US3418322A - Quinacridone dyestuffs - Google Patents

Quinacridone dyestuffs Download PDF

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US3418322A
US3418322A US370751A US37075164A US3418322A US 3418322 A US3418322 A US 3418322A US 370751 A US370751 A US 370751A US 37075164 A US37075164 A US 37075164A US 3418322 A US3418322 A US 3418322A
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solution
photoconductor
water
mixture
acid
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Tulagin Vsevolod
Robert F Coles
Richard A Miller
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3M Co
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Minnesota Mining and Manufacturing Co
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Priority to NL263729D priority Critical patent/NL263729A/xx
Priority to US3172827D priority patent/US3172827A/en
Priority to DEM48723A priority patent/DE1177005B/de
Priority to CH452161A priority patent/CH455522A/de
Priority to GB44060/63A priority patent/GB990973A/en
Priority to FR859407A priority patent/FR1290454A/fr
Priority to GB14061/61A priority patent/GB990972A/en
Priority to NO149036A priority patent/NO122384B/no
Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Priority to US370751A priority patent/US3418322A/en
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/36—Dyes with acylated amino groups
    • C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/12—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton
    • C09B47/16—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton having alkyl radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
    • C09B47/26—Amide radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B48/00—Quinacridones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/14—Benz-azabenzanthrones (anthrapyridones)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/32—1.3 azoles of the anthracene series
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B7/00—Indigoid dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B7/00—Indigoid dyes
    • C09B7/10—Bis-thionapthene indigos
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G13/00—Electrographic processes using a charge pattern
    • G03G13/01—Electrographic processes using a charge pattern for multicoloured copies
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G17/00—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process
    • G03G17/02—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process with electrolytic development
    • 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
    • G03G5/08—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being inorganic
    • G03G5/087—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being inorganic and being incorporated in an organic bonding material
    • 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
    • G03G5/09—Sensitisors or activators, e.g. dyestuffs
    • 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
    • G03G5/12—Recording members for multicolour processes
    • 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
    • Y10S534/00—Organic compounds -- part of the class 532-570 series
    • Y10S534/02—Azo compounds containing chains of eight or more carbon atoms not provided for elsewhere in this class

Definitions

  • This invention relates to new and useful permanent reproductions and their method of preparation by selectively depositing a basic nitrogen containing compound on the surface of a photoconductor.
  • An object of this invention is to disclose a method of selectively depositing basic nitrogen containing organic compounds on the surface of a photoconductor thereby producing reproductions in a fast and eicient manner.
  • Another object of this invention is to disclose a process for preparing colored reproductions by electrophotography.
  • Full colored reproductions are prepared by successively applying subtractive primary colors to the surface of the dye-sensitized photoconductor.
  • the method of making colored reproductions from subtractive primaries is described in I. S. Friedmans A History of Color Photography, American Photographic Publishing Company, Boston, Mass. (1944).
  • the tem-n dye-sensitized indicates that the photoconductor has been treated with an organic dyestuff so that radiant energy is absorbed by the dye on the surface of the photoconductor and the energy is transferred to the photoconductor thereby making the photoconductor conductive.
  • This process may be employed in various ways to prepare permanent photographic reproductions.
  • the preferred method of course is to directly deposit a basic nitrogen containing organic dyestuff directly on the photoconductor. If the basic nitrogen containing organic compound is colorless it may then be dyed or colored in a 3,418,322 Patented Dec. 24, 1968 ice subsequent step to produce a negative image, or the deposited compound may serve as a protective coating on the surface of the photoconductor and the unprotected areas dyed or modified chemically in some manner, such as by etching away the photoconductor with an acid or sol-vent. Likewise the compound deposited on the surface of the photoconductor may sufficiently modify the wetting characteristics of the photoconductive sheet. In this manner the two areas will have a differential repellency or attraction to water or oil.
  • the varying of the surface wetting characteristics of the photoconductive sheet is particularly suitable for the production of lithographie plates where the photoconductor is rendered hydrophobic by the deposited compound.
  • the structural formula of the basic nitrogen containing organic compound to be deposited from an aqueous solution in accordance with the teachings of this invention corresponds to the formula.
  • M is an organic radical
  • R and R are hydrogen or an alkyl radical containing up to 18 carbon atoms
  • m is an integer of less than 4
  • p is an integer of less than 6
  • n is an integer of less than 6.
  • a preferred class of compounds are those that contain an alkyl radical of at least 6 carbon atoms (preferably 10)
  • R is an alkyl radical of at least 6 carbon atoms (preferably l0)
  • the R radicals are alkyl radicals containing less than 6 carbon atoms.
  • the long chain alkyl radical may also be present in the radical M, as in the case of the amino-polyamides described but is preferably one or more of the R constituents.
  • the preferred class of dyestuffs falling within the above general formula is where M is an organic radical containing a chromogenic nucleus. Illustrative chromogenic nuclei are represented by the following general classes of dyestuffs:
  • colorless images may be prepared or the colorless basic nitrogen containing organic compound may be deposited in the presence of colloidal organic 'or inorganic pigments.
  • a reaction product of dimerized linoleic acid and an excess of a polyethylenamine having an amine number of about is dissolved in ethanol and acetic lacid as a one percent solution.
  • This solution may then be neutralized ⁇ at the photoconductor-cathode and thereby a colorless insoluble solid is deposited on the surface of the photoconductor.
  • the solution is mixed with colloidal titanium dioxide, neutralization and deposition of this dispersion results in the production of white images.
  • the photoconductor-cathode is some color other than white, the titanium dioxide may be deposited yas the white portions of an image. In this manner, a direct positive image is formed.
  • ⁇ Carbon black images may be formed by mixing colloidal carbon in the solution. Using this type of dispersion black images are prepared which are completely resistant to the action of light and most atmospheric conditions. As such, they represent one of the most permanent photographic elements attainable.
  • These basic nitrogen containing organic compounds are dissolved in water by the formation of a salt with an acid moiety.
  • Suitable organic acids include formic acid, acetic acid, lactic acid, levulinic acid and the like.
  • Suitable inorganic -acids include hydrochloric acid, nitric acid7 sulfurie acid and the like.
  • the final pH of these solutions is in the range of pH 2 to 7 (preferably 4.5 to 7).
  • These aqueous solutions which are substantially free 'of positive ions other than those containing the basic nitrogen-containing organic compound are employed at solution concentrations of 0.1 to by weight.
  • FIGURE 1 is a perspective view of developing apparatus useful in the practice of this invention and FLIGURE 2 is a cross-sectional view of FIGURE 1 lalong section lines 2 2.
  • Developer tray 10 is composed of a base plate 12, which also serves as an electrode, top clamping frame member 14, and an intermediate yopen frame member 16 ttorrning upstanding walls around the base plate periphery.
  • Frame member 14 and base plate 12 have cooperating, releasable clamping means 18, which draw these members toward one another when engaged to render the tray 10 water tight.
  • the open frame member 16 is composed of a nonconductor such as polyethylene, polytetrauoroethylene or polytrifluorochloroethylene and is provided with a ledge 20 for supporting electrode 22 such that an electrical current passing to electrode 22 from the base plate-electrode 12 passes through ya photoconductor sheet 24 which is interposed between the open frame member 16 and the base plate 12.
  • This photoconductor sheet 24 is composed of an electrically conductive carrier 26 which is placed in intimate contact with the base plate 12 and photoconductor particles 28.
  • a solution 32 is placed in the developer tray 10, electrode 22 is connected to the positive terminal of the direct current power source 34 and the base plate 12 is attached to the negative terminal of the power supply 34.
  • the electrical current passes through solution 32 and the photoconductive areas of the photoconductive she-et 24 resulting in image deposits 30 on the cathode-photoconductor surface.
  • FIGURE 2 In order to graphically show the photoconductor particles 28 and the image deposit 30, they have been represented in FIGURE 2 in exaggerated size.
  • a stepwise procedure for producing an image in accordance with the -teachings of this invention is as follows:
  • the negative electrode from a direct current power supply 34 is attached to the metal base plate thereby making electrical conta-ct with the conductive backing of the photoconductor sheet 24.
  • the photoconductor sheet 24 in the developing tray 10 is exposed to light in selected areas such as by focusing and projecting a photographic negative on the photoconductor sheet 24 through a light projector.
  • the electrode 22 is placed on the ledge 20 and connected to the positive terminal ofthe direct current power supply 34.
  • the solution 32 is added to the tray.
  • the electrical current is turned on so as to elect the electrolytic development.
  • the solution is poured off and the photoconductor sheet is thoroughly washed with water. Aditer suitable dark adaptation additional images may be put on the photoconductor sheet by repeating the above procedure.
  • An especially useful method for dark adaptation of the photoconductor sheet is to place it in contact with water heated to at least 100 F. which may be accomplished simultaneously with the washing by employing the hot Water as the wash water.
  • Full color reproductions may be obtained by carrying out the above procedure three times with monochromatic light.
  • a color negative is placed in a projector equipped with a photoflood lamp and a red lter is interposed between the photoflood lamp and the photoconductor sheet, preferably between the color negative and the phototlood lamp, thereby exposing the photoconductor sheet selectively to red light.
  • a cyan image is then developed on the photoconductor using a cyan dye.
  • the photoconductive paper is then washed with warm water (heated to at least F.) and dried with a stream of air.
  • the developing tray is then returned to the enlarger and a green lter is interposed between the light source and the photoconductor sheet.
  • the light intensity of the projected image, time of exposure which may be from 0.1 second to sixty seconds, and period of electrolytic development which may be from 1 to 30 seconds at a voltage of from 5 to 150 volts are varied in accordance with quality of the image required or desired and the relative effectiveness of the photoconductor surface.
  • this sheet When dry and fully dark adapted, this sheet is used to produce reproductions and had high response spectral bands at 460-465 mu, 560 mu and 660 mu.
  • N-(2- cyanoethyl)-N-decylN,N'-diethyl 1,3 propanediamine 969 g., 3.00 moles
  • the reaction mixture was stirred and refluxed for 5 hours after all the nitrile had been added and allowed to stand overnight under dry nitrogen.
  • Excess hydride was decomposed by the addition of ethyl acetate (264 g., 3.00 moles) slowly so as to produce a gentle reiiux.
  • the resulting solution was then diazotized by the rapid addition of 5 N sodium nitrite solution (40 ml.). Additional ice was added t0 keep the mixture cold and the solution treated rapidly while stirring with a solution consi-sting of 34 g. (0.09 mole) of Naphthol AS-G Supra, a product of General Aniline & Film Corp., dissolved in 750 ml. of dimethylformamide and ml. of pyridine. More ice and water were added to insure good cooling and stirring. After one-half hour the dye was completely precipitated by the addition of concentrated ammonium hydroxide (300 ml.) and the product collected by filtration. The resulting yellow dye was washed with water and ethanol and was then crystallized from ⁇ a mixture of dimethylformamide and ethanol.
  • Alpha,alphabis[4(4 decyl 8 ethyl 4,8 diazadecyl)sulfamylphenylazo] 4,4' bi-o-acetoacetoluidide was prepared by reacting the diazo prepared from N(4 decyl 8 ethyl 4,8 diazadecyl)sulfanilamide with Naphthol AS-G in a manner similar to Preparation A above.
  • the ycorresponding terephthalyl derivative was prepared in a similar manner.
  • thioindigo-7,7dicarboxylic acid (l0 g., 0.026 mole). This was heated slowly to 90-95" C. on the steam bath with stirring, and maintained at that temperature for hours. The red solid obtained by filtering the reaction mixture was washed with benzene, filtered, washed with benzene, and washed with petroleum ether to produce thioindigo- 7,7dicarbonyl chloride (10 g.).
  • 3hydroxythionaphthene-7-carboxylic -acid (0.3 mole) was dissolved in Water (l liter) containing sodium carbonate monohydrate (40 g., 0.32 mole). To this was added with stirring a solution of potassium ferricyanide (218 g., 0.66 mole) in water (700 ml.). An additional 0 amount of sodium carbonate monohydrate (40 g., 0.32 mole) was added to keep the mixture alkaline. The mixture was stirred about one and one-half hours and filtered. The filter cake was mixed with Water (700 mL), and
  • the basic nitrogen containing compounds such as are illustrated by Preparations A to L above, are dissolved in water in the presence of an acid.
  • the solution concentration and acid employed may vary.
  • the compounds are dissolved as the acetate or hydrochloride salts in 0.5 to 2% aqueous solution.
  • Illustrative solutions of the compounds shown in Preparations A to L which may be used to form colored deposits on a photoconductor sheet are as follows:
  • magenta solution The magenta dye (4 g.) from Preparation J was mixed with ethanol (40 1111.), glacial acetic acid (0.58 ml.)
  • a colorless solution suitable for 4use in the process of this invention was prepared as follows:
  • Solutions especially useful for the deposition of dye images by electrophotography are obtained by mixing this colorless solution with a dye solution. For instance, 50 g. portions of this colorless solution in admixture with 100 g. portions of solutions (a), (b) and (c) were found to be especially useful for the production of colored images.
  • This colorless stock solution can, of course, also be deposited by itself or in admixture with other pigments. For instance, white images are obtained by using the solution in admixture with dispersed titanium dioxide in the following developmental procedure. Black images are obtained using dispersed carbon particles in this solution.
  • a preferred combination of solutions for preparing a true-to-life colored reproduction are solutions (a), (b), and (c) above whereby the yellow dye [solution (c)] is deposited tirst, the magenta dye [solution (b)] is deposited second, and the cyan dye [solution (a)] is deposited third.
  • NICHOLAS S. RIZZO Primary Examiner.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Molecular Biology (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Color Printing (AREA)
  • Pyridine Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
US370751A 1960-04-18 1964-05-07 Quinacridone dyestuffs Expired - Lifetime US3418322A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
NL263729D NL263729A (no) 1960-04-18
US3172827D US3172827A (en) 1960-04-18 Permanent reproductions
DEM48723A DE1177005B (de) 1960-04-18 1961-04-17 Verfahren zur Herstellung ein- oder mehrfarbiger Reproduktionen mit Hilfe einer elektrolytischen Bildentwicklung
CH452161A CH455522A (de) 1960-04-18 1961-04-17 Verfahren zur Herstellung von Reproduktionen
GB44060/63A GB990973A (en) 1960-04-18 1961-04-18 Dyestuffs containing polyalkyleneamine groups
FR859407A FR1290454A (fr) 1960-04-18 1961-04-18 Procédé de fabrication d'images photographiques permanentes
GB14061/61A GB990972A (en) 1960-04-18 1961-04-18 Photoconductive copy sheets
NO149036A NO122384B (no) 1960-04-18 1963-06-14
US370751A US3418322A (en) 1960-04-18 1964-05-07 Quinacridone dyestuffs

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US2301760A 1960-04-18 1960-04-18
US370751A US3418322A (en) 1960-04-18 1964-05-07 Quinacridone dyestuffs

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US3418322A true US3418322A (en) 1968-12-24

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US370751A Expired - Lifetime US3418322A (en) 1960-04-18 1964-05-07 Quinacridone dyestuffs

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CH (1) CH455522A (no)
DE (1) DE1177005B (no)
FR (1) FR1290454A (no)
GB (2) GB990972A (no)
NL (1) NL263729A (no)
NO (1) NO122384B (no)

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US3753708A (en) * 1971-03-29 1973-08-21 Xerox Corp Photoelectrophoretic imaging process employing quinacridone pigments
US4310359A (en) * 1980-02-25 1982-01-12 Toyo Ink Manufacturing Co., Ltd. Pigment compositions
US4317682A (en) * 1979-08-27 1982-03-02 Toyo Ink Manufacturing Co. Ltd. Pigment compositions and use thereof
US5698024A (en) * 1996-12-31 1997-12-16 Bayer Corporation Organic pigment compositions
US5711800A (en) * 1996-12-31 1998-01-27 Bayer Corporation Organic pigment compositions
US5879444A (en) * 1997-09-02 1999-03-09 Bayer Corporation Organic pigment compositions
US5900213A (en) * 1993-04-28 1999-05-04 Alcon Laboratories, Inc. Use of diamines to disinfect and clean contact lenses and preserve ophthalmic compositions
US6066203A (en) * 1998-05-01 2000-05-23 Bayer Corporation Pigment derivatives for waterborne coatings
WO2013139006A1 (zh) * 2012-03-21 2013-09-26 大连理工大学 一类4位n取代的蒽吡啶酮荧光染料、其制备方法及应用
CN107446374A (zh) * 2017-08-01 2017-12-08 南京工业大学 一类喹吖啶酮多季铵盐衍生物及其制备方法

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DE1219328B (de) * 1961-04-19 1966-06-16 Agfa Ag Verfahren zur Entwicklung von Ladungsbildern
US3384565A (en) * 1964-07-23 1968-05-21 Xerox Corp Process of photoelectrophoretic color imaging
US3436321A (en) * 1966-09-13 1969-04-01 Minnesota Mining & Mfg Developer compositions and their use in electrolytic electrophotography
ZA6555105B (no) * 1967-08-25
US4271088A (en) 1978-06-16 1981-06-02 Suntech, Inc. High selectivity cyanoalkylation process
GB8400984D0 (en) * 1984-01-14 1984-02-15 Hepburn C Polychloroprene rubber

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US2238485A (en) * 1939-11-04 1941-04-15 Eastman Kodak Co Azo compound and material colored therewith
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US2972508A (en) * 1955-12-29 1961-02-21 Bayer Ag Dyeing of polymers of acrylonitrile
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US2756234A (en) * 1956-07-24 Anthrapyridones
US2151518A (en) * 1935-03-07 1939-03-21 Gen Aniline Works Inc Azo dyestuff
US2238485A (en) * 1939-11-04 1941-04-15 Eastman Kodak Co Azo compound and material colored therewith
US2972508A (en) * 1955-12-29 1961-02-21 Bayer Ag Dyeing of polymers of acrylonitrile
US2945849A (en) * 1957-03-04 1960-07-19 Bayer Ag Disazo compounds containing a quaternary ammonium group
US3139421A (en) * 1960-03-14 1964-06-30 Parke Davis & Co Azo compounds and methods for producing same

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3753708A (en) * 1971-03-29 1973-08-21 Xerox Corp Photoelectrophoretic imaging process employing quinacridone pigments
US4317682A (en) * 1979-08-27 1982-03-02 Toyo Ink Manufacturing Co. Ltd. Pigment compositions and use thereof
US4310359A (en) * 1980-02-25 1982-01-12 Toyo Ink Manufacturing Co., Ltd. Pigment compositions
US5900213A (en) * 1993-04-28 1999-05-04 Alcon Laboratories, Inc. Use of diamines to disinfect and clean contact lenses and preserve ophthalmic compositions
US5698024A (en) * 1996-12-31 1997-12-16 Bayer Corporation Organic pigment compositions
US5711800A (en) * 1996-12-31 1998-01-27 Bayer Corporation Organic pigment compositions
US5879444A (en) * 1997-09-02 1999-03-09 Bayer Corporation Organic pigment compositions
US6066203A (en) * 1998-05-01 2000-05-23 Bayer Corporation Pigment derivatives for waterborne coatings
WO2013139006A1 (zh) * 2012-03-21 2013-09-26 大连理工大学 一类4位n取代的蒽吡啶酮荧光染料、其制备方法及应用
CN107446374A (zh) * 2017-08-01 2017-12-08 南京工业大学 一类喹吖啶酮多季铵盐衍生物及其制备方法

Also Published As

Publication number Publication date
NO122384B (no) 1971-06-21
NL263729A (no)
DE1177005B (de) 1964-08-27
CH455522A (de) 1968-07-15
GB990973A (en) 1965-05-05
GB990972A (en) 1965-05-05
FR1290454A (fr) 1962-04-13
US3172827A (en) 1965-03-09

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