US3257203A - Electrophotographic reproduction material - Google Patents

Electrophotographic reproduction material Download PDF

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Publication number
US3257203A
US3257203A US834417A US83441759A US3257203A US 3257203 A US3257203 A US 3257203A US 834417 A US834417 A US 834417A US 83441759 A US83441759 A US 83441759A US 3257203 A US3257203 A US 3257203A
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grams
oxazole
chlorophenyl
formula
phenyl
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US834417A
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Sus Oskar
Neugebauer Wilhelm
Lind Erwin
Klupfel Kurt Walter
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Azoplate Corp
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Azoplate Corp
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    • 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
    • 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
    • C07D263/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
    • G03G5/0661—Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring

Definitions

  • This invention relates to an electrophotographic reproduction material.
  • the electrophotographic process also known as xerography
  • xerography is .becoming of increasing practical importance
  • An electrostatic charge is applied to the photo-conductive insulating layer;
  • the charged material is exposed to light beneath an original, so that the electrostatic charge is leaked away in'the parts of the layer struck by light.
  • the invisible electrostatic image thereby produced is made visible (developed) by applying a finely divided synthetic resin having an opposite electrostatic charge and given permanent (fixed) for example, by the application of heat to the support to fuse the resin into the base sheet.
  • the powder image may be transferred to another sheet before fusing.
  • Known materials used for the preparation of the photoconductive insulating layers required for the aforedescribed process include selenium, sulphur, zinc oxide, and also organic substances such as anthracene or anthraquinone. Consideration has also been given to a method of preparing the photoconductive insulating layers whereby the photoconductive substances in association with binders are dispersed in solvents, applied thus to electrically conductive supports, primarily metal foils and dried.
  • the electrophotographic material thus obtained has not yet satisfied the extensive demands made of modern duplicating material with'respect to range of use, reliability, simplicity in handling, and not least in importance, light sensitivity and keeping qualities.
  • an electrophotographic reproduction material comprising a base material coated with a thin uniform coherent photoconductive insulating layer adhereing thereto consisting of at least one substituted oxazole corresponding to the general formula:
  • R stands for a residue selected from the group consisting of hydrogen, aryl, alkenyl, alkyl, substituted aryl and heterocyclic radicals, I
  • R stands for a residue selected from the group consisting of hydrogen, alkyl, alkylated aminoaryl and aryl radicals,
  • R stands for a residue selected from the group consisting of hydrogen, aryl and substituted aryl radicals.
  • R stands for aminophenyL or dialkylaminophenyl radicals
  • R stands for phenyl or substituted phenyl radicals
  • R stands for hydrogen, alkyl, alkenyl or heterocyclic radicals
  • R and R stand for phenyl or substituted phenyl radicals
  • ,R stands for hydrogen or alkyl radicals.
  • a-acyl-amino ketones by a ring closure with concentrated sulfuric acid, or from aldehydes and aldehyde-cyano-hydrines which are reacted upon with gaseous hydrochloric acid in absolute ether.
  • 4,5-diphenyl-oxazoles according to the present invention are prepared by condensation of benzoines with hydrocyanic acid or with aliphatic nitriles, using sulfuric acid or poly-phosphoric acid as a condensing agent.
  • 2,4,5-triphenyl-oxazoles are prepared from benzoines and aromatic nitriles.
  • 2,4-diphenyloxazoles to be used according to the present invention are formed when w-bromo-acetophenone is fused with benzamides.
  • the phenyl groups of the oxazoles may be substituted, e.g. by halogen as fluorine, chlorine, bromine, iodine and by lower alkoxy groups as methoxy, ethoxy, butoxy.
  • 2-(4-aminophenyl)-5-phenyl-oxazo1e corresponding to Formula 1, melting point 188 C. is prepared from 12.1 grams of 4-aminobenzaldehyde and 13.3 grams of benzaldehydecyano-hydrine by a condensation by means of gaseous hydrochloric acid in absolute ether, while cooling with ice. After several hours the precipitated hydrochloride is filtered OE With suction, dissolved in a caustic soda solution, and the oxazole is extracted by ether. The ether solution'is agitated with a 30% solution of sodium hydrogen sulfite and dried. After evaporation of the ether, the residue is recrystallized from alcohol.
  • the above acetophenone is prepared by heating 11 grams of the hydrochloride of 4-dimethyl-amino-benzoylchloride and 8.6 grams of w-amino-acetophenone-hydrochloride in 75 cc. of pyridine.
  • 2-(4'-dirnethylamino-phenyl)-5 (4' chlorophenyl)- oXazole corresponding to Formula 4 is prepared from the hereinafter described oc-acylaminoketone by ring-closure with concentrated sulfuric acid. After recrystallization from methanol, the compound forms light yellow crystals which melt when heated to 134 C.
  • the ot-acylarninoketone used is obtained by reaction of 5 grams of 4-chloro-ot-amino-acetophenone hydrochloride with 5.4 grams of dimethylaminobenzoyl chloride.
  • 4-(4-dimethylaminophenyl)-5 (2' chlorophenyl)- oXazole corresponding to Formula 5 is obtained by condensing 20 grams of 2-chloro-4-dimethylaminobenzoin with 40 grams of potassium cyanide in 500 cc. of concentrated sulfuric acid. After recrystallization from a light petroleum fraction colorless crystals are obtained which melt at 122 C.
  • 2-vinyl-4-(4-dirnethylaminophenyl) 5 (2 chlorophenyl)-oxazole corresponding to Formula 6 is obtained by condensing 5.78 grams of 2'-chloro-4-dimethylaminobenzoin with 1.06 grams of acrylonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from a light petroleum fraction light yellow crystals are obtained which melt at 95 C.
  • 2-methyl-4-(4-dimethylaminophenyl)-5 (4' chlorophenyl)-oxazole corresponding to Formula 7 is obtained by condensing 5.78 grams of 4-chloro-4-dimethylaminobenzoin with 0.82 grams of acetonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from ethanol, colorless crystals are obtained which melt at 134 C.
  • 2-(4'-dimethylaminophenyl)-4,5-diphenyl-oxazole corresponding to Formula 8 is obtained by condensing 6.3 grams benzoin and 4.7 grams of 4-dimethyl-amino-benzonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from ethanol, light yellow crystals are obtained which melt when heated to 143 C. First the benzoin and the 4-dimethyl-amino-benzonitrile are intimately ground in a mortar, and then 60 grams of concentrated sulfuric acid are added as a condensing agent and the whole is left to stand for several hours at room temperature.
  • the reaction mixture is cautiously poured onto a mixture of ice and caustic soda solution, while stirring.
  • the precipitated oxazole is filtered off with suction, dried, dissolved in benzene and finally passed through a column filled With A1 By this last treatment the resinous products are held back which had been formed during the condensation in concentrated sulfuric acid.
  • the oxazole is removed from the Al O -column by washing with benzene. After evaporation of the benzene the oxazole is obtained in an almost pure state and may be recrystallized for further purification.
  • 2,5-diphenyl-4-(4-dimethylaminophenyl)-oxazo1e corresponding to Formula 9 is obtained by condensing 11 grams of 4-dimethy1-aminobenzoin with 4,7 grams of benzonitrile in 83 grams of concentrated sulfuric acid. After recrystallization from alcohol light yellow crystal are obtained which melt at 108 C.
  • 2-phenyl-4-(4-dimethylaminophenyl) (2'-chlorophenyD-oxazole corresponding to Formula is obtained in the form of light yellow crystals (melting point 140 C.) by condensing 9.9 grams of 2-chloro-4-dimethylamino benzoin with 3.5 grams of benzonitrile in 60 grams of concentrated sulfuric acid.
  • 2-phenyl-4-(4'-dimethylaminophenyl) 5 (4'-chlorophenyl)-oxazole corresponding to Formula 11 is obtained by condensing 9.9 grams of 4'-chloro-4-dimethylaminobenzoin with 3.5 grams of benzonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from ethanol yellow green crystals are obtained which melt at 132 C.
  • 2,5-diphenyl-4-(4'-dimethylaminophenyl)-oxazole corresponding to Formula 12 is obtained by condensing 7.1 grams of 4-diethyl-aminobenzoin with 2.6 grams of benzonitrile in 60 grams of concentrated sulfuric acid. For purification, the compound is dissolved in' hydrochloric acid and reprecipitated by adding sodium bicarbonate to the solution.
  • 2-(4'-dimethylaminophenyl) 4 (4 dimethylarninophenyl)-5-phenyl-oxazole corresponding to Formula 13 is obtained by condensing 5.66 grams of 4-diethylaminobenzoin and 2.92 grams of 4-dimethylaminobenzonitrile in 60 grams of concentrated sulfuric acid. For purification, the compound is dissolved in hydrochloric acid and reprecipitated by adding a sodium carbonate solution.
  • 2-(4f-dimethylaminophenyl) 4 (4 dimethylaminophenyl)-5-phenyl-oxazole corresponding to Formula 14 is obtained by condensing 5.1 grams of 4-dimethylaminobenzoin and 2.92 grams of 4-dimethylaminobenzonitrile in 60 grams of concentrated sulfuric acid. For purification, the compound is dissolved in hydrochloric acid and reprecipitated by adding a sodium carbonate solution.
  • 2,4-di-(4-diethylarninophenyl) 5 phenyl oxazole corresponding to Formula 15 is obtained by condensing 5.66 grams of 4-diethylaminobenzoin and 3.52 grams of 4-diethylaminobenzonitrile in' 60 grams of concentrated sulfuric acid at a temperature of 40-50 C. For purification, the compound is dissolved in hydrochloric acid and reprecipitated by adding a sodium carbonate solution.
  • 2-(2-chlorophenyl) 4 (4' diethylaminophenyl)-5- phenyl-oxazole corresponding to Formula 17 is prepared by condensing 5.66 grams of 4-diethylaminobenzoin and 2.74 grams of 2-chlorobenzonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from alcohol the compound forms light yellow crystals which melt at 83 C;
  • 2-(3'-chlorophenyl) 4 (4' diethylarninophenyl) 5- phenyl-oxazole corresponding to Formula 18 is obtained by condensing 5.66 grams of 4-diethylaminobenzoin and 2.74 grams of 3-chloro-benzonitrile-in 60 grams of concentrated sulfuric acid and recrystallization from alcohol. The compound melts at 99 C.
  • 2-(4'-chlorophenyl) 4 (4' diethylaminophenyl) 5- phenyl-oxazole corresponding to Formula 19 is obtained by condensing 5.66 grams of 4-diethylaminobenzoin and 2.74 grams of 4-chlorobenzonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from alcohol, colorless crystals are obtained which melt at C.
  • 2-(4'-chlorophenyl) 4 (4 dimethylaminophenyl)-5- phenyl-oxazole corresponding to Formula 20 is obtained by condensing 5.1 grams of 4-dimethylaminobenzoin and 2.74 grams of 4-chlorobenzonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from alcohol the light yellow compound melts at 147 C.
  • 2-(3'-cl1loro phenyl) 4 (4 dimethyl amin-ophenyD-5- phenyl-oxazole corresponding to Formula 21 is obtained by condensing 5 .1 grams of 4-dimethylaminobenzoin with 2.74 grams of 3-chlorobenzonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from alcohol, yellow crystals are formed which melt at 106 C.
  • 2-(4'-dimethylaminophenyl) 4 (4 dimethylaminophenyl)-5-(3-chlorophenyl)-oxazole corresponding to Formula 23 is obtained by condensing 5.78 grams of 4-dimethylamino-3'-chlorobenzoin and 2.92 grams of 4-dimethylaminobenzonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from alcohol, yellow crystals are formed which melt at 153 C.
  • 2,4 di (4' dimethylaminophenyl) 5 (2' chlorophenyl)-oxazole corresponding to Formula 24 is obtained by the reaction of 5.78 grams of 2'-chloro-4-dimethylaminobenzoin with 2.92 gramsof 4-dimethylaminobenzonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from alcohol, light yellow crystals are formed which melt at 164 C.
  • 2,4 di 4 dirriethylami-nophenyl) 5 (4 chlorophenyl)-oxazole corresponding to Formula 25 is obtained by condensing 5.78 grams of 4'-chloro-4-dimethylaminobenzoin and 2.92 grams of 4-dimethylaminobenzonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from alcohol, colorless crystals are obtained which melt at 143 C.
  • 2-(4-diethylaminophenyl) 4 (4' dimethylaminophenyl) 5 (4'-chlorophenyl)-oxazole corresponding to Formula 26 is obtained by condensing 5.78 grams of 4'- vchloro-4-dimethylaminobenzoin with 3.5 grams of 4-dicrystals are obtained which melt at 124 C.
  • 2-(2-chlorophenyl) 4 (4'.-dimethylaminophenyl)-5- (2'-chlorophenyl)-oxazole corresponding to Formula 27- ,is obtained by condensing 5.78 grams of 2'-chloro-4-dimethylaminobenzoi-n with 2.74 grams of 2-chlorobenzonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from alcohol, the compound melts at 154 C.
  • 2-(2'-chlorophenyl) 4 (4'-dimethylaminophenyl)-5- (4'-chlorophenyl)-oxazole corresponding to Formula 28 is obtained by condensing 5.78 grams of 4-chloro-4-dimethylaminobenzoin with 2.74 grams of 2-ch1orobenzonitrile in 60 grams of concentrated sulfuric acid. After recrystallization from alcohol, the compound forms yellow crystals which melt at 136 C.
  • propyl 4 (4' dimethylaminophenyl) 5 (4- chlorophenyD-oxazole corresponding to Formula 37 is obtained by condensing 1.38 grams of butyronitrile with 5.78 grams of 4'-chloro-4-dimethyl-aminobenzoin in 60 grams of concentrated sulfuric acid. After recrystallization from alcohol, the compound melts at 102 C.
  • the compounds corresponding to Formulae 41 and 42 may be prepared.
  • the compound .of Formula 41 i.e. the 2-vinyl-4-(4'-diprop ylaminophenyl)5-(2-ch1orophenyl)-oxazole, is obtained by condensing 1.06 grams of acrylonitrile with 6.9 grams of 2-chloro 4 dipropylaminobenzoin. After recrystallization from petroleum ether, the compoundforms lightyellow crystals which melt. at 77 C.
  • the compound of Formula 42 i.e.
  • the 2-vinyl-4-(4-dibutylaminophenyl)- 5-(2'-chlorophenyl)-oxazole is obtained by condensing 11 1.06 grams of acrylonitrile with 7.5 grams of 2'-chloro- 4-dibutylaminobenzoin. By rubbing with some petroleum ether, yellow crystals are obtained which melt at 50-51 C. The compound is very readily soluble in organic solvents and cannot be recrystallized.
  • the substituted oxazole compounds utilized according to the present invention are advantageously used as a solution in an organic solvent, e.g. benzene, acetone, methylene-chloride, ethyleneglycol monomethylether for coating the base material and evaporating the solvent to form a thin uniform coherent photoconductive layer adhering thereto.
  • an organic solvent e.g. benzene, acetone, methylene-chloride, ethyleneglycol monomethylether
  • the amino-phenyl substituted oxazole compounds utilized according to the present invention may be used in admixture with at least one other organic photoconductive substance.
  • the photoconductive insulating layers may include at least one water-insoluble organic resin in association with the oxazole compound.
  • Natural and synthetic resins e.g. balsam resins, phenol resins modified with colophony, and other resins of which colophony constitutes the major part, coumarone resins and indene resins, and the substances covered by the collective term synthetic lacquer resins, which according to the Kunststofftaschenbuch (Plastics Pocket Book) published by Saechtling-Zebrowski (11th edition, Kunststoff, 1955, page 212 forward) include:
  • polymers such as the polyvinyl chlorides, polyvinyl acetates, polyvinyl acetals, polyvinyl ethers, polyacrylic and polyrnethacrylic esters, as also polystyrene and isobutylene;
  • polycondensates e.g. polyesters, such as phthalate resins, alkyd resins, maleinate resins, maleic acidcolophony-mixed esters of higher alcohols, pheno1- formaldehyde resins, particularly colophony-modified phenol-formaldehyde condensates, urea-formaldehyde resins, melamine-formaldehyde condensates, aldehyde resins, ketone resins of which particular mention is to be made of AW 2 resins of the firm 12 Badische Anilinund Soda-Fabrik, xylene formaldehyde resins and polyamides; and
  • polyadducts such as polyurethanes.
  • the proportion of resin to photo-conductivesubstance may vary very greatly.
  • the use of mixtures of approximately equal parts of resin and oxazole compounds has been found to be advantageous. If the mixtures used consist of about equal parts of resin and oxazole compound, the solutions after coating and drying in most cases form clear layers which can be regarded as solid solutions.
  • the base materials used as supports for the photoconductive layer may be any that satisfy the requirements of xerography, e.g., metal or glass plates, paper or plates or foils made of electrically conductive resins, or plastic resin films.
  • the electroconductivity of the base material must be higher than the electroconductivity of the photo-conductive insulating layer, preferably higher than 10 ohrn/cm. If paper is to be used as a support for the photo-conductive layer, pretreatment of the paper against penetration of the coating solution is advisable, e.g.
  • Aqueous dispersions of said substances suitable for the pretreatment of the paper surface may also be used.
  • solutions of the compounds of the diphenyland triphenyl-oxazole series to be used as provided by the invention, with or without the resins, are applied to the supports in the usual manner, for example by spraying, by brushing, by direct application by means of rollers, etc., and then dried so as to produce a thin coherent homogeneous photo-conductive layer adhering on the electro-conductive support.
  • the photo-conductive layers are generally charged positively or negatively by means of a corona discharge.
  • the thus obtained charged photo-conductive layers have a light-sensitivity generally lying within the range of the long-wave 'U.V. light of about 3600 to 4200 A.U. Even very short exposure under a master to a high pressure mercury lamp will give good images.
  • the layers corresponding to the invention have, even when charged, very little sensitivity to the visible range of the spectrum.
  • the further discovery has been made that the spectral sensitivity of the photoconductive layer can be extended by means of sensitizers into Triarylmethane dyestuffs, such as Brilliant green (No. 7
  • Xanthene dyestuffs namely rhodamines, such as Rhodamine B (No. 864, page 365), Rhodamine 6 G (No. 866, page 366), Rhodamine G ex-tra (No. 865, page 366), Sulfo-rhodamine B (No. 863, page 364), and True acid eosin G (No. 870, page 368),also phthaleins, such as Eosin S (No. 883, page 375), Eosin A (No. 881, page 374), Erythrosin (No. 886, page 376), Phloxin (No. 890, page 378), Rose Bengal (No. 889, page 378), and Fluorescein (No. 880, page 373);
  • rhodamines such as Rhodamine B (No. 864, page 365), Rhodamine 6 G (No. 866, page 366), Rhodamine G ex-tra
  • Thiazine dyestuffs such as Methylene blue (No. 1038, p
  • Acridine dyestuffs such as Acridine yellow (No. 901, page 383), Acridine orange (No. 908, page 387), and Trypaflavine (No. 906, page 386);
  • the photoconductive layer has been provided with an electrostatic charge by means of, for example, a corona discharge with a charging apparatus maintained at 6000-7000 volts
  • the support e.g. paper or aluminum foil or plastic film
  • the sensitized layer is exposed to light through amasteror by episcopic or diascopic projection to form an electrostatic pattern corresponding to the master applied by causing to leak away the electrostatic charge on the areas of the photoconductive layer struck by light and then developing the electrostatic pattern by dusting over in known manner with a resin powder colored with carbon black.
  • the image that now becomes visible by the adherent particles of the resin powder can easily be wiped off. It therefore has to be fixed; it can, for example, be heated briefly, by means of an infra-red 'radiator, to about 120 C., or to whatever the baking temperature of the developer powder used may be.
  • the temperature required is less if the heat treatment is carried out in the presence of vapors of solvents such as trichloroethylene, carbon tetra-chloride or ethyl alcohol.
  • the electrostatic pattern may also be developed by means i of a liquid developer consisting of a solvent of low electroconductivity and a suspended dyestuff or pigment and/ or resin. From positive masters, positive images characterized by good contrast are produced.
  • the fixed images may be transformed in printing plates: the support, e.g. the paper or plastic film, is wiped over with a solvent' for the photoconductive layer, e.g. alcohol or acetic acid. By this treatment, the non-image areas of the layer are removed, so that the support may now be rinsed with water. Subsequently, the support is inked in known manner with greasy ink which sticks to the imaged areas. In this way positive printing plates are obtained which can be set up in long runs.
  • a solvent' for the photoconductive layer e.g. alcohol or acetic acid
  • the electrophotographic images can also be used as masters for the production of further copies of any sort of light sensitive sheets.
  • the photoconductive compounds to be used as provided by the invention are superior to the substances used hitherto, such as selenium or zinc oxide, inasmuch as the latter give cloudy layers which are not easy to be copied because solid solutions cannot be produced with such materials and only suspensions are possible.
  • the paper After drying the coated layer, the paper is given a positive electric charge by means of a corona discharge. Thereafter a latent electrostatic image of a printed book page is produced on the paper by means of an episcopic process.
  • the coated side of the paper is then treated with a developer consisting of very small glass balls melt-coated with a resin and of a very finely divided resin-carbon black mixture electrostatically adhering thereto.
  • the black resin sticks to those areas of the layer which had not been exposed to light during exposure and a positive reproduction of the book page used as an original becomes visible.
  • the copy is warmed gently and thus fixed. The image thus obtained shows good contrast.
  • the coating is applied by means of an apparatus and has a thickness of about 6 microns.
  • a corona discharge the paper thus coated is given a negative electrical charge and then placed with its coated side onto a book page printed on both sides and backed with black paper. Through the coated paper placed thereon, the book page is exposed for one second to the light of a watt incandescent lamp.
  • the electrostatic reflex image thus produced on the paper is dusted with a developer powder consisting of 100 grams of glass balls (grain size 350 to 400 microns) and 2.5 grams of a toner powder (grain size 20 to 50 microns).
  • the toner is prepared by melting together 30 grams of, polystyrol, 30 grams of a resin-modified maleic resin having a melting point at 95-105 C., a saponification number 20-25 (Beckacite K and 3 grams of a carbon 'black produced from natural gas by impingement process (Peerless Black Russ 552), whereupon the melt is ball-milled 'and sifted.
  • a positive reverse image of the book page is obtained.
  • By firmly pressing paper or a plastic film or a fabric onto the powder image obtained the image is transferred and anon-reversed image of the original becomes visible on the paper or the film or the fabric, respectively. As is.
  • the transfer of the reverse powder-image can be favorably influenced by applying an electric field to the transfer paper or the film to carry the non-reversed image. If a transparent paper or film is used, intermediate originals are obtained from which further copies can be made, e.g. by means of a diazotype process.
  • the carbon-black resin powder image is transferred from the electrophotographic layer onto the paper to form a reverse image on said paper. If the carbon-black-resin-image is thus transferred onto transparent paper or plastic film, the image obtained can be used for making further copies, e.g. on diazo printing paper.
  • benzene The solution is coated onto an aluminum foil the surface of which has been made grease-free, and is then dried.
  • an image of an original is produced on the coated foil and the image is developed by a powder-treatment and fixed by heating. Subsequently, it is transformed into a printing plate by wiping over the image side of the aluminum foil with 96% alcohol, rinsing With water and inking with greasy ink in the presence of 1% phosphoric acid.
  • a positive printing plate is obtained which may be used for printing after clamping it into an offset printing machine.
  • An electrophotographic reproduction material comprising a conductive base material coated with a thin uniform coherent photoconductive insulating layer adhering thereto including at least one compound selected from the group consisting of an organic water-insoluble resin and a sensitizing dyestuff in admixture with at least one substituted oxazole compound corresponding to the general formula:
  • R stands for a residue selected from the group consisting of hydrogen, aryl, alkenyl, alkyl, and heterocyclic groups,
  • R stands for a residue selected from the group consisting of hydrogen, alkyl, and aryl groups
  • R stands for a residue selected from the group consisting of hydrogen and an aryl group, the compound containing at least two aryl groups.
  • An electrophotographic reproduction material comprising a conductive base material coated with a thin uniform coherent photoconductive insulating layer adhering thereto including at least one compound selected from the group consisting of an organic water-insoluble resin and a sensitizing dyestutf in admixture with at least one substituted oxazole compound corresponding to the general formula:
  • R is an aminophenyl group, R is a phenyl group and R is hydrogen.
  • An electrophotographic reproduction material comprising a conductive base material coated with a thin uniform coherent photoconductive insulating layer adhering thereto including at least one compound selected from the group consisting of an organic water-insoluble resin and a sensitizing dyestuif in admixture with at least one substituted oxazole compound corresponding to the general formula:
  • R is an aminophenyl group.
  • An electrophotographic reproduction material comprising a conductive base material coated with a thin uniform coherent photoconductive insulating layer adhering thereto including at least one compound selected from the group consisting of an organic water-insoluble resin and a sensitizing dyestuif in admixture with at least one substituted oxazole compound corresponding to the general formula:
  • R is an aminophenyl group, R is a phenyl group and R is an alkyl group.
  • An electrophotographic reproduction material comprising a conductive base material coated with a thin uniform coherent photoconductive insulating layer adhering thereto including at least. one compound selected from the group consisting of an organic water-insoluble resin,
  • R R and R are phenyl groups.
  • An electrophotographic reproduction material in which the oxazole compound is 2-(4'-diethyl-aminophenyl)-5-phenyl-oxazole.
  • the oxazole compound is 2 (2 chlorophenyl) 4 (4-diethylaminophenyl)-5- phenyl-oxazole.
  • An electrophotographic reproduction material in which the oxazole compound is 2 vinyl-4-(4'-diethylarnino-phenyl)-5 -(2'-chloropheny1)- oxazole.
  • An electrophotographic reproduction process which comprises electrostatically charging a thin uniform coherent photoconductive insulating layer adherent on a conductive base material, said photoconductive layer comprising at least one substituted oXazole compound corresponding to the general formula:
  • R stands for a residue selected from the group consisting of hydrogen, aryl, alkenyl, alkyl, and heterocyclic groups
  • R stands for a residue selected from the group consisting of hydrogen, alkyl, and aryl groups
  • R stands for a residue selected from the group consisting of hydrogen and an aryl group, the compoun containing at least two aryl groups, a
  • the photo conductive insulating layer contains a water-insoluble or- V ganic resin and a dyestufi that sensitizes the layer to visible 2-(2-chlorophenyl) 4 (4-dimethyl-aminophenyl)-5- light.
  • An electrophotographic reproduction process which comprises electrostatically charging a thin uniform coherent photoconductive insulating layer adherent on a conductive base material, said photoconductive layer comprising at least one substituted oxazole compound corresponding to the general formula:
  • R is an aminophenyl group, R is a phenyl group and R is hydrogen, exposing the charged layer to a light pattern to ,leak away the electrostatic chargeon the areas struck by light and developing the remaining charged areas with an electroscopic material and fixing the image thus obtained.
  • An electrophotographic reproduction process which comprises electrostatically charging a thin uniform coherent photoconductive insulating layer adherent on a conductive base material, said photoconductive layer comprising at least one substituted oxazole compound corresponding to the general formula:
  • R is an aminophenyl group, R is a phenyl group and R 'is an alkyl group, exposing the charged layer to a light pattern to leak away the electrostatic charge on the areas struck by light and developing the remaining charged areas with an electroscopic material and fixing the image thus obtained.
  • An electrophotographic reproduction process which comprises electrostatically charging a thin uniform coherent photoconductive insulating layer adherent on a conductive base material, said photoconductive layer comprising at.least one substituted oxazol'e compound corresponding to the general formula:
  • R R and R are phenyl groups, exposing the charged layer to a light pattern to leak away the electrostatic charge on the areas struck by light anddeveloping the remaining charged areas with tan electroscopic material and fixing the image thus obtained.
  • the photoconductive layer comprises 2- (4'-diethyl-amino phenyl) -5 -phenyl-oxazole.
  • a process according to claim 11 in which the photoconductive layer comprises 2-(2-ohlorophenyl)-4 (4'-diethyl-aminophenyl) -5-p'henyl-oxazole.
  • a process according to claim 12 in which the photoconductive layer comprises 2-(2-chlorophenyl)-4- (4-diethyl-aminophenyl -5-p'henyl-oxazole.
  • a process according to claim 13 in which the photoconducti ve layer comprises 2- (.2'-ohlorophenyl)-4- (4'-diethylam-inophenyl) -5-phenyl-0Xazole.
  • a process according to claim 11 in which the photoconductiwe layer comprises 2-(.2'-chlorophenyl)-4- (4'-diethyl-aminophenyl) -5-phenyl-oxazole.
  • a process according to claim 12 in which the photoconducti've layer comprises 2-(4-dimethyl-aminophenyl)-4-(4' dimethyl-aminophenyl) 5 (2-chlorophenyl) -ox-azole.
  • a process according to claim 13 in which the photoconductive layer comprises 2(4'-di-methyl-aminophenyl)-4-(4 dimethyl-aminop-henyl) 5 (2'-chlorophenyl) -oxazole.
  • a process according to claim 11 in which the photoconducti e layer comprises 2- (2-chlor-ophenyl)-4- (4-dimethyl.am-inophenyl) 5 (4' chlorophenyl)-oxazole.
  • a process according to claim 12 in which the photoconductive layer comprises 2-(2'-chlorophenyl)-4- (4'-din1ethy1aaminophenyl)-5 (4' chlorophenyl)-oxazole.
  • a process according to claim 13 in which the photoconduct-ive layer comprises 2(2'-chlorophenyl)-4- (4-dimethyl aminopl1enyl)-5 (4' chlorophenyl)-oxazole.
  • a process according to claim 14 in which the photoconductive layer comprises 2-(2'-chlorophenyl)-4 (4'-dimethyl+aminophenyl)-5 (4' chlorophenyl)-oxazole.
  • a process according to claim 11 in which the photoconductive layer comprises 2-vinyl-4-(4'-diethylarninophenyl)-5(2-ohlorophenyl)-oxazole.
  • a process according to claim 12 in which the photoconductive layer comprises 2-vinyl-4-(4'-diethy1- aminophenyl)-5-(2'-cl1lorophenyl)-oxazole.
  • a process according to claim 13 in which the photoconducti ve layer comprises 2-vinyl-4-(4-diethylaminophenyl) -5-'(2-c hlorophenyl -oxazole.
  • a process according to claim 14 in which the photoconducti ve layer comprises 2-viny l-4-'(4'-diethylarninophenyl) -5-( 2'-ohlorophenyl) -oxa-zole'.
  • a compound having the formula R R and R are phenyl groups.
  • a photographic reproduction process which cornprises exposing an electrostatically charged photoconductive insulating layer to a light image whereby the lightstruck area is discharged, and developing the resulting electrostatic image with an electroscopic material, said layer comprising a compound having the formula:
  • R is selectedior-m the group consisting of hydrogen, an alkyl group and an aryl group; R is selected tfrom the group consisting of hydrogen and an aryl group; R is a member selected from the group consisting of hydrogen, an alkyl group, an aryl group, and a hetero- .cyclic group, wherein at least two of R R and R are aryl groups.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US834417A 1958-08-20 1959-08-18 Electrophotographic reproduction material Expired - Lifetime US3257203A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEK35572A DE1120875B (de) 1958-08-20 1958-08-20 Material fuer elektrophotographische Reproduktion

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US3257203A true US3257203A (en) 1966-06-21

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BE (1) BE581861A (fi)
CH (1) CH379280A (fi)
DE (1) DE1120875B (fi)
ES (1) ES251855A1 (fi)
FR (1) FR1232805A (fi)
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NL126440C (fi)
BE581861A (fi)
FR1232805A (fr) 1960-10-12
CH379280A (de) 1964-06-30
ES251855A1 (es) 1960-03-16
GB874634A (en) 1961-08-10
DE1120875B (de) 1961-12-28

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