DE1497108B2 - Photoconductive layer - Google Patents
Photoconductive layerInfo
- Publication number
- DE1497108B2 DE1497108B2 DE19641497108 DE1497108A DE1497108B2 DE 1497108 B2 DE1497108 B2 DE 1497108B2 DE 19641497108 DE19641497108 DE 19641497108 DE 1497108 A DE1497108 A DE 1497108A DE 1497108 B2 DE1497108 B2 DE 1497108B2
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- alkyl
- photoconductive layer
- radical
- 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.)
- Pending
Links
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 230000001235 sensitizing effect Effects 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052736 halogen Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- -1 N, N-disubstituted Amino group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 3
- 229940043267 rhodamine b Drugs 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- CEJANLKHJMMNQB-UHFFFAOYSA-M cryptocyanin Chemical compound [I-].C12=CC=CC=C2N(CC)C=CC1=CC=CC1=CC=[N+](CC)C2=CC=CC=C12 CEJANLKHJMMNQB-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical compound [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000758 substrate Substances 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
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/88—Hydrazones having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/36—One oxygen atom
- C07D263/42—One oxygen atom attached in position 5
-
- 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
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
-
- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
- G03G5/0631—Heterocyclic compounds containing one hetero ring being five-membered containing two hetero atoms
-
- 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
- G03G5/0664—Dyes
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
- G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Printing Plates And Materials Therefor (AREA)
Description
Die Erfindung betrifft eine photoleitfähige Schicht mit einem Ν,Ν-disubstituierte Aminogruppen enthaltenden Photoleiter, gegebenenfalls einem Bindemittel und gegebenenfalls einem Sensibilisierungsfarbstoff. The invention relates to a photoconductive layer having a Ν, Ν-disubstituted amino groups Photoconductor, optionally a binder and optionally a sensitizing dye.
Es ist bekannt, als Photoleiter Schiffsche Basen oder Acylhydrazone zu verwenden, die Ν,Ν-disubstituierte Aminogruppen enthalten (USA.-Patentschriften 3 041 165 und 3 066023).It is known to use Schiff's bases or acylhydrazones which are Ν, Ν-disubstituted as photoconductors Contain amino groups (U.S. Patents 3,041,165 and 3,066,023).
Nachteilig daran ist, daß diese Photoleiter nicht empfindlich genug sind.The disadvantage of this is that these photoconductors are not sensitive enough.
Aufgabe der Erfindung ist, photoleitfähige Schichten anzugeben, die eine erhöhte Empfindlichkeit haben.The object of the invention is to provide photoconductive layers which have an increased sensitivity.
Der Gegenstand der Erfindung geht von einer photoleitfähigen Schicht mit einem Ν,Ν-disubstituierte Aminogruppen enthaltenden Photoleiter, gegebenenfalls einem Bindemittel und gegebenenfalls einem Sensibilisierungsfarbstoff aus und ist dadurch gekennzeichnet, daß sie als Photoleiter ein Aminoarylidenazin der FormelThe object of the invention is based on a photoconductive layer with a Ν, Ν-disubstituted Photoconductor containing amino groups, optionally a binder and optionally a sensitizing dye and is characterized in that it is an aminoarylidenazine as a photoconductor the formula
durch Alkyl- oder Halogen substituierten — Arylenrest ist, R1 und R2 gleich oder verschieden sind und eine — gegebenenfalls durch OH oder Halogen substituierte — Alkyl-; Aralkyl- oder Alkenylgruppe bedeuten, zusammen gleich den zur Vervollständigung eines heterocyclischen 6-Ringes nötigen Atomen sind oder worin die Gruppeis arylene radical substituted by alkyl or halogen, R 1 and R 2 are identical or different and an alkyl-; Aralkyl or alkenyl groups, together are the same as the atoms necessary to complete a heterocyclic 6-membered ring, or in which the group
,R1 , R 1
— Ar—N- Ar-N
,5 gleich der Gruppe, 5 equal to the group
N-Ar-CH=N-N=CH-Ar-NN-Ar-CH = N-N = CH-Ar-N
ist.is.
R2/ XR2 R 2 / X R 2
Beispiele von N,N-disubstituierten Aminourylidenenthält, worin Ar gleich einem — gegebenenfalls azinen sind folgende:Contains examples of N, N-disubstituted aminourylidene, where Ar equals one - optionally azines are the following:
CH5 CH 5
C1HC 1 H
F. 188,5 bis 189,01C.F. 188.5 to 189.0 1 C.
CH3 CH 3
F. 250 bis 253C. (Beil. 14, 36).F. 250 to 253C. (Appendix 14, 36).
H HH H
N —/ \— C = N-N = CN - / \ - C = NN = C
C2H5'C 2 H 5 '
CH3 CH 3
F. 180 bis 182° C.F. 180 to 182 ° C.
CH3 CH 3
O /
O
y N
y
CH.,CH.,
F. 145,0 bis 146,5 C.F. 145.0 to 146.5 C.
CH,CH,
F. 197,5 bis 198,5 C.F. 197.5 to 198.5 C.
ClCl
ClCl
'C2H5 'C 2 H 5
Ν — V-C = N-N = C- '< Ν - VC = NN = C- '<
C2H5 C 2 H 5
ClCl
-N-N
C2H5 C 2 H 5
F. 226,5 bis 227,0 C.F. 226.5 to 227.0 C.
H N HH N H
H HH H
C = N-N = CC = N-N = C
-N-N
C,HS C, H S
CH,CH,
F. 164,0 bis 164,5 C.F. 164.0 to 164.5 C.
F. > 25 C (wird dunkel). CH2 = CH-CFI2SF.> 25 C (becomes dark). CH 2 = CH-CFI 2 S
. CH2 = CH-CH2 F. 99,0 bis 100,0 C.. CH 2 = CH-CH 2 F. 99.0 to 100.0 C.
CH2 = CH — CH2 F. 114 bis 115°C. CH 2 = CH - CH 2 mp 114-115 ° C.
— CH- CH
CH2 = CH — CH2 F. 141,5 bis 143° C. _ΧΤ_Κ,_Λ^^ \ CH 2 = CH - CH 2 F. 141.5 to 143 ° C. _ΧΤ_Κ, _Λ ^^ \
CHCH
■2 O5 ■ 2 O 5
y CH2 — CH = CH2 N . (12) y CH 2 - CH = CH 2 N. (12)
CH2 — CH = CH2 CH 2 - CH = CH 2
CH, CH — CH7 CH, CH - CH 7
CH, — OCH, - O
CH2-CH = CH2 (14) CH 2 -CH = CH 2 (14)
Cl — CH2 — CH2
Ι·". 145.5 bis 147,5 C.Cl - CH 2 - CH 2
Ι · ". 145.5 to 147.5 C.
HO — CH2 — CH2
F. 181,0 bis 184,5 C.HO - CH 2 - CH 2
F. 181.0 to 184.5 C.
Cl-C2H4 Cl-C 2 H 4
Cl-C2H4
F. 162.5 bis 163.0 C.Cl-C 2 H 4
F. 162.5 to 163.0 C.
C=N -N = C-:C = N -N = C-:
C2H5 C 2 H 5
CH2CH2ClCH 2 CH 2 Cl
(15)(15)
(16)(16)
(17)(17)
C2H4 - ClC 2 H 4 - Cl
Von den oben aufgerührten 17 Beispielen sind die Verbindungen (5), (8), (12). (13) und (17) bevorzugt bezüglich Löslichkeit und Empfindlichkeit. Dabei ist der Arylenrest gleich einem p-Phenylen- oder 6-Naphthylenrest, und die beiden endständigen Substitucnten sind gleich geradkcttigc Alkenylradikale mit 1 bis 3 Kohlenstoffatomen oder gleich Alkylradikale mit 1 bis 2 Kohlenstoffatomen, die endständig mit einem Halogenatom oder einer Phenylgruppc substituiert sind.Of the 17 examples listed above, the compounds (5), (8), (12) are. (13) and (17) are preferred regarding solubility and sensitivity. The arylene radical is equal to a p-phenylene or 6-naphthylene radical, and the two terminal substitutes are equal to straight alkenyl radicals with 1 to 3 carbon atoms or equal to alkyl radicals with 1 to 2 carbon atoms, which are terminated with a Halogen atom or a phenyl group are substituted.
In jedem Beispiel ist der Photoleitcr symmetrisch und hat nur tertiäre Aminostickstoffatomc.In each example the photoconductor is symmetrical and has only tertiary amino nitrogen atoms.
Gemäß einer Ausgestaltung der Erfindung enthält die photoleitfähige Schicht als Photoleiter ein Aminoarylidenazin der oben angegebenen Formel, worin die disubstituierten Aminogruppen in paraStellung zu einem Phenylcnrest oder in 4-, 5-, 6- oder 7-Stcllung zu einem Naphthylenrest stehen und die Verbindung einen Schmelzpunkt zwischen 99 und 250" C und ein Molekulargewicht zwischen 294 und 578 hat.According to one embodiment of the invention, the photoconductive layer contains a photoconductor Aminoarylidenazine of the formula given above, in which the disubstituted amino groups are in the para position to a phenyl radical or in the 4-, 5-, 6- or 7-position to a naphthylene radical and the Compound has a melting point between 99 and 250 "C and a molecular weight between 294 and 578 has.
Die angegebene Stellung der Aminogruppen ist bevorzugt, da ein solcher Rest besser mit dem konjugierte Doppelbindungen enthaltenden Verbindungsglied in Resonanz tritt. Gleiche Alkyl- oder Alkenylgruppen sind bevorzugt, da diese Gruppen dem Photolciter eine optimale Löslichkeit verleihen. Zusätzlich stehen solche Verbindungen im Handel zur so Verfügung.The stated position of the amino groups is preferred, since such a radical is better conjugated with the Link containing double bonds resonates. Same alkyl or alkenyl groups are preferred because these groups give the photociter an optimal solubility. Additionally such connections are commercially available.
Gemäß einer weiteren Ausgestaltung der Erfindung enthält die photoleitfähigc Schicht als Photoleiter ein soeben angegebenes, bevorzugtes Aminoarylidenazin, in dem der Phenylenrcst in o-Stellung durch CH3 oder Cl substituiert ist.According to a further embodiment of the invention, the photoconductive layer contains, as a photoconductor, a preferred aminoarylidenazine in which the phenylene residue is substituted in the o-position by CH 3 or Cl.
Durch die Erfindung wird erreicht, daß die photoleitfahigen Schichten fünfmal empfindlicher sind als die Schiffschen Basen oder Acylhydrazone. Außerdem bilden die Photoleiter schnell feste Lösungen in dem Bindemittel der photolcitfähigen Schicht, aus denen sie nicht zum Kristallisieren neigen. Weiterhin sind die Photoleiter einfach herzustellen, stabil und daher von langer Lagerfähigkcit.The invention achieves that the photoconductive Layers are five times more sensitive than Schiff's bases or acylhydrazones. aside from that the photoconductors quickly form solid solutions in the binder of the photoconductive layer from which they do not tend to crystallize. Furthermore, the photoconductors are easy to manufacture, stable and therefore of long shelf life.
Als Bindemittel, Lösungsmittel und Schichtträger zur Herstellung elcktrophotographischer Aufzeichnungsmatcrialien sind alle bekannten geeignet. Die festen photolcitfähigen Schichten sind transparent.As a binder, solvent and support for the production of electro-photographic recording materials all known ones are suitable. The solid photoconductive layers are transparent.
Die Ν,Ν-disubstituiertcn Aminoarylidenazine werden vorzugsweise in einem Gewichtsanteil von 25% der photolcitfähigen Schicht verwendet.The Ν, Ν-disubstituted aminoarylidenazines are preferably used in a proportion by weight of 25% of the photoconductive layer.
Die Photoleiter werden durch Kondensation von N.N-disubstituicrten Aminoarylaldchyden mit Hydrazin hergestellt. Ein Beispiel ist die Herstellung von bis-4.4'-uimethylaminobenzylidenazin,· wie man es in Bcilstein. 14, 36. findet.The photoconductors are made by condensation of N.N-disubstituted aminoaryl aldehydes with hydrazine manufactured. An example is the production of bis-4,4'-uimethylaminobenzylidenazine, as described in Bcilstein. 14, 36. takes place.
Die auf 100 bis 400 V aufgeladenen photoleitfähigcn Schichten sind für Licht einer Wellenlänge zwischen 350 und 420 nm empfindlich.The photoconductive charged to 100 to 400 V. Layers are sensitive to light with a wavelength between 350 and 420 nm.
Die Spektralcmpfindlichkeit der photoleitfähigcn Schichten kann durch bekannte Scnsibilisierungsfarbstoffe. vorzugsweise wasserlösliche quartärc Ammonium- und Oxoniumfarbsioffe. in den sichtbaren Bereich verschoben und die allgemeine Empfindlichkeit erhöht werden.The spectral sensitivity of the photoconductive layers can be determined by known sensitizing dyes. preferably water-soluble quaternary ammonium and oxonium dyes. in the visible area shifted and the general sensitivity increased.
Eine Lösung aus 1 g bis-4.4'-Diallylaminobenzylidcnazin [Formel (12)]. 2,5 g Polyvinylbutyral, 50 mg Kristallviolett und 50 ml Mcthyläthylketon wird auf vorgestrichenes Papier in einer Menge zwischen 5 und 10 g (trocken gemessen) pro 1,4925 m2 aufgebracht. Das beschichtete Papier wird an der Luft oder einige Minuten lang in einem Ofen bei 60 bis KK) C getrocknet. Das so hergestellte elektrophotographische Aufzeichnungsmaterial wird positiv unter einer Koronaentladung geladen und dann unter einer positiven transparenten Kopiervorlage mit einer 60-Watt-Wolframlampe belichtet. Die Entwicklung mit einem Pulverentwickler erfolgt unter einer roten Lampe. Der Toner haftet an den nicht belichteten Bildtcilen und ergibt ein positives Tonerbild. Das Tonerbild wird dann kurze Zeit auf 100 bis 130'C erhitzt, um es zu fixieren.A solution of 1 g of bis-4,4'-diallylaminobenzylidincnazine [formula (12)]. 2.5 g of polyvinyl butyral, 50 mg of crystal violet and 50 ml of methyl ethyl ketone are applied to prepainted paper in an amount between 5 and 10 g (measured dry) per 1.4925 m 2 . The coated paper is dried in the air or in an oven at 60 to KK) C for a few minutes. The electrophotographic recording material produced in this way is positively charged under a corona discharge and then exposed to a 60 watt tungsten lamp under a positive, transparent master copy. Development with a powder developer takes place under a red lamp. The toner adheres to the unexposed parts of the image and results in a positive toner image. The toner image is then heated to 100 to 130 ° C for a short time in order to fix it.
Zur Herstellung von Flachdruckformen wird ein Schichtträger mit einer Lösung aus 1.0 g bis-4,4-Diäthylaminobenzylidenazin [Formel (I)], 2,5 g Polyvinylbutyral, 50 mg Rhodamin B und 50 ml Chloroform beschichtet, in der oben beschriebenen Weise weiterverarbeitet und bei 140 bis 160C fixiert. Dann wird die photoleitfähige Schicht mit Methanol ausgewaschen, wodurch an den nicht mit hydrophobem.For the production of planographic printing forms, a substrate with a solution of 1.0 g of bis-4,4-diethylaminobenzylidenazine is used [Formula (I)], 2.5 g of polyvinyl butyral, 50 mg of rhodamine B and 50 ml of chloroform coated, further processed in the manner described above and fixed at 140 to 160C. then the photoconductive layer is washed out with methanol, which means that those not with hydrophobic.
unlöslichem Toner bedeckten Bildteilen der hydrophile Schichtträger erscheint.insoluble toner covered parts of the image of the hydrophilic support appears.
An Stelle von Methanol können Mischungen von sirupartiger Phosphorsäure mit Alkoholen mit oder ohne kleiner Mengen Salzsäure oder Schwefelsäure als ausgezeichnete Waschlösungen verwendet werden, da die Photoleiter säurelöslich sind.Instead of methanol, mixtures of syrupy phosphoric acid with alcohols with or without small amounts of hydrochloric acid or sulfuric acid are used as excellent washing solutions, since the photoconductors are acid-soluble.
Beispiel III Example III
Eine Lösung aus 1,0 g bis-4,4'-Diäthylamino-2,2-di- ό methylbenzylidenazin (Formel 3), 2,5 g Polyvinylbutyral, 50 mg Kryptocyanin und 50 ml Chloroform wird wie im Beispiel I verarbeitet.A solution of 1.0 g of bis-4,4'-diethylamino-2,2-di- ό methylbenzylidenazine (Formula 3), 2.5 g polyvinyl butyral, 50 mg cryptocyanine and 50 ml chloroform is processed as in example I.
B e i s ρ i e 1 IVB e i s ρ i e 1 IV
Eine Lösung aus 1,0 g bis-4,4'-Dibenzylaminobenzylidenazin [Formel (5)], 2,5 g eines Mischpoly-' merisats aus 87 Gewichtsprozent Vinylchlorid und 13 Gewichtsprozent Vinylazetat und 50 mg Rhodamin B wird in einer Mischung aus 25 ml Chloroform und 25 ml Methyläthylketon gelöst und wie im Beispiel I oder II weiterverarbeitet.A solution of 1.0 g of bis-4,4'-dibenzylaminobenzylidenazine [formula (5)], 2.5 g of a mixed polymer of 87 percent by weight vinyl chloride and 13 percent by weight vinyl acetate and 50 mg of rhodamine B is in a mixture of 25 ml of chloroform and 25 ml of methyl ethyl ketone dissolved and processed as in Example I or II .
Eine Lösung aus 0,5 g bis - 4,4' - Diäthylamino-2,2',6,6'-tetrachlorbenzylidenazin [Formel (9)], 0,5 g bis-4,4'-Morpholinbenzylidenazin [Formel (6)], 2,5 g Polyvinylbutyral 50 mg Rhodamin B und 50 ml Chloroform wird wie im Beispiel I oder II weiterverarbeitet.A solution of 0.5 g of bis-4,4'-diethylamino-2,2 ', 6,6'-tetrachlorobenzylidenazine [Formula (9)], 0.5 g of bis-4,4'-morpholine benzylidenazine [Formula (6)], 2.5 g of polyvinyl butyral, 50 mg of rhodamine B and 50 ml of chloroform is processed further as in example I or II.
Eine Lösung aus 1,0 g bis-4,4'-DiallylaminobenzyIidenazin [Formel (12)], 2,0 g Polyvinylidenchlorid und 25 mg Pinacyanol wird in 50 ml Methyläthylketon gelöst und wie im Beispiel I oder II weiterverarbeitet.A solution of 1.0 g of bis-4,4'-DiallylaminobenzyIidenazin [formula (12)], 2.0 g of polyvinylidene chloride and 25 mg of pinacyanol is dissolved in 50 ml of methyl ethyl ketone and processed further as in Example I or II.
Claims (3)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30064763A | 1963-08-07 | 1963-08-07 | |
| US300617A US3290147A (en) | 1963-08-07 | 1963-08-07 | Electrophotographic organic photoconductors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1497108A1 DE1497108A1 (en) | 1969-10-30 |
| DE1497108B2 true DE1497108B2 (en) | 1970-03-26 |
Family
ID=26971869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641497108 Pending DE1497108B2 (en) | 1963-08-07 | 1964-07-23 | Photoconductive layer |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3290147A (en) |
| BE (2) | BE651472A (en) |
| DE (1) | DE1497108B2 (en) |
| DK (1) | DK112837B (en) |
| GB (1) | GB1016969A (en) |
| NL (2) | NL6409093A (en) |
| SE (1) | SE305588B (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3542546A (en) * | 1966-11-29 | 1970-11-24 | Eastman Kodak Co | Organic photoconductors containing the >n-n< nucleus |
| US3624226A (en) * | 1970-03-09 | 1971-11-30 | Calgon Corp | Electrographic organic photoconductor comprising of n,n,n{40 ,n{40 , tetrabenzyl 4,4{40 oxydianaline |
| US3692834A (en) * | 1971-02-25 | 1972-09-19 | Smith Kline French Lab | Intermediates for preparing acridines |
| US3765884A (en) * | 1971-07-06 | 1973-10-16 | Eastman Kodak Co | 1-substituted-2-indoline hydrazone photoconductors |
| US3767393A (en) * | 1971-11-11 | 1973-10-23 | Kodak Park Division | Alkylaminoaromatic organic photoconductors |
| US4252564A (en) * | 1979-08-21 | 1981-02-24 | The United States Of America As Represented By The United States Department Of Energy | Method for cleaning bomb-reduced uranium derbies |
| US4293714A (en) * | 1980-03-20 | 1981-10-06 | Gaf Corporation | Copolymerizable, ultraviolet light absorber 4-alkoxy-2'-allyloxybenzazines |
| US4420548A (en) * | 1980-11-28 | 1983-12-13 | Canon Kabushiki Kaisha | Electrophotographic member with hydrazone or ketazine compounds |
| JPS57148749A (en) * | 1981-03-11 | 1982-09-14 | Fuji Photo Film Co Ltd | Electrophotographic receptor |
| NL8200331A (en) * | 1982-01-29 | 1983-08-16 | Oce Nederland Bv | MULTILAYER ELECTROPHOTOGRAPHIC ELEMENT. |
| CN106380423B (en) * | 2016-08-25 | 2018-03-30 | 中国科学院上海微系统与信息技术研究所 | The compound of the detectable organophosphate nerve agents analogies of one kind and its application |
| CN109704988B (en) * | 2019-01-04 | 2020-06-16 | 北京师范大学 | Dihydrazone compound with high affinity with A β protein and Tau protein, derivative and application thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL218635A (en) * | 1956-07-04 | |||
| BE585419A (en) * | 1958-12-19 |
-
1963
- 1963-08-07 US US300617A patent/US3290147A/en not_active Expired - Lifetime
-
1964
- 1964-07-07 GB GB27993/64A patent/GB1016969A/en not_active Expired
- 1964-07-23 DE DE19641497108 patent/DE1497108B2/en active Pending
- 1964-07-31 SE SE9290/64A patent/SE305588B/xx unknown
- 1964-08-06 BE BE651472D patent/BE651472A/xx unknown
- 1964-08-06 DK DK389864AA patent/DK112837B/en unknown
- 1964-08-06 BE BE651473A patent/BE651473A/xx unknown
- 1964-08-07 NL NL6409093A patent/NL6409093A/xx unknown
- 1964-08-07 NL NL6409096A patent/NL6409096A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE305588B (en) | 1968-10-28 |
| DE1497108A1 (en) | 1969-10-30 |
| NL6409096A (en) | 1965-02-08 |
| NL6409093A (en) | 1965-02-08 |
| GB1016969A (en) | 1966-01-12 |
| BE651473A (en) | 1965-02-08 |
| DK112837B (en) | 1969-01-20 |
| US3290147A (en) | 1966-12-06 |
| BE651472A (en) | 1965-02-08 |
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