DE1497177B2 - - Google Patents

Info

Publication number
DE1497177B2
DE1497177B2 DE19651497177 DE1497177A DE1497177B2 DE 1497177 B2 DE1497177 B2 DE 1497177B2 DE 19651497177 DE19651497177 DE 19651497177 DE 1497177 A DE1497177 A DE 1497177A DE 1497177 B2 DE1497177 B2 DE 1497177B2
Authority
DE
Germany
Prior art keywords
photoconductive
weight
percent
alkaryl
alkyl
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
Application number
DE19651497177
Other languages
German (de)
Other versions
DE1497177A1 (en
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.)
Filing date
Publication date
Application filed filed Critical
Publication of DE1497177A1 publication Critical patent/DE1497177A1/en
Publication of DE1497177B2 publication Critical patent/DE1497177B2/de
Pending legal-status Critical Current

Links

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
    • G03G5/062—Acyclic or carbocyclic compounds containing non-metal elements other than hydrogen, halogen, oxygen or 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
    • G03G5/0601—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
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine
    • 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
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine
    • G03G5/06144—Amines arylamine diamine

Description

Die Erfindung betrifft eine übersensibilisierte photoleitfahige Zinkoxyd - Bindemittel - Schicht mit einem Sensibilisierungsfarbstoff.The invention relates to an oversensitized photoconductive zinc oxide binder layer with a sensitizing dye.

Es ist bekannt (USA.-Patentschriften 3 010 883, 3 010 884), elektrophotographische Aufzeichnungsmaterialien für die elektrolytische Entwicklung zu sensibilisieren. Weil das Kopierblatt zweckmäßig eine weiße Farbe erhalten soll, wird die Konzentration des Sensibilisierungsfarbstoffs möglichst gering gehalten. It is known (U.S. Patents 3,010,883, 3,010,884), electrophotographic recording materials to raise awareness of electrolytic development. Because the copy sheet is convenient If a white color is to be obtained, the concentration of the sensitizing dye is kept as low as possible.

Es ist ferner bekannt, photoleitfahige Schichten gleichzeitig mit zwei Farbstoffen zu sensibilisieren, wobei übersensibilisierung auftritt (Sei. Ind. Phot., 34 [1963], Nr. 3, S. iOO).It is also known to sensitize photoconductive layers simultaneously with two dyes, where oversensitization occurs (Sei. Ind. Phot., 34 [1963], No. 3, p. 100).

Aufgabe der Erfindung ist, die Empfindlichkeit einer photoleitfähigen Zinkoxyd-Bindemittel-Schicht zu erhöhen, ohne daß dadurch die Schicht eine stärkere Färbung und erhöhte Dunkelleitfähigkeit aufweist. The object of the invention is to improve the sensitivity of a photoconductive zinc oxide binder layer to increase without the layer having a stronger color and increased dark conductivity.

Der Gegenstand der Erfindung geht von einer übersensibilisiertenphotoleitfähigenZnO-Bindemittel-Schicht mit einem Sensibilisierungsfarbstoff aus und ist dadurch gekennzeichnet, daß die Schicht als Ubersensibilisator einen Komplexbildner für Zn-Ionen mit der Gruppe Vorzugsweise enthält die photoleitfahige Schicht als Ubersensibilisator eine Verbindung der FormelThe invention relates to an oversensitized photoconductive ZnO binder layer with a sensitizing dye and is characterized in that the layer as Supersensitizer a complexing agent for Zn ions with the group The photoconductive layer preferably contains a compound of the formula as a supersensitizer

Y —Y -

enthält, worin R1 und R2 gleich H, Alkyl, Alkaryl oder gleich den zur Vervollständigung eines 5- oder 6-Ringes erforderlichen Atomen sind, Y gleichcontains, where R 1 and R 2 are H, alkyl, alkaryl or the atoms required to complete a 5- or 6-ring, Y is the same

-CH3 = N-(-N = CH-).--CH 3 = N - (- N = CH -) .-

SO3HSO 3 H

oderor

4040

4545

oder — CHR3 -NH-R3 gleich H, Alkyl, Alkaryl oder Aryl und η gleich 0 oder 1 ist.or - CHR 3 -NH-R 3 is H, alkyl, alkaryl or aryl and η is 0 or 1.

Verbindungen, wie Ν,Ν-Dimethylanilin, haben praktisch keine übersensibilisierende Wirkung, dagegen p-Dimethylaminobenzaldehyd und p-Dimethylaminobenzoesäure. Die bevorzugten Ubersensibilisatoren sind keine Sensibilisierungsfarbstoffe, d. h., sie sensibilisieren allein angewendet photoleitfähiges Zinkoxyd nicht.Compounds such as Ν, Ν-dimethylaniline have practically no oversensitizing effect, on the other hand p-dimethylaminobenzaldehyde and p-dimethylaminobenzoic acid. The preferred hypersensitizers are not sensitizing dyes; H., they do not sensitize photoconductive zinc oxide when used alone.

Durch die Erfindung wird erreicht, daß neben einer wesentlichen Erhöhung der Empfindlichkeit der photoleitfähigen ZnO-Bindemittel-Schicht letztere nicht durch größere Mengen Sensibilisierungsfarbstoffen gefärbt erscheint. Die übersensibilisierte photoleitfahige Schicht hat ferner praktisch keine heraufgesetzte Dunkelleitfähigkeit. Die erfindungsgemäßen Ubersensibilisatoren werden in Mengen von 0,0001 bis 1,5 Gewichtsprozent, vorzugsweise von 0,001 bis 1,5Gewichtsprozent, des Photoleiters' angewendet,The invention achieves that in addition to a substantial increase in the sensitivity of the photoconductive ZnO binder layer, the latter is not affected by larger amounts of sensitizing dyes appears colored. The oversensitized photoconductive layer also has practically none increased dark conductivity. The hypersensitizers according to the invention are used in amounts of 0.0001 to 1.5 percent by weight, preferably from 0.001 to 1.5 percent by weight, of the photoconductor ' applied,

Beispiele für Ubersensibilisatoren, die sämtlich die Empfindlichkeit mindestens auf das Doppelte erhöhen, sind in der Tabelle angegeben.Examples of hypersensitizers, all of which increase sensitivity at least twice as much, are given in the table.

C=N-C-NHC = N-C-NH

worin Ri und R-2 die oben angegebene Bedeutung haben.wherein Ri and R-2 have the meaning given above to have.

Die qualitative Ermittlung der relativen Wirksamkeit einer Verbindung als Ubersensibilisator kann leicht nach dem folgenden Verfahren erfolgen: Eine Dispersion wird hergestellt, indem ein Gemisch von 2867 g Zinkoxydpulver (U. S. P. 12), 2821 g Toluol, 100 ecm Methanol und 2026 g einer 30gewichtsprozentigen Lösung eines Styrol-Butadien-Mischpolymerisats (Gewichtsverhältnis 70 : 30) in Toluol mehrere Stunden auf der Kugelmühle vermählen wird. Die zu untersuchende Verbindung wird in einem Lösungsmittel, z. B. Methanol, zu einer Lösung von 2 Gewichtsprozent gelöst, und von dieser Lösung werden 3,1 ecm zu 200 g der Dispersion gegeben. Nach gründlichem Vermischen wird die Probe unter Raumbedingungen 24 Stunden stehengelassen. 3,5 ecm des folgenden Gemisches von Sensibilisierungsfarbstoffen werden dann vor dem überziehen zugesetzt:The qualitative determination of the relative effectiveness of a compound as a hypersensitizer can can easily be done according to the following procedure: A dispersion is prepared by adding a mixture of 2867 g of zinc oxide powder (U.S.P. 12), 2821 g of toluene, 100 ecm of methanol and 2026 g of a 30 weight percent Solution of a styrene-butadiene copolymer (weight ratio 70:30) in toluene is milled for several hours on the ball mill. The compound to be examined is in a solvent, e.g. B. methanol, dissolved to a solution of 2 percent by weight, and from this solution 3.1 ecm are added to 200 g of the dispersion. After thorough mixing, the sample is taken under Room conditions left to stand for 24 hours. 3.5 ecm of the following mixture of sensitizing dyes are then added before coating:

54 ecm einer Lösung von 0,2 Gewichtsprozent Sulfoflavin (CI. 56 205) in Methanol,54 ecm of a solution of 0.2 percent by weight sulfoflavin (CI. 56 205) in methanol,

27 ecm einer Lösung von 0,2 Gewichtsprozent Phloxin B (CI. 42410) in Methanol,27 ecm of a solution of 0.2 percent by weight phloxin B (CI. 42410) in methanol,

19 ecm einer Lösung von 0,5 Gewichtsprozent Alphazurine (C. I. 42 045) in Methanol.19 ecm of a solution of 0.5 percent by weight Alphazurine (C.I. 42 045) in methanol.

Andere Sensibilisierungsfarbstoffe (z. B. Cyanine, Xanthene, Merocyanine, Di- und Triphenylmethane) können ebenfalls verwendet werden, weil die Ubersensibilisatoren nicht spezifisch für bestimmte Sensibilisierungsfarbstoffe sind. Diese Dispersion wird mit dem Rakel auf einen leitenden Schichtträger, ζ. B. ein mit einer Aluminiumfolie beschichtetes Papierblatt 0,0178 mm dick (trocken gemessen), aufgebracht. Das Aufzeichnungsmaterial wird dann mit Licht einer Wellenlänge von 4450, 5500 und 6500 Ä durch einen Keil belichtet und in bekannter Weise elektrolytisch entwickelt. Eine Vergleichsprobe wird ohne die zu untersuchende Verbindung nach dem gleichen Verfahren hergestellt, belichtet und elektrolytisch entwickelt. Durch visuellen Vergleich der entwickelten Proben wird ermittelt, ob die zu untersuchende Verbindung eine übersensibilisierende Wirkung auf die photoleitfahige Schicht hat.Other sensitizing dyes (e.g. cyanines, xanthenes, merocyanines, di- and triphenylmethanes) can also be used because the hypersensitizers are not specific to certain sensitizing dyes are. This dispersion is applied to a conductive substrate with a doctor blade, ζ. B. one coated with an aluminum foil Paper sheet 0.0178 mm thick (measured dry), applied. The recording material is then with Light with a wavelength of 4450, 5500 and 6500 Å through a wedge and exposed in a known manner electrolytically developed. A comparison sample is without the compound to be examined after manufactured, exposed and electrolytically developed using the same process. By visual comparison of the developed samples is used to determine whether the compound to be investigated has an oversensitizing effect on the photoconductive layer.

(CH3)2N (CH3)2N CO, H(CH 3 ) 2 N (CH 3 ) 2 N CO, H

N(CH3),N (CH 3 ),

CH3NH-/ V-CO2HCH 3 NH- / V-CO 2 H

(CH3),N /-N(CH3),(CH 3 ), N / -N (CH 3 ),

(CH3)2N (CH3J2N(CH 3 ) 2 N (CH 3 J 2 N

CH = N-NHC CH = N-NHC

CO2HCO 2 H

(CH3)2N(CH 3 ) 2 N

I = N-NHC OH I = N-NHC OH

(CH3J2N -<"' \; C(CH 3 J 2 N - <"'\; C

(CHj)2N--(CHj) 2 N--

>~ N(CH3I2 > ~ N (CH 3 I 2

(CH3I2N -~i (CH 3 I 2 N - ~ i

(C2H5I2N(C 2 H 5 I 2 N

I!I!

C = NC — NH — CH, - CH = CH,C = NC - NH - CH, - CH = CH,

Il -C-Il -C-

>- N(CH,),> - N (CH,),

(C, H, I, N(C, H, I, N

C —C -

N(C2H5),N (C 2 H 5 ),

(CH1I2N(CH 1 I 2 N

(C2H5J2N(C 2 H 5 J 2 N

(C2H5I2N(C 2 H 5 I 2 N

C=NC- NHC = NC - NH

SO, HSO, H

SO3NaSO 3 Na

Claims (1)

Palentanspruch: .s Palent claim:. s Uberscnsibilisicrte photolcitlahigc ZnO-Bindcmittel-Schicht mit einem Sensibilisierungsfarbstoff, dadurch gekennzeichnet, daß sie als übersensibilisator' einen Komplexbildner für Zn-Ionen mit der GruppeSuper-sensitized, photoconductive ZnO binder layer with a sensitizing dye, characterized in that they as a supersensitizer 'a complexing agent for Zn ions with the group R,R, enthält, worin R, und R2 gleich H. Alkyl. Alkarylcontains, wherein R 1 and R 2 are H. alkyl. Alkaryl oder gleich den /ur Vervollständigung eines 5- oder 6-Ringes erforderlichen Atomen sind. Y gleichor equal to the atoms required to complete a 5- or 6-membered ring. Y same C C SO., -C C SO., - CR3 = N 1 N CH --)„-CR 3 = N 1 N CH -) "- oder — CHR;,— NH—. R:t gleich H. Alkyl. Alkaryl oder Aryl und ;/ gleich 0 oder 1 ist.or - CHR;, - NH—. R: t is H. alkyl. Alkaryl or aryl and; / is 0 or 1.
DE19651497177 1964-02-14 1965-02-12 Supersensitized photosensitive display material Pending DE1497177A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US344811A US3352670A (en) 1964-02-14 1964-02-14 Supersensitizers for optically sensitized photoconductive layers

Publications (2)

Publication Number Publication Date
DE1497177A1 DE1497177A1 (en) 1969-03-27
DE1497177B2 true DE1497177B2 (en) 1970-01-08

Family

ID=23352145

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19651497177 Pending DE1497177A1 (en) 1964-02-14 1965-02-12 Supersensitized photosensitive display material

Country Status (3)

Country Link
US (1) US3352670A (en)
DE (1) DE1497177A1 (en)
GB (1) GB1087273A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1497118A1 (en) * 1965-05-29 1969-04-17 Agfa Gevaert Ag Sensitized electrophotographic layers
DE1497120A1 (en) * 1965-10-15 1969-05-14 Agfa Gevaert Ag Sensitized electrophotographic layers
US3469979A (en) * 1965-11-26 1969-09-30 Dennison Mfg Co Electrophotographic recording element with increased speed
US4043813A (en) * 1973-06-06 1977-08-23 Bell & Howell Company Photoconductive particles of zinc oxide
EP0058839B1 (en) * 1981-02-23 1986-04-16 Minnesota Mining And Manufacturing Company Sensitized organic electron donor compounds

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE617032A (en) * 1961-04-29
US3271143A (en) * 1964-01-06 1966-09-06 Minnesota Mining & Mfg Photoconductor sheet material
US3271144A (en) * 1964-09-08 1966-09-06 Minnesota Mining & Mfg Supersensitized zinc oxide
US3197307A (en) * 1964-09-22 1965-07-27 Eastman Kodak Co Surface modification of zinc oxide and electrophotographic member therefrom

Also Published As

Publication number Publication date
DE1497177A1 (en) 1969-03-27
US3352670A (en) 1967-11-14
GB1087273A (en) 1967-10-18

Similar Documents

Publication Publication Date Title
DE2618757C3 (en) Electrically conductive substrate
DE3738638C2 (en) Photoconductive composition
DE3208455A1 (en) ELECTROPHOTOGRAPHIC LIGHT SENSITIVE PRINT MATERIALS
EP0274017A2 (en) Antistatic photographic support material
DE3018871A1 (en) LAYERED ELECTROPHOTOGRAPHIC PHOTO LADDER
DE1497177B2 (en)
DE2810466A1 (en) PHOTO-SENSITIVE MEDIUM FOR ELECTROPHOTOGRAPHY
DE1767931B2 (en) DIAGNOSTIC MEANS AND METHOD OF DETECTION OF UROBILINOGENOGEN BODER
DE1522556A1 (en) Electrographic printing process
DE2822761A1 (en) ELECTROPHOTOGRAPHIC RECORDING MATERIAL
DE2038274A1 (en) Spectrally Sensitized Electrophotographic Materials
DE1116057B (en) Material for electrophotographic reproduction
DE1220732B (en) Photographic recording material for the production of one or more colored, positive or negative images or of planographic printing plates
DE2902705A1 (en) METHOD OF SENSITIZING ZINC OXIDE WITH A SENSITIVITY DYE AND LIGHT SENSITIVITY LAYERS MANUFACTURED USING THE SENSITIVE ZINC OXIDE
DE2747143A1 (en) ELECTROPHOTOGRAPHIC LIGHT SENSITIVE PARTS
DE2211183C3 (en) New sensitizing dyes, process for their preparation and their use
DE2113995C3 (en) Basically substituted fluoran compounds and their use as color formers for pressure-sensitive copier papers
DE2822763A1 (en) ELECTROPHOTOGRAPHIC RECORDING MATERIAL
DE3036946C2 (en)
DE2038207C3 (en) Process for bleaching sensitizing dyes in a photoconductive layer
DE1817417C3 (en) Two component diazotype material
DE1772318C3 (en) Electrophotographic recording material
DE1597808A1 (en) Aqueous coating composition for photoelectrically conductive recording material
DE1930006C3 (en) Two-component light-sensitive diazotype material
DE2100158B2 (en) Electrophotographic recording material with a photoconductor-binder layer