EP1512051B1 - Utilisation de composes de type cire dans des toners d'impression - Google Patents

Utilisation de composes de type cire dans des toners d'impression Download PDF

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Publication number
EP1512051B1
EP1512051B1 EP03755126A EP03755126A EP1512051B1 EP 1512051 B1 EP1512051 B1 EP 1512051B1 EP 03755126 A EP03755126 A EP 03755126A EP 03755126 A EP03755126 A EP 03755126A EP 1512051 B1 EP1512051 B1 EP 1512051B1
Authority
EP
European Patent Office
Prior art keywords
toner
wax
photo
compounds
formula
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 - Fee Related
Application number
EP03755126A
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German (de)
English (en)
Other versions
EP1512051A1 (fr
Inventor
Gerd Hohner
Michael Bayer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant GmbH
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Filing date
Publication date
Application filed by Clariant GmbH filed Critical Clariant GmbH
Publication of EP1512051A1 publication Critical patent/EP1512051A1/fr
Application granted granted Critical
Publication of EP1512051B1 publication Critical patent/EP1512051B1/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
    • G03G9/087—Binders for toner particles
    • G03G9/08775—Natural macromolecular compounds or derivatives thereof
    • G03G9/08782—Waxes
    • 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

Definitions

  • the present invention relates to the use of waxy, aromatic Unit containing compounds in photo toners and photo toners, such Contain connections.
  • photo toners used consisting of resins, pigments, charge control agents and waxes as well optionally flow aids exist.
  • Form the powdery photo toners When copying the template to be copied usually first on one Transfer roller from, are transferred from there to the copy paper and subsequently thermally fixed.
  • the waxes contained in the toner as a formulation component favor as Separation and anti-offset means the detachment of the photo toner from the fixing roller, act as a bonding agent in the transfer to the paper and contribute to the Preparation of the toner as a dispersing aid for the homogeneous distribution of Pigments.
  • wax components in photo toners are so far predominantly Hydrocarbon waxes such as polyethylene or polypropylene waxes used. These waxes meet the requirements of modern fast-moving Copy machines do not do justice in all aspects.
  • EP 0 291 872 A1 discloses waxy esters of aromatic alcohols and their Use as lubricant for highly transparent thermoplastic materials described.
  • the invention accordingly provides for the use of waxy compounds of the formula (I) in photo toners, wherein R 1 is the group -CH 2 -O-CO-R 3 or -CH (OH) -CH 2 -O-CO-R 3 , R 2 is an alkyl radical having 1 to 4 C atoms or halogen, R 3 is an unbranched alkyl radical having 16 to 36 carbon atoms and m is 1, 2 or 3 and n is 0 to (6-m).
  • R 1 is preferably the group -CH 2 -O-CO-R 3
  • R 2 is an alkyl radical having 1 to 4 C atoms or halogen
  • R 3 is an unbranched alkyl radical having 16 to 36 carbon atoms and m is 1, 2 or 3 and n is 0 to (6-m).
  • the invention furthermore relates to photo toners containing at least one Pigment component, a resin component and a waxy, aromatic Unit-containing component of the formula (I).
  • wax-like compounds of the formula (I) which can be used according to the invention are formed by reacting aromatic compounds of the formula (II) or of the formula (III) with carboxylic acids of the formula (IV) R 3 -COOH
  • R 1 is the group -CH2-O-CO-R 3 or -CH (OH) -CH 2 -O-CO-R 3
  • R 2 is an alkyl radical having 1 to 4 C atoms or halogen, preferably an alkyl radical having 1 to 2 C atoms or chlorine
  • R 3 is an unbranched alkyl radical having 16 to 36 C atoms, preferably having 26 to 32 C atoms
  • R 4 is the group -CH 2 OH or -CH (OH) -CH 2 -OH, preferably -CH 2 OH
  • R 5 is the group such as m is 1, 2 or 3, preferably 1 or 2, and n 0 to (6-m), preferably 0 to 3.
  • Suitable starting compounds of the formula (II) are, for example Benzyl alcohol, o-, m-, p-tolylcarbinol, chlorobenzyl alcohol, bromobenzyl alcohol, 2,4-dimethylbenzyl alcohol, 3,5-dimethylbenzyl alcohol, 3,4,5-trimethylbenzyl alcohol, p-cumene alcohol, 1,2-phthalyl alcohol, 1,3-bis (hydroxymethyl) benzene, 1,4-bis (hydroxy-methyl) benzene.
  • a suitable starting compound of the formula (III) is, for example, styrene oxide.
  • Suitable carboxylic acids of the formula (IV) are, for example, arachic acid, behenic acid, tetracosanic acid, cerotic acid, montanic acid, melissic acid, in particular technical montanic acid, which is essentially a mixture of C 18 -C 36 -carboxylic acids with a predominant proportion of C 26 -C 32 -carboxylic acids and is obtained by oxidative bleaching of raw montan wax (see, for example, Ullmann's Encyclopedia of Industrial Chemistry, 5th ed. 1996, Vol. A 28, pp. 122-150).
  • photo toners generally contain resins based on Polyesters or styrene-acrylate copolymers.
  • a charge control agent the Support transfer of the toner from the photo-roll to the paper-base, are used e.g. quaternary ammonium salts for a positive charge and For example, aluminum azo complexes for a negative charge of the Toner powder used.
  • the Toner powder small amounts of highly dispersed silicas are added.
  • the toners are already in the thermoplastic Mixture of suitable black or color pigments added.
  • styrene-acrylate resin type CPR 100, manufacturer Fa. Mitsui; Glass transition temperature 60 ° C; MFR / 140 ° C 5 g / 10 min
  • a Black pigment carbon black average particle size of 2 ⁇ m, manufacturer: Fa. Timcal
  • a charge control agent Copy Charge N4S, Manufacturer: Clariant GmbH
  • This mixture has now become one Toner powder of average particle size 12 microns (100% ⁇ 20 microns) comminuted.
  • the Toner powder were now still 0.5 parts by weight of a silica-based Flow agent (type HDK, manufacturer: Wacker) added. 5 g of this now free-flowing Mixture was mixed with 95 g of iron powder and into the reservoir of a Copier filled.
  • Example 1 The procedure was analogous to Example 1. Instead of the one used in Example 1 Benzyl montanate wax was used herein according to the invention Reaction product of technical montanic acid and styrene oxide used (Acid number 18 mg KOH / g, dropping point 76 ° C) used. At the same time the Pigment content reduced by 25%. Otherwise, the procedure was as in Example 1. The prints showed the same color depth as a parallel according to Example 1 tested standard without wax. It follows that through the Wax addition a more effective pigment dispersion is achieved.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Developing Agents For Electrophotography (AREA)

Claims (3)

  1. Utilisation dans les toners de photocopieuses de composés cireux de formule (I)
    Figure 00090001
    dans laquelle R1 est le groupe
    -CH2-O-CO-R3 ou -CH (OH) -CH2-O-CO-R3,
    R2 est un radical alkyle avec 1 à 4 atomes de C ou un halogène,
    R3 est un radical alkyle non ramifié avec 16 à 36 atomes de C, et
    m est égal à 1, 2 ou 3 et n est égal à 0 à (6-m).
  2. Utilisation selon la revendication 1, dans laquelle, dans la formule (I), R1 est le groupe -CH2-O-CO-R3,
    R2 est un radical alkyle avec 1 à 4 atomes de C ou un halogène,
    R3 est un radical alkyle non ramifié avec 16 à 36 atomes de C, et
    m est égal à 1, 2 ou 3 et n est égal à 0 à (6-m).
  3. Toners pour photocopieuses contenant au moins un composant pigmentaire, un composant résineux et un composé cireux de formule (I) selon la revendication 1 ou 2.
EP03755126A 2002-05-29 2003-05-20 Utilisation de composes de type cire dans des toners d'impression Expired - Fee Related EP1512051B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10223785 2002-05-29
DE10223785A DE10223785B4 (de) 2002-05-29 2002-05-29 Verwendung von wachsartigen Verbindungen in Fototonern
PCT/EP2003/005448 WO2003100526A1 (fr) 2002-05-29 2003-05-20 Utilisation de composes de type cire dans des toners d'impression

Publications (2)

Publication Number Publication Date
EP1512051A1 EP1512051A1 (fr) 2005-03-09
EP1512051B1 true EP1512051B1 (fr) 2005-11-30

Family

ID=29557368

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03755126A Expired - Fee Related EP1512051B1 (fr) 2002-05-29 2003-05-20 Utilisation de composes de type cire dans des toners d'impression

Country Status (6)

Country Link
US (1) US7276321B2 (fr)
EP (1) EP1512051B1 (fr)
JP (1) JP4121999B2 (fr)
DE (2) DE10223785B4 (fr)
ES (1) ES2253700T3 (fr)
WO (1) WO2003100526A1 (fr)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3716723A1 (de) * 1987-05-19 1988-12-01 Hoechst Ag Wachsartige verbindungen aromatischer alkohole, ihre herstellung und verwendung
SG49550A1 (en) 1994-05-31 1998-06-15 Canon Kk Toner for developing electrostatic images and image forming method
US5747213A (en) * 1995-05-31 1998-05-05 Canon Kabushiki Kaisha Image forming method and heat fixing method using a toner including a wax
JP3825922B2 (ja) 1997-08-29 2006-09-27 キヤノン株式会社 静電荷像現像用トナー及び画像形成方法
WO2001006321A1 (fr) 1999-07-15 2001-01-25 Fujitsu Limited Poudre imprimante pour electrophotographie et procede de formation d'images
US6492084B2 (en) 2000-05-01 2002-12-10 Ricoh Company, Ltd. Toner for use in electrophotography and image formation method using the toner
US6653039B2 (en) 2001-04-27 2003-11-25 Ricoh Company Limited Toner, and electrophotographic image forming method and apparatus using the toner
EP1280013B1 (fr) 2001-07-23 2008-10-15 Ricoh Company, Ltd. Révélateur sans huile

Also Published As

Publication number Publication date
US7276321B2 (en) 2007-10-02
EP1512051A1 (fr) 2005-03-09
WO2003100526A1 (fr) 2003-12-04
ES2253700T3 (es) 2006-06-01
DE10223785B4 (de) 2006-03-23
DE10223785A1 (de) 2003-12-18
DE50301813D1 (de) 2006-01-05
JP4121999B2 (ja) 2008-07-23
US20050147907A1 (en) 2005-07-07
JP2005534949A (ja) 2005-11-17

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