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EP0576472B1 - Toner electrostatique contenant un compose cetonique comme stabilisateur de la charge - Google Patents

Toner electrostatique contenant un compose cetonique comme stabilisateur de la charge Download PDF

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Publication number
EP0576472B1
EP0576472B1 EP92906365A EP92906365A EP0576472B1 EP 0576472 B1 EP0576472 B1 EP 0576472B1 EP 92906365 A EP92906365 A EP 92906365A EP 92906365 A EP92906365 A EP 92906365A EP 0576472 B1 EP0576472 B1 EP 0576472B1
Authority
EP
European Patent Office
Prior art keywords
formula
alkyl
phenyl
compound
electrostatic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP92906365A
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German (de)
English (en)
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EP0576472A1 (fr
Inventor
Gunter-Rudolf Schroeder
Udo Mayer
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BASF SE
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BASF SE
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Publication date
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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
    • G03G9/12—Developers with toner particles in liquid developer mixtures
    • G03G9/135—Developers with toner particles in liquid developer mixtures characterised by stabiliser or charge-controlling agents
    • 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
    • G03G9/0975—Organic compounds anionic

Definitions

  • JP-A-212 851/1986 or JP-A-212 852/1986 electrostatic toners which have metal salts of ⁇ -dicarbonyl compounds as charge stabilizers.
  • the charge stabilizer of the formula I can be in various tautomeric forms, all of which are included in the claim.
  • substituted phenyl groups occur in the abovementioned formula I, suitable substituents are, for example, C 1 -C 20 alkyl or C 1 -C 20 alkoxy.
  • the phenyl groups are generally substituted one to three times.
  • Z, R 1 , R 2 and R 3 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
  • Z, R 1 and R 2 are furthermore, for example, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, heptyl, 1-ethylpentyl, octyl, isooctyl, 2-ethylhexyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl , Isotridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl (the above terms isooctyl, isononyl, isodecyl and isotridecyl are trivial names and come from the alcohols obtained after oxosynthesis - see also Ullmanns Chemie E
  • Z and R 3 are, for example, phenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2-, 3- or 4-propylphenyl, 2-, 3- or 4-isopropylphenyl, 2-, 3- or 4-butylphenyl, 2-, 3- or 4- (2-ethylhexyl) phenyl, 2,4-dimethylphenyl, 2,4,6-trimethylphenyl, 2-, 3- or 4-methoxyphenyl, 2 -, 3- or 4-ethoxyphenyl, 2-, 3- or 4-propoxyphenyl, 2-, 3- or 4-butoxyphenyl, 2-, 3- or 4- (2-ethylhexyloxy) phenyl, 2,4-dimethoxyphenyl or 2,4,6-trimethoxyphenyl.
  • L are, for example, -CH 2 -, - (CH 2 ) 2 -, - (CH 2 ) 3 -, - (CH 2 ) 4 -, -CH (CH 3 ) -CH 2 -, -CH (CH 3 ) -CH (CH 3 ) - or CH (CH 3 ) - (CH 2 ) 2 -.
  • Suitable cations Kat ⁇ are derived, for example, from hydrogen or from a metal.
  • Electrostatic toners which contain a compound of the formula I in which ZC 1 -C 20 -alkyl or optionally substituted phenyl and X and Y independently of one another each have a radical of the formula -CO-OR 1 or -CO-R 3 , in which R 1 is C 1 -C 20 alkyl and R 3 is C 1 -C 20 alkyl or phenyl.
  • Electrostatic toners which contain a compound of the formula I in which Kat ⁇ is a proton, a lithium, sodium or potassium ion or the equivalent of a magnesium, calcium or barium ion are furthermore particularly preferred.
  • Electrostatic toners that contain mixtures of the same keto compound and different cations, in particular calcium and barium ions, are particularly noteworthy.
  • the mixing partners can be present in the mixtures in any ratio.
  • mixtures of the calcium and barium salts those with a molar ratio of calcium salt: barium salt of 1: 1 to 99: 1 should be particularly emphasized.
  • Such mixtures can be prepared either by mechanical mixing or directly during the synthesis of the salts.
  • the proportion of the charge stabilizer of the formula I in the electrostatic toner is generally 0.01 to 2% 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 and magnetically attractable material 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.
  • 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 II MeFe 2 O 4 (II), where Me is a divalent metal, for example iron, cobalt, zinc, nickel or manganese.
  • the toners containing the compounds I as charge stabilizers are prepared by customary processes, e.g. by mixing the constituents in a kneader and then pulverizing or melting the polymeric binder or a mixture of the polymeric binders, then finely dividing one or more compounds of the formula I and the other additives, if used, into the molten resin using the for 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 I 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 or the solvents evaporated and the solid residue ground into particles of the desired particle size.
  • the compounds of formula I are advantageous charge stabilizers. They generally satisfy 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 charging profile, i.e. the toners can be quickly and highly charged.
  • the charge stabilizers according to the invention furthermore ensure that the charge is kept constant at a high level.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Un toner électrostatique contient un liant polymère et, en tant que stabilisateur de la charge, un composé répondant à la formule (I), dans laquelle Z représente alkyle C1-C20, éventuellement substitué par phényle, cycloalkyle C5-C7 ou phényle éventuellement substitué; X et Y représentent cyano ou un reste répondant à la formule -CO-OR1, -CO-NR1R2 ou-CO-R?3, où R1¿ représente alkyle C¿1?-C20, éventuellement substitué par phényle, ou cycloalkyle C5-C7; R?2¿ représente hydrogène ou alkyle C¿1?-C4; et R?3¿ représente alkyle C¿1?-C20, éventuellement substitué par phényle, cycloalkyle C5-C7 ou phényle éventuellement substitué; ou bien X et Y représentent ensemble un reste répondant à la formule -CO-L-CO- ou -CO-CH=C(CH3)-O-CO-, où L représente alkylène C2-C4; et Kat?+¿ désigne l'équivalent d'un cation. L'invention concerne également l'utilisation de ces composants en tant que stabilisateurs de la charge dans des toners électrostatiques.

Claims (8)

  1. Encre électrostatique, qui contient un liant polymérique et, à titre de stabilisateur de charge, un composé de la formule I
    Figure imgb0009
     dans laquelle
    Z   représente un radical alkyle en C1 à C20, à substitution phénylique éventuelle, un radical cycloalkyle en C5 à C7, ou un radical phényle éventuellement substitué,
    X   et Y ont des significations identiques ou différentes et représentent chacun, indépendamment l'un de l'autre, un radical cyano ou un reste de la formule -CO-OR1, -CO-NR1R2 ou -CO-R3, où R1 représente un groupe alkyle en C1 à C20 à substitution phénylique éventuelle, ou un radical cycloalkyle en C5 à C7, R2 représente un atome d'hydrogène ou un radical alkyle en C1 à C4 et R3 représente un radical alkyle en C1 à C20 à substitution phénylique éventuelle, un radical cycloalkyle en C5 à C7, ou un radical phényle éventuellement substitué, ou bien X et Y représentent ensemble un reste de la formule -CO-L-CO- ou -CO-CH=C(CH3)-O-CO-, où L représente un groupe alkylène en C2 à C4 et
    cat⊕   représente l'équivalent d'un cation.
  2. Encre électrostatique suivant la revendication 1, contenant un composé de la formule I dans laquelle
    Z   représente un groupe alkyle en C1 à C20, ou un groupe phényle éventuellement substitué et
    X   et Y représentent chacun, indépendamment l'un de l'autre, un reste de la formule -CO-OR1 ou -CO-R3, où R1 représente un radical alkyle en C1 à C20 et R3 représente un radical alkyle en C1 à C20 ou un radical phényle.
  3. Encre électrostatique suivant la revendication 1, contenant un composé de la formule I dans laquelle
    cat⊕ représente un proton, un cation, qui provient d'un métal du groupe IA du système périodique des éléments, ou l'équivalent d'un cation qui provient d'un métal du groupe 2A du système périodique des éléments.
  4. Encre électrostatique suivant la revendication 1, contenant un composé de la formule I dans laquelle
    Z   représente un radical alkyle en C1 à C20,
    X   représente le reste -CO-OR1, où R1 représente un radical alkyle en C1 à C20 et
    Y   représente le reste -CO-R3, où R3 représente un radical alkyle en C1 à C20 ou un radical phényle.
  5. Encre électrostatique suivant la revendication 1, contenant un composé de la formule I dans laquelle
    cat⊕ représente un proton, un ion lithium, sodium ou potassium, ou l'équivalent d'un ion magnésium ou calcium.
  6. Encre électrostatique suivant la revendication 1, contenant 0,01 à 2% en poids, par rapport au poids de l'encre, d'un composé de la formule I.
  7. Encre électrostatique suivant la revendication 1, contenant complémentairement un colorant.
  8. Utilisation des composés de la formule I suivant la revendication 1 à titre de stabilisateurs de charge dans des encres électrostatiques.
EP92906365A 1991-03-20 1992-03-11 Toner electrostatique contenant un compose cetonique comme stabilisateur de la charge Expired - Lifetime EP0576472B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4109086 1991-03-20
DE4109086A DE4109086A1 (de) 1991-03-20 1991-03-20 Elektrostatischer toner, enthaltend eine ketoverbindung als ladungsstabilisator
PCT/EP1992/000534 WO1992016878A1 (fr) 1991-03-20 1992-03-11 Toner electrostatique contenant un compose cetonique comme stabilisateur de la charge

Publications (2)

Publication Number Publication Date
EP0576472A1 EP0576472A1 (fr) 1994-01-05
EP0576472B1 true EP0576472B1 (fr) 1996-08-28

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EP92906365A Expired - Lifetime EP0576472B1 (fr) 1991-03-20 1992-03-11 Toner electrostatique contenant un compose cetonique comme stabilisateur de la charge

Country Status (8)

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US (1) US5338639A (fr)
EP (1) EP0576472B1 (fr)
JP (1) JPH06505812A (fr)
KR (1) KR930703632A (fr)
CA (1) CA2099570A1 (fr)
DE (2) DE4109086A1 (fr)
ES (1) ES2090613T3 (fr)
WO (1) WO1992016878A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4747895B2 (ja) * 2005-06-23 2011-08-17 コニカミノルタホールディングス株式会社 金属含有化合物を用いた電子写真用トナー

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4265990A (en) * 1977-05-04 1981-05-05 Xerox Corporation Imaging system with a diamine charge transport material in a polycarbonate resin
JPS6126058A (ja) * 1984-07-17 1986-02-05 Ricoh Co Ltd 乾式電子写真トナ−
JPS61190344A (ja) * 1985-02-20 1986-08-25 Toray Ind Inc 静電写真用トナ−
JPS61212851A (ja) * 1985-03-19 1986-09-20 Canon Inc 静電荷像現像用トナ−
JPS61212852A (ja) * 1985-03-19 1986-09-20 Canon Inc 静電荷像現像用トナ−
JPS62125366A (ja) * 1985-11-27 1987-06-06 Ricoh Co Ltd 電子写真用乾式トナ−
US5153090A (en) * 1990-06-28 1992-10-06 Commtech International Management Corporation Charge directors for use in electrophotographic compositions and processes
US5028508A (en) * 1989-12-20 1991-07-02 Dximaging Metal salts of beta-diketones as charging adjuvants for electrostatic liquid developers
DE69033748T2 (de) * 1990-09-13 2001-09-20 Commtech International Management Corp., Menlo Park Eine auf solvatation basierende ladungssteuerung von elektro-photograpischen flüssigentwicklerzusammensetzungen

Also Published As

Publication number Publication date
KR930703632A (ko) 1993-11-30
EP0576472A1 (fr) 1994-01-05
CA2099570A1 (fr) 1992-09-21
DE59207011D1 (de) 1996-10-02
JPH06505812A (ja) 1994-06-30
DE4109086A1 (de) 1992-09-24
ES2090613T3 (es) 1996-10-16
WO1992016878A1 (fr) 1992-10-01
US5338639A (en) 1994-08-16

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