Classifications

• • 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
  • G03G9/087—Binders for toner particles
  • G03G9/08742—Binders for toner particles comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • G03G9/08768—Other polymers having nitrogen in the main chain, with or without oxygen or carbon only
• • 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
  • G03G9/087—Binders for toner particles
  • G03G9/08742—Binders for toner particles comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • G03G9/08766—Polyamides, e.g. polyesteramides
• • 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
  • G03G9/097—Plasticisers; Charge controlling agents
  • G03G9/09733—Organic compounds
  • G03G9/09775—Organic compounds containing atoms other than carbon, hydrogen or oxygen
• • 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
  • G03G9/087—Binders for toner particles
  • G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
  • G03G9/08793—Crosslinked polymers
• • 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
  • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
  • Y10S430/001—Electric or magnetic imagery, e.g., xerography, electrography, magnetography, etc. Process, composition, or product
  • Y10S430/105—Polymer in developer

Definitions

• the present invention relates to new electrostatic toners containing a polymeric binder and as a charge stabilizer, a polyamine whose average molecular weight is 150 to 15,000, the nitrogen atoms by C1-C13 alkylene, which is optionally substituted by phenyl, or phenylene, which is optionally substituted by C1 -C4-alkyl is substituted, separated from one another and as substituents C1-C13-alkyl, which is optionally substituted by phenyl, hydroxy or carboxyl, phenyl, C1-C10-alkanoyl, benzoyl, C1-C6-alkylcarbamoyl, phenylcarbamoyl or a radical of the formula CO-L-CO, in which L is C2-C8-alkylene, which results in the latter case crosslinking of two polyamine units, and the use of the above-mentioned polyamines as charge stabilizers in electrostatic toners.
• Latent electrostatic image recordings are developed by inductively depositing the toner on the electrostatic image.
• the charge stabilizers stabilize the electrostatic charge on the toner. This makes the picture more vivid and sharper.
• electrostatic toners which contain amines or ammonium salts as charge stabilizers.
• the object of the present invention was therefore to provide new electrostatic toners which have charge stabilizers which have advantageous performance properties.
• All alkyl and alkylene residues occurring in the polyamines can be both straight-chain and branched.
• Suitable alkyl radicals are e.g. Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, 2-methylhexyl, octyl, isooctyl, 2-ethylhexyl, nonyl, isononyl, Decyl, isodecyl, undecyl, dodecyl, tridecyl, isotridecyl, benzyl, 1- or 2-phenylethyl, 2-hydroxyethyl, 2- or 3-hydroxypropyl, 1-carboxylethyl or 2-carboxylpropyl.
• Suitable alkylene radicals are (CH2) 2, (CH2) 3, (CH2) 4, (CH2) 5, (CH2) 6, (CH2) 7, (CH2) 8, (CH2) 9, (CH2) 10, (CH2 ) 11, (CH2) 12, (CH2) 13, CH (CH3) CH2, CH (CH3) CH (CH3), CH (C6H5) CH2 or CH (C6H5) CH (C6H5).
• Suitable phenylene residues are e.g. 1,2-, 1,3- or 1,4-phenylene, 2-methyl-1,4-phenylene or 2,5-dimethyl-1,4-phenylene.
• Suitable alkanoyl residues are e.g. Formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl, isopentanoyl, hexanoyl, heptanoyl, octanoyl, 2-ethylhexanoyl, nonanoyl or decanoyl.
• Suitable alkyl carbamoyl residues are e.g. Methylcarbamoyl, ethylcarbamoyl, propylcarbamoyl, isopropylcarbamoyl, butylcarbamoyl, isobutylcarbamoyl, pentylcarbamoyl, isopentylcarbamoyl, neopentylcarbmaoyl or hexylcarbamoyl.
• Electrostatic toners containing a polyamine whose average molecular weight is 400 to 4,000 are preferred.
• electrostatic toners that contain a polyamine that has at least 3 nitrogen atoms.
• Such polyamines generally have different proportions of primary, secondary and tertiary nitrogen atoms.
• electrostatic toners containing a polyamine in which the nitrogen atoms are separated from one another by C2-C4 alkylene are also preferred.
• electrostatic toners containing a polyamine in which the nitrogen atoms have C1-C13 alkyl as a substituent are also preferred.
• Electrostatic toners which contain a polyamine in which the nitrogen atoms are separated from one another by ethylene or 1,2- or 1,3-propylene, in particular ethylene, are particularly preferred.
• electrostatic toners containing a polyamine in which the nitrogen atoms have C1-C6-alkyl as a substituent are particularly preferred.
• polyamines are generally known per se or can be obtained by methods known per se, as described in US Pat. No. 3,705,200, DE-A-2 253 594 or DE-A-2 606 823.
• alkylating substances are all substances which enter into a reaction with the NH groups of the base body and exchange for this purpose a substitutable group, e.g. Contain sulfate, halogen, hydroxy or acetate. E.g. also such substances into consideration which contain an activated double bond, such as acrylic acid or styrene, or which have a reactive group, such as an oxirane ring.
• Acylating reagents such as carboxylic acids, carboxylic acid esters or isocyanates can also be used for this purpose, since they can also substitute the primary and secondary nitrogen atoms of the base body to a greater extent.
• reagents which themselves contain substituted nitrogen atoms and can easily react with the nitrogen atoms of the base body and thereby convert the majority of the primary and secondary amine functions in the base body into tertiary amine functions.
• the corresponding polyamine base bodies can e.g. can be prepared in a manner known per se by conventional condensation, addition or substitution reactions from ammonia or amines and corresponding reactants, for example by reacting ammonia with ethylene dichloride or propylene dichloride. They can also be produced by partial acylation of the nitrogen atoms with corresponding carboxylic acids.
• Particularly preferred base bodies are those base bodies which, e.g. can be obtained by polymerizing aziridine.
• the proportion of the polyamines specified above in the electrostatic toner is usually 0.01 to 10% by weight, based on the weight of the toner.
• the polymeric binders contained in the new electrostatic toners are known per se. They are generally thermoplastic and have a softening point of 40 to 200 ° C, preferably 50 to 130 ° C and in particular 65 to 115 ° C.
• Examples of polymeric binders are polystyrene, copolymers of styrene with an acrylate or methacrylate, copolymers of styrene with butadiene and / or acrylonitrile, polyacrylates, polymethacrylates, copolymers of an acrylate or methacrylate with vinyl chloride or vinyl acetate, polyvinyl chloride, copolymers of vinyl chloride with vinylidene chloride, copolymers of Vinyl chloride with vinyl acetate, polyester resins, epoxy resins, polyamides or polyurethanes.
• the toners according to the invention can contain colorants, magnetically attractable material, waxes and flow agents in known amounts.
• the colorants can be organic dyes or pigments such as nigrosine, aniline blue, 2,9-dimethylquinacridone, C.I. Disperse Red 15 (C.I. 6010), C.I. Solvent Red 19 (C.I. 26 050), C.I. Pigment Blue 15 (C.I. 74 160), C.I. Pigment Blue 22 (C.I. 69 810) or C.I. Solvent Yellow 16 (C.I. 12 700) or inorganic pigments such as carbon black, red lead, yellow lead oxide or chrome yellow. Generally, the amount of the colorant present in the toner does not exceed 15% by weight based on the weight of the toner.
• the magnetically attractable material can be, for example, iron, nickel, chromium oxide, iron oxide or a ferrite of the formula MeFe2O4, in which Me is a divalent metal, for example iron, cobalt, zinc, nickel or manganese.
• the toners according to the invention are produced by customary processes, e.g. by mixing the constituents in a kneader and then pulverizing or by melting the polymeric binder or a mixture of the polymeric binders, then finely dividing one or more of the polyamines specified above, and the other additives, if used, into the molten resin using the Mixing and kneading machines known for this purpose, then cooling the melt to a solid mass and finally grinding the solid mass into particles of the desired particle size (generally 0.1 to 50 ⁇ m). It is also possible to suspend the polymeric binder and the charge stabilizer in a common solvent and to add the other additives to the suspension. The suspension can thus be used as a liquid toner.
• the liquid can also be spray-dried in a manner known per se, the solvents evaporated or the liquid freeze-dried and the solid residue ground into particles of the desired particle size.
• toner preparation can then be used in a xerographic imaging system, for example according to US-A-4,265,990.
• the polyamines described in more detail above are advantageous charge stabilizers. They generally meet the application profile initially mentioned and are particularly distinguished by the fact that, when added to a toner preparation, they give it a favorable electrostatic charge profile, i.e. the toners can be quickly and highly charged.
• the charge stabilizers to be used according to the invention furthermore ensure that the charge is kept constant at a high level.
• Examples H2 to H6 listed in Table 1 below were carried out analogously to Example H1.
• N N-Dibutyl-N- (2-hydroxyethyl) amine was used as the amine.
• Table 1 E.g. Polyethylene amine No. Molecular weight Amount [g] Amine amount [g] Distilled water amount [g] Discharge quantity [g] H2 860 94.5 260 18.5 314 H3 860 113.4 234 16.7 308 H4 1500 96.6 260 21.2 313 H5 1500 82.4 277.3 23.5 308 H6 430 69.6 277.3 24.4 303
• Example H 1 0.2 g of the polyamine from Example H 1 were introduced into a solution of 10 g of a non-crosslinked styrene / butyl acrylate resin in 100 ml of xylene at room temperature and then freeze-dried.
• a developer 99% by weight of a steel carrier, which had an average particle size of 100 ⁇ m, was precisely weighed out with 1% by weight of the toner and activated on a roller block over a period specified below. The electrostatic charge of the developer was then determined. About 5 g of the activated developer were filled into a hard-blowoff cell, which was electrically connected to an electrometer, in a commercial q / m meter (from Epping GmbH, Neufahrn). The mesh size of the sieves used in the measuring cell was 80 ⁇ m.
• the toner was almost completely removed from the carrier particles by a strong air flow (approx. 4,000 cm3 / min) and simultaneous suction, the latter remaining in the measuring cell.
• the charge on the carrier was registered on the electrometer. It corresponded to the amount of charging of the toner particles, but with the opposite sign. The amount of q with the opposite sign was therefore used to calculate the q / m value.
• the mass of blown-off toner was determined by weighing the measuring cell back and the electrostatic charge q / m was calculated therefrom.

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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)

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Citations (6)

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• 1993
  • 1993-05-21 DE DE4317059A patent/DE4317059A1/de not_active Withdrawn
• 1994
  • 1994-05-13 DE DE59407514T patent/DE59407514D1/de not_active Expired - Fee Related
  • 1994-05-13 EP EP94107459A patent/EP0628884B1/fr not_active Expired - Lifetime
  • 1994-05-18 US US08/245,559 patent/US5491043A/en not_active Expired - Fee Related
  • 1994-05-20 JP JP6106617A patent/JPH06348061A/ja not_active Withdrawn

Patent Citations (6)

Non-Patent Citations (3)

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