US3844815A - Foron yellow as a toner colorant - Google Patents

Foron yellow as a toner colorant Download PDF

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Publication number
US3844815A
US3844815A US00316142A US31614272A US3844815A US 3844815 A US3844815 A US 3844815A US 00316142 A US00316142 A US 00316142A US 31614272 A US31614272 A US 31614272A US 3844815 A US3844815 A US 3844815A
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Prior art keywords
toner
resin
colorant
carrier
composition
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US00316142A
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English (en)
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R Parent
J Brado
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Xerox Corp
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Xerox Corp
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Application filed by Xerox Corp filed Critical Xerox Corp
Priority to US00316142A priority Critical patent/US3844815A/en
Priority to CA186,430A priority patent/CA1003264A/en
Priority to BR9798/73A priority patent/BR7309798D0/pt
Priority to NL7317283A priority patent/NL7317283A/xx
Priority to IT3036/73A priority patent/IT1000870B/it
Priority to FR7345058A priority patent/FR2210781B1/fr
Priority to DE2362666A priority patent/DE2362666A1/de
Priority to AU63758/73A priority patent/AU6375873A/en
Priority to JP48141773A priority patent/JPS4991232A/ja
Priority to BE138971A priority patent/BE808754A/xx
Application granted granted Critical
Publication of US3844815A publication Critical patent/US3844815A/en
Anticipated expiration legal-status Critical
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/10—Developers with toner particles characterised by carrier particles
    • G03G9/113—Developers with toner particles characterised by carrier particles having coatings applied thereto
    • G03G9/1132—Macromolecular components of coatings
    • G03G9/1133—Macromolecular components of coatings obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/09—Colouring agents for toner particles
    • G03G9/0906—Organic dyes

Definitions

  • ABSTRACT A dye colorant for use in electrophotography as a toner material is disclosed. Such dye toner systems are found to have excellent tinctorial strength and triboelectric properties among others, which render them extremely suitable for use in electrophotographic imaging processes. These toners alone and in combination with carriers as developers as employed in electrophotographic processes are also disclosed.
  • Electrostatography that branch of the imaging art which relates to the formation and utilization of latent electrostatic charge patterns to record and reproduce patterns in visible form is well known in the art.
  • this imaging method is referred to as electrophotography and more commonly known as xerography, the basic techniques of which are disclosed in U.S. Pat. No. 2,297,691.
  • the latent electrostatic images thus formed may be developed or rendered visible by deposition of a finely divided electroscopic material referred to in the art as toner.
  • the image thus obtained may be utilized in a number of ways, for example, the image may be fused or fixed in place or transferred and then fixed to a second surface.
  • Electrography the other broad general branch of electrostatography, generally divided into two broad sectors which are referred to as xeroprinting and electrographic or TESl recording, does not employ a photoresponsive medium, the charging and selective discharging thereof to form its latent electrostatic image.
  • Xeroprinting the electrostatic analog of ordinary printing, is more fully described in U.S. Pat. No. 2,576,047 to Schaffert.
  • TESl imaging or transfer of electrostatic images more fully described in U.S. Pat. No. 2,285,814, involves the formation of an electrostatic charge pattern conforming to a desired reproduction on a uniform insulating layer by means of an electrical discharge between two or more electrodes on opposite sides of the insulating medium.
  • the lines of force generated by the latent electrostatic image are employed to control the deposition of the toner material to form an image.
  • Various developers both powder and liquid and developing systems are well known to those skilled in the art including cascade development as disclosed in U.S. Pat. No. 2,618,552 to E. N.
  • any of the electrostatographic recording systems at least three different latent electrostatic images must be formed, developed with different color toners and combined to form the final image.
  • an electrostatic latent image resulting from exposure to a first primary color may be formed on the photoconductive layer developed with a toner complementary to the primary color.
  • succeeding developments of electrostatic latent images corresponding to primary colors are accomplished with complementary toners.
  • the toner is the complement of the radiation of exposure.
  • inorganic pigments are used as the coloring material either in printing inks or electrophotographic toners since it is difficult to achieve proper color balance and saturation while at the same time keeping the colors transparent.
  • inorganic pigments the range of colors available is relatively narrow and these pigments are found to impart opacity to the materials to which they are added even in relatively small amounts.
  • Bartoszewicz et al in U.S. Pat. No. 3,345,293 teaches colored electrophotographic toners comprising substantially transparent resin particles containing organic dye pigments. These materials are stated to be advantageous in their use over prior art materials in that they are more resistant to bleeding of color upon toner fusing and they are specifically adaptable for use in three color electrophotographic processes since their colors are yellow, cyan, magenta, and their mixtures in pairs produce blue, red, and green while the three toners together produce a black. Notwithstanding the apparent advantages of the Bartoszewicz et al toners, there are nevertheless disadvantages connected with these specific toners, specifically in the case of the yellow toner when employed in an automatic electrophotographic machine.
  • the yellow colorant as advanced by Bartoszewicz, et al consists essentially of from about 0.92 to about 1.08 parts by weight of 3,3'-dichloro, 4'-bis(2"- acetyl-2"-azo-o-acetotoluidide)biphenyl per 10 parts by weight of a substantially transparent resin.
  • the problems in employing this colorant reside in its inability to disperse substantially uniformly in transparent resin materials and more significantly the undesirable triboelectric properties which result from its use causing poor images of low contrast and low machine life.
  • Another object of this invention is to provide a dye colorant to be used in combination with a resin material as a toner for use in color imaging.
  • Still another object of this invention is to provide a novel electrostatographic dye'toner system.
  • Yet still another object of this invention is to provide a novel, transparent dye toner which may be employed in a trichromatic color synthesis of either the additive or subtractive color formation types.
  • Another object of this invention is to provide a novel electrographic developer.
  • Yet still another object of this invention is to provide a novel dye-toner material which possesses superior triboelectric properties and results in superior reproduction and long machine life.
  • Another object of this invention is to provide a novel dye toner wherein the dye colorant disperses substantially uniformly in a resin material.
  • a further object of this invention is to provide a relatively pure yellow toner of a desirable shade and tone.
  • a still further object of this invention is to provide an electrophotographic process employing a novel yellow dye-toner system.
  • Still a further object of this invention is to provide an electrophotographic process employing a novel orange dye-toner system.
  • aryl groups both substituted and unsubstituted, CN, OH, Nl l NHCH and other mono and disubstituted alkyl and aryl substituted amines, SO NH SO Nl-l--CH and other mono and disubstituted alkyl and aryl sulfonamides, COOl-l, COOC1-l and other alkyl and aryl esters.
  • a dye of this type known as Foron Yellow, classified in the Color Index as Cl Disperse Yellow 33 having the structure may be produced employing any suitable technique. For example, a one-step condensation of aniline with 4-chloro-3nitrobenzenesulfonamide may be performed, the reaction generally being carried out at elevated temperatures in an aqueous system containing an acid binding agent to pick up the hydrochloric acid formed. The reaction proceeds as follows:
  • Disperse Yellow 42 C1 Color Index
  • Disperse Yellow 14 CI 10340 (synthesized as indicated in U.S. Pat. No. 1,618,415); Disperse Yellow 1 C1 10345 (the synthesis for which appears in U.S. Pat. No.
  • SRA Fast Golden Yellow X11 Cl 10336 prepared through a condensation of parachloroaniline and l-chloro-2-nitrobenzene; Disperse Yellow 26, SRA Fast Yellow X CI 10348 prepared by condensing aniline and 1,4-dichloro-2-nitrobenzene; Disperse Orange 15 CI 10350 (prepared as in U.S. Pat. No. 1,618,415); Disperse Yellow 9 Cl 10375 (prepared as in U.S. Pat. No. 1,618,415); Cellete Brown R CI 10390 prepared by condensing N-(P-aminophenyl)-N- methyltaurine with one chloro-2,4,6-trinitrobenzene,
  • Thermal plastics are desirable with melting points significantly above room temperature, but below that of which ordinary paper tends to char so that once the toner images form thereon or transfer to a paper copy sheet, it may be fused in place by subjecting it to heat.
  • higher melting resins may be employed and fixed to paper copy sheets by other techniques, such as subjecting the paper copy sheet bearing the powder image to vapors of a solvent for the resin as generally described in US. Pat. No. 2,776,907.
  • the resins selected should desirably have good triboelectric properties and have sufficient insulating properties to hold charge so that they may be employed in a number of development systems.
  • any suitable transparent resin possessing the properties as above described may be employed in the system of the present invention, particularly good results are obtained with the use of vinyl resins and polymeric esterification products of a dicarboxylic acid and a diol comprising a diphenol.
  • Any suitable vinyl resin may be employed in the toners of the present system including homopolymers or copolymers of two or more vinyl monomers.
  • Typical such vinyl monomeric units include: styrene; p-chlorostyrene; vinyl naphthalene; ethylenecally unsaturated mono-oletins such as ethylene, propylene, butylene, isobutylene, and the like; vinyl esters such as vinyl chloride, vinyl bromide, vinyl fluoride, vinyl acetate, vinyl propionate, vinyl benzoate, vinyl butyrate and the like; esters of alphamethylene aliphatic monocarboxylic acids such as methyl acrylate, ethyl acrylatc, n-butylacrylate, isobutyl acrylate, dodecyl acrylate, n-octyl acrylate, 2-chloroethyl acrylate, phenyl acrylate, methyl-alpha-chloroacrylate, methyl methacrylate, ethyl metchacrylate, butyl methacrylate, and the like; acrylonitri-me
  • toner resins containing a relatively high percentage of styrene are preferred since greater image definition and density is obtained with their use.
  • the styrene resin employed may be a homopolymer of styrene or styrene homologs or copolymers of styrene with other monomeric groups containing a single methylene group attached to a carbon atom by a double bond. Any of the above typical monomeric units may be copolymerized with styrene by addition polymerization.
  • Styrene resins may also be formed by the polymerization of mixtures of two or more unsaturated monomeric materials with a styrene monomer.
  • the addition polymerization technique employed embraces known polymerization techniques such as free radical, anionic and cationic polymerization processes. Any of these vinyl resins may be blended with one or more other resins if desired, preferably other vinyl resins which insure good triboelectric stability and uniform resistance against physical degradation. However, non-vinyl type thermoplastic resins may also be employed including rosin modified phenol formaldehyde resins, oil modified epoxy resins, polyurethane resins, cellulosic resins, polyetherresins, and mixtures thereof.
  • Polymeric esterification products of a dicarboxylic acid and a diol comprising a diphenol may also be used as a preferred resin material for the toner compositions of the instant invention.
  • the diphenol reactant has the general formula:
  • R represents substituted and unsubstituted alkylene radicals having from 2 to 12 carbon atoms, alkylidene radicals having from 1 to 12 carbon atoms and cycloalkylidene radicals having from 3 to 12 carbon atoms;
  • R and R" represent substituted and unsubstituted alkylene radicals having from 2 to 12 carbon atoms, alkylene arylene radicals having from 8 to 12 carbon atoms and arylene radicals;
  • X and X represent hydrogen or an alkyl radical having from 1 to 4 carbon atoms; and n; and n are each at least I and the average sum of n, and n is less than 21.
  • Diphenols wherein R represents an alkylidene radical having from 2 to 4 carbon atoms and R and R represent an alkylene radical having from 3 to 4 carbon atoms are preferred because greater blocking resistance, increased definition of xerographic characters and more complete transfer of toner images are achieved.
  • Optimum results are obtained with diols in which R is a isopropylidene radical and R and R" are selected from the group consisting of propylene and butylene radicals because the resins formed from these diols possess higher agglomeration resistance and penetrate extremely rapidly into paper receiving sheets under fusing conditions.
  • Dicarboxylic acids having from 3 to 5 carbon atoms are preferred because the resulting toner resin possesses greater resistance to film formation on reusable imaging surfaces and resist the formation of fines under machine operation conditions.
  • Optimum results are obtained with alpha unsaturated dicarboxylic acids including fumaric acid, maleic acid, or maleic acid anhydride because maximum resistance to physical degradation of the toner as well as rapid melting properties are achieved. Any suitable diphenol which satisfies the above formula may be employed.
  • Typical such diphenols include: 2,2-bis(4-beta hydroxy ethoxy phenyl)-propane, 2,2-bis(4-hydroxy isopropoxy phenyl) propane, 2,2- bis(4-beta hydroxy ethoxy phenyl) pentane, 2,2-bis(4- beta hydroxy ethoxy phenyl)-butane, 2,2-bis(4- hydroxy-propoxy-phenyl)-propane, 2,2-bis(4-hydroxypropoxy-phenyl)propane, l ,l-bis(4-hydroxy-ethoxyphenyl)-butane, l,l-bis (4-hydroxy isopropoxyphenyl) heptane, 2,2-bis(3-methyl-4-beta-hydroxy ethoxy-phenyl) propane, l,1-bis(4-beta hydroxy ethoxy phenyl)-cyclohexane, 2,2-bis(4-beta hydroxy e
  • Diphenols wherein R represents an alkylidene radical having from 2 to 4 carbon atoms and R and R" represent an alkylene radical having from 3 to 4 carbon atoms are preferred because greater blocking resistance, increased definition of xerographic characters and more complete transfer of toner images are achieved.
  • Optimum results are obtained with diols in which R is isopropylidene and R and R" are selected from the group consisting of propylene and butylene because the resins formed from these diols possess higher agglomeration resistance and penetrate extremely rapidly into paper receiving sheets under fusing conditions.
  • any suitable dicarboxylic acid may be reacted with a diol as described above to form the toner compositions of this invention either substituted or unsubstituted, saturated or unsaturated, having the general formula:
  • R represents a substituted or unsubstituted alkylene radical having from 1 to 12 carbon atoms, ar ylene radicals or alkylene arylene radicals having from 10 to 12 carbon atoms and n is less than 2.
  • Typical such dicarboxylic acids including their existing anhydrides are: oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, mesaconic acid, homophthalic acid, isophthalic acid, terephthalic acid, o-phenyleneacetic-beta-propionic acid, itaconic acid, maleic acid, maleic acid anhydride, fumaric acid, phthalic acid anhydride, traumatic acid, citraconic acid, and the like.
  • Dicarboxylic acids having from 3 to 5 carbon atoms are preferred because the resulting toner resins possess greater resistance to film formation on reusable imaging surfaces and resist the formation of fines under machine operation conditions.
  • Optimum results are obtained with alpha unsaturated dicarboxylic acids including fumaric acid, maleic acid, or maleic acid anhydride because maximum resistance to physical degradation of the toner as well as rapid melting properties are achieved.
  • the polymerization esterification products may themselves be copolymerized or blended with one or more other thermoplastic resins preferably aromatic resins, aliphatic resins, or mixtures thereof.
  • thermoplastic resins include: rosin modified phenol formaldehyde resins, oil modified epoxy resins, polyurethane resins, cellulosic resins, vinyl type resins, and mixtures thereof.
  • the added component should be present in an amount less than about 50 percent by weight based on the total weight of the resin present in the toner.
  • a relatively high percentage of the polymeric diol and dicarboxylic acid condensation product in the resinous component of the toner is preferred because a greater reduction of fusing temperatures is achieved with a given quantity of additive material. Further, sharper images and denser images are obtained when a high percentage of the polymeric diol and dicarboxylic acid condensation product is present in the toner.
  • Any suitable blending technique such as hot melt, solvent, and emulsion techniques may be employed to incorporate the added resin into'the toner mixture.
  • the resulting resin blend is substantially homogeneous and highly compatible with pigments and dyes.
  • the colorant may be added prior to, simultaneously with, or subsequent to the blending or polymerization step.
  • styrene-butyl methacrylate copolymers styrenevinyltoluene copolymers
  • styrene-acrylate copolymers polystyrene resins, predominately styrene or polystyrene based resins as generally described in Reissue Pat. No. 25,l36 to Carlson. and polystyrene blends as described in Pat. No. 2,788,288 to Rheinfrank and Jones.
  • Any well-known toner mixing and comminution technique may be employed to provide the toner compositions of the instant invention.
  • the ingredients may be thoroughly mixed by blending and milling and thereafter micropulverized.
  • spray drying a suspension of the ingredients, a hot melt or a solution of the toner composition may also be employed.
  • the carrier particles employed may be electrically conductive, insulating, magnetic or nonmagnetic, as long as the carrier particles are capable of triboelectrically obtaining a charge of opposite polarity to that of the toner particles so that the toner particles adhere to and surround the carrier particles.
  • the carrier particle is selected so that the toner particles acquire a charge having a polarity opposite to that of the electrostatic latent image so that toner deposition occurs in image areas.
  • the carriers are selected so that the toner particles acquire a charge having the same polarity as that of the electrostatic latent image resulting in toner deposition in the non-image areas.
  • Typical carrier materials include: sodium chloride, ammonium chloride, aluminium potassium chloride, Rochelle salt, sodium nitrate, aluminum nitrate, potassium chlorate, granular zircon, granular silicon, methyl methacrylate, glass, silicon dioxide, flintshot, iron, steel, ferrite, nickel, carborundum, and the like.
  • the carriers may be employed with or without a coating. Many of the foregoing and typical carriers are described by L. E. Walkup in Pat. No.
  • the electrostatic latent images developed by the toner compositions of the instant invention may reside on any surface capable of retaining charge.
  • a photoconductive member is employed to form the electrostatic latent image.
  • the photoconductive layer may comprise an inorganic or an organic photoconductive material.
  • Typical inorganic materials include: sulfur, selenium, zinc sulfide, iincb xide'fzinc cadmium sulfide, zinc magnesium ox ide, cadmium selenide, zinc silicate, calcium strontium sulfide, cadmium sulfide, mercuric iodide, mercuric oxide, mercuric sulfide, indium trisulfide, gallium selenide, arsenic disulfide, arsenic trisulfide, arsenic triselenide, antimony trisulfide, cadmium sulfo-selenide, and mixtures thereof.
  • Typical organic photoconductors include: triphenylamine', 2,4-bis(4,4-diethylaminophenol)-l ,3 ,4-oxadiazol; N-isopropylcarbazole; triphenylpyrrol; 4,5-diphenylimidazolidinone; 4,5-
  • diphenylimidazolidinethione 4,5-bis'(4'-aminophenyl)-imidazolidinone; l,5-dicyanonaphthalene; 1,4- dicyanonaphthalene; aminophthalodinitrile; nitrophthalodinitrile; 1,2,5 ,6-tetraazacyclooctatetraene- (2,4,6,8 2-mercaptobenzothiazole-2-phenyl-4- diphenylidene-oxazolone; 6-hydroxy-2,3-di(pmethoxy-phenyl)-benzofurane; benzylidene-benzhydrazide; 3-benzylidene-aminocarbazole; polyvinyl carbazole; (2-nitro-benzylidene)- p-bromo-aniline; 2,4-diphenyl-quinazoline; 1,2,4- triazine; l,5-diphenyl-3-methyl-pyrazoline; 2-(4- dimethyl
  • Typical charging methods include charge deposition resulting from air breakdown in the gap commonly referred to as TESI or charging in vacuo with an electron gun.
  • Any suitable method of exposure may be employed in the process of the instant invention.
  • Typical methods of exposure include: reflex, contact, holographic techniques, nonlens slit scanning systems, and optical projection systems involving lens imaging of opaquereflection subjects as well as transparent film originals.
  • Typical development systems include: cascade development, magnetic brush development, powder cloud development, and liquid development.
  • Any suitable method of fixing may be employed in the process of the instant invention.
  • Typical methods of fixing include: heat-pressure fusing, radiant fusing, combination radiant, conductive and convention fusing, cold pressure fixing, and flash fusing.
  • EXAMPLE 1 A 5 percent by weight mixture of Cl Disperse Yellow 33 in styrene butylmethacrylate copolymeric resin is prepared in a drum tumbler for 1 hour at about 12 RPM. The material is then poured into a vibra-screw feeder and extruded when machine equilibrium is established. The extruded strands are taken up at the rate of 60 feet per minute and cooled in a water bath at about 120F followed by forced air drying. Pellets of one-sixteenth to one-eighth inch in diameter are then jetted to about 15 microns average particle size. This toner material is then combined with a methyl terpolymer coated steel bead carrier as described by .lacknow, et al., in Pat. No.
  • Example 1 4-dimethylamino- EXAMPLE Ill
  • Disperse Yellow 42 Cl 10338 is employed at 6 percent concentration as the colorant.
  • Example IV The process as outlined in Example 1 is again performed with the exception that a 4 percent concentration of Disperse Yellow 14 CI 10340 is employed as the colorant.
  • EXAMPLE V The procedure as employed in Example 1 is again performed with the exception that 3 percent of SRA .Fast Golden Yellow X1 1 CI 10336 is employed as the colorant.
  • EXAMPLE V1 EXAMPLE Vll
  • the procedure as outlined in Example l is again performed with the exception that Cellete Brown R Cl 10390 is employed as the colorant at a concentration of 6 percent.
  • An electrostatographic developer composition comprising a carrier, a resin tone and a dye colorant, said dye colorant being substantially dispersed throughout said toner and said dye colorant comprising a compound satisfying the following formula:
  • aryl groups both substituted and unsubstituted, CN, OH, NH NHCH and other mono and disubstituted alkyl and aryl substituted amines, SO NH SO NHCH and other mono and disubstituted alkyl and aryl sulfonamides, COOH, COOCH and other alkyl and aryl esters.
  • composition as defined in claim 1 wherein said resin is a member selected from styrenebutyl methacrylate copolymers, styrene-vinyltoluene copolymers, styrene-acrylate copolymers, or poly styrene resins.
  • composition as defined in claim 1 wherein said resin comprises a polymeric esterifieation product of a dicarboxylic acid and a diol comprising a diphenol.
  • composition as defined in claim 1 wherein said resin is a styrene-butyl methacrylate copolymer.
  • composition as defined in claim 1 wherein said carrier is a methyl terpolymer coated carrier head.
  • An electrostatographic developer composition comprising a carrier, a resin toner and a dye colorant, said dye colorant being substantially dispersed throughout said toner and said colorant comprising a yellow dye satisfying the formula:
  • composition as defined in claim 8 wherein said resin is a styrene butyl methacrylate copolymer.
  • An electrostatographic imaging process comprising establishing an electrostatic latent image on a sur face and contacting said surface with a powder electrostatographic developer comprising a carrier, a resin toner and a dye colorant, said dye colorant being susbstantially dispersed throughout said toner and said colorant satisfying the formula:

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Developing Agents For Electrophotography (AREA)
US00316142A 1972-12-18 1972-12-18 Foron yellow as a toner colorant Expired - Lifetime US3844815A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
US00316142A US3844815A (en) 1972-12-18 1972-12-18 Foron yellow as a toner colorant
CA186,430A CA1003264A (en) 1972-12-18 1973-11-21 Foron yellow as a toner colorant
BR9798/73A BR7309798D0 (pt) 1972-12-18 1973-12-14 Material eletrostatografico aperfeicoado e processo aperfeicoado para a formacao de imagem e eletrostatografica
IT3036/73A IT1000870B (it) 1972-12-18 1973-12-17 Materiale elettrostatografico perfezionato
NL7317283A NL7317283A (enrdf_load_stackoverflow) 1972-12-18 1973-12-17
FR7345058A FR2210781B1 (enrdf_load_stackoverflow) 1972-12-18 1973-12-17
DE2362666A DE2362666A1 (de) 1972-12-18 1973-12-17 Elektrostatographisches material
AU63758/73A AU6375873A (en) 1972-12-18 1973-12-18 Foron yellow as a tonor colorant
JP48141773A JPS4991232A (enrdf_load_stackoverflow) 1972-12-18 1973-12-18
BE138971A BE808754A (fr) 1972-12-18 1973-12-18 Materiau de developpement electrostatographique contenant un colorant

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JP (1) JPS4991232A (enrdf_load_stackoverflow)
AU (1) AU6375873A (enrdf_load_stackoverflow)
BE (1) BE808754A (enrdf_load_stackoverflow)
BR (1) BR7309798D0 (enrdf_load_stackoverflow)
CA (1) CA1003264A (enrdf_load_stackoverflow)
DE (1) DE2362666A1 (enrdf_load_stackoverflow)
FR (1) FR2210781B1 (enrdf_load_stackoverflow)
IT (1) IT1000870B (enrdf_load_stackoverflow)
NL (1) NL7317283A (enrdf_load_stackoverflow)

Cited By (3)

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Publication number Priority date Publication date Assignee Title
US3980576A (en) * 1975-01-10 1976-09-14 Pitney-Bowes, Inc. Solid toner compositions as used in development powders
US3998747A (en) * 1973-10-02 1976-12-21 Canon Kabushiki Kaisha Color toner for electrophotography
US4126565A (en) * 1976-12-27 1978-11-21 Xerox Corporation Toners for color flash fusers containing a permanent colorant and a heat sensitive dye

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57130043A (en) * 1981-02-06 1982-08-12 Canon Inc Yellow toner

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US1059571A (en) * 1912-07-23 1913-04-22 Hoechst Ag Yellow to brown wool-dyestuffs and process of making same.
US1618415A (en) * 1924-04-04 1927-02-22 American Cellulose And Chemica Dyeing materials comprising cellulose acetate and products produced
US3345293A (en) * 1963-09-03 1967-10-03 Xerox Corp Colored electrostatographic toners containing organic dye pigments
US3594110A (en) * 1967-02-28 1971-07-20 Hoechst Ag Process for dyeing shaped acrylonitrile copolymerizates

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BE594397A (enrdf_load_stackoverflow) * 1959-09-04
US3326848A (en) * 1964-07-02 1967-06-20 Xerox Corp Spray dried latex toners

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
US1059571A (en) * 1912-07-23 1913-04-22 Hoechst Ag Yellow to brown wool-dyestuffs and process of making same.
US1618415A (en) * 1924-04-04 1927-02-22 American Cellulose And Chemica Dyeing materials comprising cellulose acetate and products produced
US3345293A (en) * 1963-09-03 1967-10-03 Xerox Corp Colored electrostatographic toners containing organic dye pigments
US3594110A (en) * 1967-02-28 1971-07-20 Hoechst Ag Process for dyeing shaped acrylonitrile copolymerizates

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Title
Colour Index, Third Edition, Vol. 2, pgs. 2483, 2491, 2502. *
Modern Plastics Encyclopedia, 1965, pgs. 417 424, Coloring Plastics, by Simpson. *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3998747A (en) * 1973-10-02 1976-12-21 Canon Kabushiki Kaisha Color toner for electrophotography
US3980576A (en) * 1975-01-10 1976-09-14 Pitney-Bowes, Inc. Solid toner compositions as used in development powders
US4126565A (en) * 1976-12-27 1978-11-21 Xerox Corporation Toners for color flash fusers containing a permanent colorant and a heat sensitive dye

Also Published As

Publication number Publication date
AU6375873A (en) 1975-06-19
DE2362666A1 (de) 1974-06-20
CA1003264A (en) 1977-01-11
FR2210781B1 (enrdf_load_stackoverflow) 1976-11-19
IT1000870B (it) 1976-04-10
BR7309798D0 (pt) 1974-09-05
NL7317283A (enrdf_load_stackoverflow) 1974-06-20
JPS4991232A (enrdf_load_stackoverflow) 1974-08-31
FR2210781A1 (enrdf_load_stackoverflow) 1974-07-12
BE808754A (fr) 1974-04-16

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