WO1994011789A1 - Toner electrostatique renfermant des cristaux liquides amphiphiles - Google Patents

Toner electrostatique renfermant des cristaux liquides amphiphiles Download PDF

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Publication number
WO1994011789A1
WO1994011789A1 PCT/EP1993/003020 EP9303020W WO9411789A1 WO 1994011789 A1 WO1994011789 A1 WO 1994011789A1 EP 9303020 W EP9303020 W EP 9303020W WO 9411789 A1 WO9411789 A1 WO 9411789A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
electrostatic
charge
alkylene
Prior art date
Application number
PCT/EP1993/003020
Other languages
German (de)
English (en)
Inventor
Peter Neumann
Claudia Kraeh
Karin Heidrun Beck
Original Assignee
Basf Aktiengesellschaft
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to JP6511657A priority Critical patent/JPH08503083A/ja
Priority to EP93924082A priority patent/EP0671026A1/fr
Publication of WO1994011789A1 publication Critical patent/WO1994011789A1/fr

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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
    • G03G9/097—Plasticisers; Charge controlling agents
    • G03G9/09733—Organic compounds
    • G03G9/09758—Organic compounds comprising a heterocyclic ring
    • 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
    • G03G9/09741—Organic compounds cationic

Definitions

  • the present invention relates to new electrostatic toners containing a polymeric binder and a charge of a compound of formula I as a charge stabilizer
  • Q is a 2- to 6-valent radical which is derived from benzene, cyclohexane, naphthalene, triphenylene or perylene,
  • X is a chemical bond, oxygen, sulfur, sulfonyl, carbonyl or a radical of the formula O-CO, CO-O, NH-CO or CO-NH,
  • R 1 , R 2 and R 3 independently of one another are each C 1 -C 4 -alkyl, C 5 -C -cycloalkyl or R 1 and R 2 together 1,4-butylene, 1,5-pentylene or 1,5- ( 3-0xapentylene) or the rest
  • n ⁇ ö is the equivalent of an anion
  • 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 image more vivid and sharper.
  • the charge stabilizers used must meet a wide range of requirements:
  • US Pat. No. 4,851,561 discloses electrostatic toners which have benzyldimethylalkylammonium salts as charge stabilizers, with 3,5-dimethoxycarbonylbenzenesulfonate as the anion.
  • the object of the present invention was therefore to provide new electrostatic toners which have charge stabilizers and which have advantageous application properties.
  • Suitable radicals L and L 2 are, for example, (CH 2 ) 3 , (CH 2 ) 4 , (CH 2 ) 5 , ⁇ CE 2 ) 6 ,
  • L 1 are, for example, (CH 2 ) 2 , (CH 2 ) 3 or CH (CH 3 ) CH.
  • L 2 radicals are furthermore, for example, (CH 2 ) 2 .
  • R 1 , R 2 and R 3 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, cyclopentyl, cyclohexyl or cycloheptyl.
  • Suitable anions based on the equivalent of an anion (An) are, for example, halide ions such as chloride, bromide or iodide, cyanide, thiocyanate, tetrafluoroborate, methanesulfonate,
  • Electrostatic toners containing a compound of the formula I in which n is 2 or 4 and Q are a 2 or 4-valent radical which is derived from benzene are preferred.
  • Electrostatic toners containing a compound of the formula I in which L is unbranched C 3 -C 2 o-alkylene are particularly noteworthy.
  • amphiphilic liquid crystals of the formula I are known per se and are described, for example, in EP-A-199 211. They are manufactured using the methods mentioned there.
  • the proportion of the compounds of the formula I in the electrostatic toner is generally from 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 MeFe 2 0 4 , 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, for example 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 compounds of the formula I , and the other additives, if USAGE ⁇ det, in the molten resin using methods known for this purpose, mixing and kneading machines, subsequent cooling of the melt to a solid mass, and finally grinding the solid mass to give particles of the desired particle size (usually 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 obtained in this way can then be used in a xerographic image recording system, for example in accordance with US Pat. No. 4,265,990.
  • the compounds of formula I mentioned above 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 to be used according to the invention furthermore ensure that the charge is kept constant at a high level.
  • REPLACEMENT LEAF Pressure distilled off.
  • the residue was taken up in methyl tert-butyl ether, filtered and the ether solution was shaken out with 0.1 N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and water. After drying with magnesium sulfate, the solvent was distilled off.
  • Example H 2 0.2 g of the compound from Example H 2 were introduced into a solution of 10 g of an uncrosslinked styrene / butyl acrylate resin in 100 ml of p-xylene at room temperature and then freeze-dried.
  • the toner was prepared either by freeze-drying according to Example AI (marked “G” in the table) or by kneading at a temperature above the softening point of the resin according to Example A2 (in the table with "K” marked).

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

Abstract

Toner électrostatique renfermant un liant polymère et, comme stabilisateur de charge, un composé de formule (I) dans laquelle n est compris entre 2 et 6, Q est un reste bivalent à hexavalent, dérivant du benzole, du cyclohexane, de la naphtaline, du triphénylène ou du pérylène, X désigne une liaison chimique, un oxygène, soufre, sulfonyle, carbonyle ou un reste de formule O-CO, CO-O, NH-CO ou CO-NH, L est un chaînon formant un pont, R?1, R2 et R3¿ désignent un alkyle en C¿1?-C4, un cycloalkyle en C5-C7, ou bien R?1 et R2¿ représentent, conjointement, le 1,4-butylène, le 1,5-pentylène ou le 1,5-(3-oxapentylène) ou le reste pyridinium ou 3-carboxylpyridinium, et An-O est l'équivalent d'un anion. L'invention concerne également l'utilisation des composés précités comme stabilisateurs de charge dans des toners électrostatiques.
PCT/EP1993/003020 1992-11-07 1993-10-29 Toner electrostatique renfermant des cristaux liquides amphiphiles WO1994011789A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP6511657A JPH08503083A (ja) 1992-11-07 1993-10-29 両親媒性液晶を含有する静電トナー
EP93924082A EP0671026A1 (fr) 1992-11-07 1993-10-29 Toner electrostatique renfermant des cristaux liquides amphiphiles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4237661.0 1992-11-07
DE19924237661 DE4237661A1 (de) 1992-11-07 1992-11-07 Elektrostatische Toner, enthaltend amphiphile Flüssigkristalle

Publications (1)

Publication Number Publication Date
WO1994011789A1 true WO1994011789A1 (fr) 1994-05-26

Family

ID=6472356

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/003020 WO1994011789A1 (fr) 1992-11-07 1993-10-29 Toner electrostatique renfermant des cristaux liquides amphiphiles

Country Status (5)

Country Link
EP (1) EP0671026A1 (fr)
JP (1) JPH08503083A (fr)
CA (1) CA2147171A1 (fr)
DE (1) DE4237661A1 (fr)
WO (1) WO1994011789A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0199211A2 (fr) * 1985-04-17 1986-10-29 BASF Aktiengesellschaft Composés liquides cristallins amphiphiles
EP0233544A2 (fr) * 1986-02-15 1987-08-26 Bayer Ag Toner électrophotographique
US4851561A (en) * 1987-12-17 1989-07-25 Eastman Kodak Company Quaternary ammonium salts
DE4040468A1 (de) * 1989-12-28 1991-07-04 Hoechst Ag Biskationische saeureamid- und -imidderivate als ladungssteuermittel

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0199211A2 (fr) * 1985-04-17 1986-10-29 BASF Aktiengesellschaft Composés liquides cristallins amphiphiles
EP0233544A2 (fr) * 1986-02-15 1987-08-26 Bayer Ag Toner électrophotographique
US4851561A (en) * 1987-12-17 1989-07-25 Eastman Kodak Company Quaternary ammonium salts
DE4040468A1 (de) * 1989-12-28 1991-07-04 Hoechst Ag Biskationische saeureamid- und -imidderivate als ladungssteuermittel

Also Published As

Publication number Publication date
EP0671026A1 (fr) 1995-09-13
DE4237661A1 (de) 1994-05-11
JPH08503083A (ja) 1996-04-02
CA2147171A1 (fr) 1994-05-26

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