinyl-N-ethylcarbazole~
poly-3-vinyl-N-methylcarbazole, poly-3-vinyl-N-isopropylcarba-zole, poly-2-vinyl-N-butylcarbazole, poly-3-vinyl-~-butyl-carbazole, poly-2-vinyl-N-pentylcarbazole, poly-3-vinyl-N-pentylcarbazole, poly-2-vinyl-N~hexylcarbazolet poly-3-vinyl- -N-hexylcarbazole, poly-2-vinyl-N-heptylcarbazole, and poly-3-vinyl-N-heptylcarbazole. Mixtures and copol~mers of the poly-merized vinyl-carbazole compounds also may be used.
~06~
When the organic photoconductor is of the charge-transfer type -formulated of polymerized vinyl carbazoles and
In the electrophoto~raphic copy process, use is made of a photoconductive surface onto which a uniform electrostat- ;~
ic charge is applied. The charge is retained on the surface except for those areas that are rendered conductive during ex~
posure to a light pattern, leaving a latent electrostatic im-age on the non-exposed portions of the photoconductive surface. ~-~
The latent electrostatic image is subsequently developed in a conventional manner, as by means of a dry developing powder which is cascaded o~er the surface, or by a liquid developer or toner suspended in an insulating liquid with which the plate surface is wet. In~tead, the latent electrostatic image can be transferred to a copy sheet for development of the image there-on, as by a liquid or powder developer. - ;`~
.: . .. .
To the present, especially in relatively high speed copy machines, amorphous selenium, with or without an added dopant, has been used to provide the photoconductive surface ; on a suitable support. While selenium provides a photocon-ductive surface having the desired speed and sensitivity for use in high speed copy machines, selenium represents a rela-tively expensive material which is difficult to apply, and its use as a photoconductive composition is somewhat restricted to a support ~ormed of a rigid material such as a metal drum or plate.
There is considerable interest in a low cost organic photoconductive composition which might be applied by conven-tional coating techniques, for use on various supports, such .. ,; , .
~ :
9~ ~
,... .
as on an endless belt, flexible paper, metal or plastic strip, and the like, as well as on a rigid metal drum or plate.
While organic photoconductors offer advantages of the type described, they are also faced with a number of dis-advantages in that organic photoconductors, which have been -suggested to the present, are characterized by low charge acceptance and lesser sensitivity by comparison with selenium.
In U.S. Patent No. 3,484,237, description is made of an organic photoconductor composition formed of a polymerized vinyl carbazole compound to which 2,4,7-trinitro-9-fluorenone has been added as an electron acceptor to lower the dark conductivity of the photoconductive layer and to increase the sensitivity in the visible range.
Organic photoconductors of the type described are capable of copy speeds in the range of 10 to 25 copies per minute.
It is, of course, desirable to increase the copy speed ~ , .
~,? of organic photoconductors to a rate considerably in excess of 25 copies per minute. This can be accomplished by increase in the charge acceptance of the photoconductor as well as in the photoconductivity or light sensitivity of the photoconductor, as measured by light decay sensitivity of the charge on the photoconductive surface, as the result of light exposure.
; It has been found, in accordance with the practice of this invention, that the charge acceptance and sensitivity of organic photoconductors can be markedly increased when the ;
i i~
organic photoconductor is formulated to contain an alicyclic anhydride. ~;
The present invention therefore provides in an 3a electrophotographic element for use in an electrophotographic ~ ~,o~j~397~ ~
copy process formed of a substrate having on one surface an .
organic photoconductive coating formed of 2, 4, 7-trinitro-9-fluorenone and a polymerized vinyl carbazole, the improvement :
wherein a saturated alicyclic anhydride having from 3 to 20 carbon atoms in the ring is incorporated into the organic photo-conductive composition in an amount within the range of 0.01% to 1.0% by weight of the coating solids, whereby the charge reten- ~;
tion and sensitivity of the photoconductive coating is markedly improved to increase copy speed.
The present invention also provides an organic photo-conductive composition for use in the preparation of the electro- :~
photographic element as above in which the composition consists r essentially of 2, 4, 7-trinitro-9-fluorenone, polymerized vinyl . .
carbazole in the ratio of about 0.49 to 1.23 moles of the tri-.. nitro fluorenone per monomeric unit of the polymerized vinyl ... carbazole and 0.01% to 1.0% by weight (based on coating solids~ -:
of a saturated alicyclic anhydride having from 3 to 20 carbon atoms in the alicyclic group.
The improvement in charge acceptance and sensitivity, as measured by charge decay, is particularly significant ,;
~.
~ 2a-:
:::
68~
when the alicyclic anhydride is present in an organic photo-conductor composition formulated of a polymerized vinyl car-bazole (PVK) in 2,4,7-trinitro-9-fluorenone (T~F), to form photoconductive coatings of the charge-transfer complex types.
As the alicyclic anhydride, it is preferred to make use of one or more of the following:
a) Cyclobutanedicarboxvlic anhydrides R3 ~ ~_ _ _ ~ C
R4'~ 0 .. } .. ,~
wherein Rl_6 are hydrogen, lower alkyl groups, such as methyl, r ethyl, propyl, etc., halogen such as chlorine, bromine and iodine, hydroxy or nitr~ groups. Rl_6 can be the same or different. R2 a~d R4 can also be an anhydride functional ~ group. Representative of such anhydrides are such compounds i as 1,2-cyclobutanedicarboxylic anhydride, including the cis and trans isomers thereof, 1,2,3,4-cyclobutanetetracarboxylic-1,2,3,4-dianhydride, 1,2,3,4-tetramethyl-1,2-cyclobutanedi~
carboxylic anhydride, 3-chl~ro-3-methyl-1,2-cyclobutanedi-carboxylic anhydride, and 1,4-dimethyl-1,2,3,4-cyclobutane-tetracarboxylic dianhydride.
b) Cyclopentanedicarboxylic anhYdrides -~
R4 ~ ~ ~ Rl R6 - 1 -- -~ ~ ' ~' R7 ! ~ ;
........ .. .. ... ....
:`
0 ~
: `
where R1_8 are hydrogen, lower alkyl groups such as methyl, ethyl, propyl, butyl, etc., halogen such as chlorine, bromine, iodine, hydroxy or nitro, in which Rl_8 can be the same or different. R2 and R4 can also be an anhydride functional group. Representative of such cyclopentanedicarboxylic anhy-drides are l,2~cyclopentanedicarboxylic anhydride, 3,3-di-methyl-1,2-cyclopentanedicarboxylic anhydride, 4,5-dihydroxy-1,2-cyclopentanedicarboxylic anhydride, 1-methyl-1,2-cyclo-pentanedicarboxylic anhydride, cis, cls, cis, cis-1,2,3,4' 10 cyclopentanetetracarboxylic dianhydride. ~;
c) CYclohexanedicarboxYlic anhvdrides R~R2 ~ ~ , R ~ 0 R7 ~ 10 R8 Rg where Rl_lo can be hydrogen, lower alkyl groups such as methyl, ethyl, propyl, etc., halogen such as chlorine, bromine, iodine, etcO, hydroxy, nitrile or nitro ~roups. Rl_lo can be the same or different and R2 and R4 as well as R6 and R8 can be an an~
~ydride functional group. Representative of such cyclohexane-dicarboxylic anhydrides are l,2-cyclohexanedicarboxylic anhy-dride, and their cls and trans isomers, cis-1,2-dimethyl-1,2-cyclohexanedicarboxylic anhydride, trans-1,2-dimethyl-1,2-cyclohexanedicarboxylic anhydride, 1,2,4,S-cyclohexanetetra-carboxylic-1,2,4,5-dianhydride, and 1,2,3~4,5,6-cyclohexane-hexacarboxylic 1~2;3~4U5~6-trianhydride.
Suitable alicyclic anhydrides range from an~ydrides 3 having at least 3 carbon atoms in the alicyclic group as ~-- , .
97~ ~:
represented by l,2-cyclopropanedicarboxylic anhydride, to and including anhydrides, dianhydrides and polyanhydrides having up to 18-20 carbon atoms in the cyclic group, although it is preferred to make use of anhydrides having substituents as described in a, b and c above, in which the number o~ carbon atoms in the alicyclic group are within the range of 4-10, as represented by the foregoin~ as well as a l,2-cycloheptanedi-carboxylic anhydride and l,2-cyclodecanedicarboxylic anhydride.
Noticeable improvement is observed when the alicyclic anhydride is employed in the photoconductive composition in an amount of at least 0.01% by weight of the coating solids to as much as 1.0% by wei~ht of the coating solids, but it is pre-ferred to make use of an amount within the range of 0.02% to 0.5% by weight of the~botal ~umeof PVK and TNFo The following represent the polymerized vinyl carba-zole compounds which may be used in the formulation of the or-ganic photoconductive coatings of this invention, namely:
poly-N-vinyl carbazole and polyvinyl-N-lowar alkyl carbazoles of the type described in the U. S. patent No. 3,484,237. The ; 20 following can be given by way of examples of suitable poly-N-lower alkyl carbazoles, namely, poly-2-vinyl-N-methylcarbazole, poly-3-vinyl-N-ethylcarbazole, poly-2-vinyl-N-ethylcarbazole~
poly-3-vinyl-N-methylcarbazole, poly-3-vinyl-N-isopropylcarba-zole, poly-2-vinyl-N-butylcarbazole, poly-3-vinyl-~-butyl-carbazole, poly-2-vinyl-N-pentylcarbazole, poly-3-vinyl-N-pentylcarbazole, poly-2-vinyl-N~hexylcarbazolet poly-3-vinyl- -N-hexylcarbazole, poly-2-vinyl-N-heptylcarbazole, and poly-3-vinyl-N-heptylcarbazole. Mixtures and copol~mers of the poly-merized vinyl-carbazole compounds also may be used.
~06~
When the organic photoconductor is of the charge-transfer type -formulated of polymerized vinyl carbazoles and
2,4,7-krinitro-9-fluorenone, the ingredients are formulated into the coating composition in the ratio of about 0.49 to 1.23 moles of TNF per monomer unit of PVK, which ratio will continue in the organic photoconductor that is formed upon coating a suitable substrate and then dried to cure the coating onto the substrate.
As the substrate, use can be made of a rigid plate ~ .
or drum formed of glass or of a metal such as aluminum having a silicated surface and the like, or the substrate upon which the photoconductive coating is applied may be a flexible element, such as a plate, drum, or endless kelt formed of paper, plastic, i-metal-paper laminate, or a sheet of silicated aluminum or the like.
The materials are formulated into a composition for coating onto a suitable substrate by first dissolving the poly-vinylcarbazole component in a suitable solvent, such as tetra-hydrofuran, and then admixing the solution of the polyvinyl-carbazole with the 2,4,7-trinitro-9-fluorenone and alicyclic anhydride, preferably in solution in the same solvent, and any additional solvent required to achieve the desired consistency for the coating composition. The materials may be worked into solution on a roller mill and the like and coated onto the sub- ;~
strate by conventional coating means, followed by air drying and then curing at elevated temperature such as for one hour at 50-60C to provide coatings having a thickness within the range of 5-30 ~ and preferably 8-15~ Instead of tetrahydrofuran, other ;
solvents such as 1,2-dichloroethane and chlorobenzene may be used.
The photoconductive compositions of the present inven-tion are useful in the conventional zerographic process in --r-~ -6~
, . ! ., .
which an electrostatic image is formed on the surface of the photoconductive element and the electrostatic image is sub-sequently developed. In practice, the photoconductive element is electrostatically charged and exposed to a pattern of light and dark to form an electrostatic image. Thereafter, the electrostatic image can either be developed with a convention-al electroscopic powder developer on the photoconductive ele-ment and the devçloped image transferred to plain paper, or the electrostatic image can be transferred to a dielectric paper for development with an electroscopic developer (powder ~ -or liquid).
The following examples are given by way of illus- ~
tration, but not by way of limitation, of the practice of the `
invention:
In this example, comparison is made between an or-ganic photoconductor embodying the features of this invention, with a photoconductor of identical composition except for the -`
omission of the alicyclic acid anhydride component.
For this purpose, a mi~ture was prepared of the -;
following ingredients:
24.8 grams 2,4,7-trinitro-9-fluorenone 200 ml tetrahydrofuran (previously dried ovPr sodium) 1~0 ml poly-N-vinylcarbazole in 10% solution in tetrahydro~uran Solution was effected by roller milling until dis-solved~ The batch was divided into two equal segments, here-inafter idantified as l(a) and l~b).
Each segment was diluted with equal volumes of tetrahydrofuran to reduce the materials to coatin~ viscosity.
1~8970 2 ml of a 1% solution of cis~l,2-cyclobutanedicarboxylic acid anhydride in tetrahydrofuran was added to segment l(b).
The coating compositions were applied onto separate silicated aluminum belts having a thickness of 3.5 mils. Coat-ing was effected by mounting the belts on a drum operated forrotational movement about a horizontal axis. Application was made by means of an air brush mounted a fixed distance from the surface o~ the belt and displaced crosswise over the sur~
face of the belt in increments of 2 mm per revolution, and operated under a pressure of 18 psi with nitrogen. An amount was applied to form a dried coating having a thickness of about 10-12 microns.
The coated plates were allow~d to air dry and then they were cured for one hour at 50C.
The plates were each tested for charge acceptance and charge retention by exposing the plates to negative elec-trostatic corona charge of 6 kv by passing the plates beneath charging wires. Charge acceptance and charge retention were measured by a Monroe electrometer which measures the charge on the surfaces of the plates in volts.
The plates were also each tested for sensitivity by the use o~ the Monroe electrometer to measure the amount of charge dissipated by light exposure. For this purpose, exposure was made with a tungsten photo-enlarger lamp of 150 watts operating through an enlarger~ Energy of exposure iden~
tifies the amount of light 'chat ~ell on the plate in ~ J/cm2, as measured by a Hewlett-Packard radiant ~lux meter.
The following values wer~ obtained with the plates of Examples l(a) and 1 (b): ~-~8-7~3 '-~
Example Charge acceptance Sensitivity in volts in Vcm2/ L~
1 (a) 130 3.0 1 (b) 650 18.7 The sensitivity values given above were for the average of exposures at 7, 14 and 28 ~/cm2.
It will be apparent from the above that the addition of the alicyclic acid anhydride gave an improvement of 500~/0 .
in charge acceptance and 623% in sensitivity.
Plates prepared or a composition corresponding to ` 3 Example l(b) gave a dark decay rate of 3.0 volts per second.
The amount of conductive coating applied to the sub- ~
strate is not significant. The desired results can ~e obtained ` -in coating weights sufficient to provide coating thickness of ; 15 5 microns; however, it is undesirable from the standpoint o economics and flexibility of the coating to exceed a coating thickness of about 30 microns. In the preferred practice of this invention, use is made of the organic photoconductor in `
dry coatings having a thickness within the range of 8 to 15 :
microns.
With plates embodying the features of this invention, copies have been produced by the electrostatic technique at ;- -~
copy speeds considerab-y greater than 25 copies per minute and up to as many as 60 copies per minute.
The terms "carboxylic acid anhydride" and "carboxyl-ic anhydride" are used by the skilled in -the art and in this application to identify the same compound.
It will be und~rs-tood that changes may be made in the details of formulation, construction and operation with-out departing fr~m the spirit of the invention, especially as de~ined in the following claims.
_g_
As the substrate, use can be made of a rigid plate ~ .
or drum formed of glass or of a metal such as aluminum having a silicated surface and the like, or the substrate upon which the photoconductive coating is applied may be a flexible element, such as a plate, drum, or endless kelt formed of paper, plastic, i-metal-paper laminate, or a sheet of silicated aluminum or the like.
The materials are formulated into a composition for coating onto a suitable substrate by first dissolving the poly-vinylcarbazole component in a suitable solvent, such as tetra-hydrofuran, and then admixing the solution of the polyvinyl-carbazole with the 2,4,7-trinitro-9-fluorenone and alicyclic anhydride, preferably in solution in the same solvent, and any additional solvent required to achieve the desired consistency for the coating composition. The materials may be worked into solution on a roller mill and the like and coated onto the sub- ;~
strate by conventional coating means, followed by air drying and then curing at elevated temperature such as for one hour at 50-60C to provide coatings having a thickness within the range of 5-30 ~ and preferably 8-15~ Instead of tetrahydrofuran, other ;
solvents such as 1,2-dichloroethane and chlorobenzene may be used.
The photoconductive compositions of the present inven-tion are useful in the conventional zerographic process in --r-~ -6~
, . ! ., .
which an electrostatic image is formed on the surface of the photoconductive element and the electrostatic image is sub-sequently developed. In practice, the photoconductive element is electrostatically charged and exposed to a pattern of light and dark to form an electrostatic image. Thereafter, the electrostatic image can either be developed with a convention-al electroscopic powder developer on the photoconductive ele-ment and the devçloped image transferred to plain paper, or the electrostatic image can be transferred to a dielectric paper for development with an electroscopic developer (powder ~ -or liquid).
The following examples are given by way of illus- ~
tration, but not by way of limitation, of the practice of the `
invention:
In this example, comparison is made between an or-ganic photoconductor embodying the features of this invention, with a photoconductor of identical composition except for the -`
omission of the alicyclic acid anhydride component.
For this purpose, a mi~ture was prepared of the -;
following ingredients:
24.8 grams 2,4,7-trinitro-9-fluorenone 200 ml tetrahydrofuran (previously dried ovPr sodium) 1~0 ml poly-N-vinylcarbazole in 10% solution in tetrahydro~uran Solution was effected by roller milling until dis-solved~ The batch was divided into two equal segments, here-inafter idantified as l(a) and l~b).
Each segment was diluted with equal volumes of tetrahydrofuran to reduce the materials to coatin~ viscosity.
1~8970 2 ml of a 1% solution of cis~l,2-cyclobutanedicarboxylic acid anhydride in tetrahydrofuran was added to segment l(b).
The coating compositions were applied onto separate silicated aluminum belts having a thickness of 3.5 mils. Coat-ing was effected by mounting the belts on a drum operated forrotational movement about a horizontal axis. Application was made by means of an air brush mounted a fixed distance from the surface o~ the belt and displaced crosswise over the sur~
face of the belt in increments of 2 mm per revolution, and operated under a pressure of 18 psi with nitrogen. An amount was applied to form a dried coating having a thickness of about 10-12 microns.
The coated plates were allow~d to air dry and then they were cured for one hour at 50C.
The plates were each tested for charge acceptance and charge retention by exposing the plates to negative elec-trostatic corona charge of 6 kv by passing the plates beneath charging wires. Charge acceptance and charge retention were measured by a Monroe electrometer which measures the charge on the surfaces of the plates in volts.
The plates were also each tested for sensitivity by the use o~ the Monroe electrometer to measure the amount of charge dissipated by light exposure. For this purpose, exposure was made with a tungsten photo-enlarger lamp of 150 watts operating through an enlarger~ Energy of exposure iden~
tifies the amount of light 'chat ~ell on the plate in ~ J/cm2, as measured by a Hewlett-Packard radiant ~lux meter.
The following values wer~ obtained with the plates of Examples l(a) and 1 (b): ~-~8-7~3 '-~
Example Charge acceptance Sensitivity in volts in Vcm2/ L~
1 (a) 130 3.0 1 (b) 650 18.7 The sensitivity values given above were for the average of exposures at 7, 14 and 28 ~/cm2.
It will be apparent from the above that the addition of the alicyclic acid anhydride gave an improvement of 500~/0 .
in charge acceptance and 623% in sensitivity.
Plates prepared or a composition corresponding to ` 3 Example l(b) gave a dark decay rate of 3.0 volts per second.
The amount of conductive coating applied to the sub- ~
strate is not significant. The desired results can ~e obtained ` -in coating weights sufficient to provide coating thickness of ; 15 5 microns; however, it is undesirable from the standpoint o economics and flexibility of the coating to exceed a coating thickness of about 30 microns. In the preferred practice of this invention, use is made of the organic photoconductor in `
dry coatings having a thickness within the range of 8 to 15 :
microns.
With plates embodying the features of this invention, copies have been produced by the electrostatic technique at ;- -~
copy speeds considerab-y greater than 25 copies per minute and up to as many as 60 copies per minute.
The terms "carboxylic acid anhydride" and "carboxyl-ic anhydride" are used by the skilled in -the art and in this application to identify the same compound.
It will be und~rs-tood that changes may be made in the details of formulation, construction and operation with-out departing fr~m the spirit of the invention, especially as de~ined in the following claims.
_g_
Claims (14)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. In an electrophotographic element for use in an electrophotographic copy process formed of a substrate having on one surface an organic photoconductive coating formed of 2, 4, 7-trinitro-9-fluorenone and a polymerized vinyl carbazole, the improvement wherein a saturated alicyclic anhydride having from 3 to 20 carbon atoms in the ring is incorporated into the organic photoconductive composition in an amount within the range of 0.01% to 1.0% by weight of the coating solids, whereby the charge retention and sensitivity of the photoconductive coating is markedly improved to increase copy speed.
2. An electrophotographic element as claimed in claim 1 in which the organic photoconductive coating comprises 2, 4, 7-trinitro-9-fluorenone and a polymerized vinyl carbazole present in the ratio of 0.49 to 1.23 moles of the trinitro fluorenone per monomeric unit of polymerized vinyl carbazole.
3. An electrophotographic element as claimed in claim 2 in which the alicyclic anhydride is present in the coating in an amount within the range of 0.02% to 0.5% by weight of the coating solids.
4. An electrophotographic element as claimed in claim 1, 2 or 3 in which the photoconductive coating is of a thickness within the range of 5-30 microns.
5. An electrophotographic element as claimed in claim 1, 2 or 3 in which the photoconductive coating is of a thickness within the range of 8-15 microns.
6. An electrophotographic element as claimed in claim 2 in which the polymerized vinyl carbazole is poly-N-vinyl carba-zole.
7. An electrophotographic element as claimed in claim 1 in which the cyclic group of the alicyclic anhydride is selected from the group consisting of cyclobutane, cyclopentane and cyclohexane, which are unsubstituted or substituted by at least one of lower alkyl, chlorine, bromine, iodine, hydroxy, and nitro radicals.
8. An organic photoconductive composition for use in the preparation of the electrophotographic element claimed in claim 1 in which the composition consists essentially of 2, 4, 7-trinitro-9-fluorenone, polymerized vinyl carbazole in the ratio of about 0.49 to 1.23 moles of the trinitro fluorenone per monomeric unit of the polymerized vinyl carbazole and 0.01% to 1.0% by weight (based on coating solids) of a saturated alicyclic anhydride having from 3 to 20 carbon atoms in the alicyclic group.
9. A composition as claimed in claim 8 in which the materials are present in solution in an organic solvent.
10. A composition as claimed in claim 9 in which the alicyclic anhydride is present in an amount within the range of 0.02% to 0.5% by weight of the coated solids.
11. A composition as claimed in claim 9 in which the organic solvent in which the photoconductive materials are dissolved is tetrahydrofuran.
12. A composition as claimed in claim 8 in which the alicyclic group of the alicyclic anhydride is selected from the group consisting of cyclobutane, cyclopentane and cyclohexane, which are unsubstituted or substituted by at least one of lower alkyl, chlorine, bromine, iodine, hydroxy, and nitro radicals.
13. An electrophotographic element according to claim 2, 3 or 6 wherein in the alicyclic group of the alicyclic anhydride is selected from cyclobutane, cyclopentane and cyclohexane which are unsubstituted or substituted by at least one of lower alkyl, chlorine, bromine, iodine, hydroxy, and nitro radicals.
14. A composition according to claim 8, 9 or 10 wherein in the alicyclic group of the alicyclic anhydride is selected from cyclobutane, cyclopentane and cyclohexane which are unsubstituted or substituted by at least one of lower alkyl, chlorine, bromine, iodine, hydroxy, and nitro radicals.
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 (en) | 1980-01-01 |
Family
ID=23992258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA233,538A Expired CA1068970A (en) | 1974-08-28 | 1975-08-15 | Alicyclic anhydride in organic photoconductive composition |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3929478A (en) |
| JP (1) | JPS5177240A (en) |
| CA (1) | CA1068970A (en) |
| DE (1) | DE2537770A1 (en) |
| GB (1) | GB1479399A (en) |
Families Citing this family (3)
| 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)
| 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 |
| FR1587252A (en) * | 1967-11-01 | 1970-03-13 | ||
| 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/en not_active Expired
- 1975-08-25 DE DE19752537770 patent/DE2537770A1/en not_active Withdrawn
- 1975-08-27 GB GB35420/75A patent/GB1479399A/en not_active Expired
- 1975-08-28 JP JP50103551A patent/JPS5177240A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1479399A (en) | 1977-07-13 |
| DE2537770A1 (en) | 1976-03-11 |
| JPS5177240A (en) | 1976-07-05 |
| US3929478A (en) | 1975-12-30 |
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