EP1512051A1 - Use of wax-like compounds in photo toner - Google Patents

Use of wax-like compounds in photo toner

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Publication number
EP1512051A1
EP1512051A1 EP03755126A EP03755126A EP1512051A1 EP 1512051 A1 EP1512051 A1 EP 1512051A1 EP 03755126 A EP03755126 A EP 03755126A EP 03755126 A EP03755126 A EP 03755126A EP 1512051 A1 EP1512051 A1 EP 1512051A1
Authority
EP
European Patent Office
Prior art keywords
toner
formula
compounds
alkyl radical
wax
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.)
Granted
Application number
EP03755126A
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German (de)
French (fr)
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EP1512051B1 (en
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
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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/en
Application granted granted Critical
Publication of EP1512051B1 publication Critical patent/EP1512051B1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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 compounds containing aromatic units in photo toners and photo toners containing such compounds.
  • So-called photo toners are usually used in modern copying processes, which consist of resins, pigments, charge control agents and waxes and, if appropriate, flow aids.
  • the powdery photo toners usually initially image the original to be copied on a transfer roller, are transferred from there to the copy paper and then thermally fixed.
  • the waxes contained in the toner as a recipe component promote the release of the photo toner from the fixing roller as a separating and anti-offset agent, act as an adhesion promoter during the transfer to the paper and contribute to the homogeneous distribution of the pigments during the production of the toner as a dispersion aid.
  • waxes such as polyethylene or polypropylene waxes have been used as wax components in photo toners. These waxes do not meet all the requirements of modern, high-speed copying machines.
  • wax components with an improved anti-offset effect, an improved effect with regard to the adhesion of the print to the paper, and further optimized pigment-dispersing properties.
  • EP 0 291 872 A1 describes waxy esters of aromatic alcohols and their use as lubricants for highly transparent thermoplastic materials.
  • waxes of this type achieve a more homogeneous dispersion of the pigment in the production of the toner and in the fixing process, an improved anti-offset effect and increased adhesion of the print to the paper.
  • the invention accordingly relates to the use of waxy compounds of the formula (I)
  • R 1 is the group
  • R 2 is an alkyl radical with 1 to 4 carbon atoms or halogen
  • R 3 is an unbranched alkyl radical with 16 to 36 C atoms and m is 1, 2 or 3 and n is 0 to (6-m).
  • R 1 is preferably the group -CH 2 -0-CO-R 3
  • R 2 is an alkyl radical having 1 to 4 carbon atoms or halogen
  • R 3 is an unbranched alkyl radical with 16 to 36 C atoms and m 1, 2 or 3 and n 0 to (6-m).
  • the invention further relates to photo toners containing at least one pigment component, a resin component and a waxy component containing the aromatic units of the formula (I).
  • waxy compounds of the formula (I) which can be used according to the invention are formed by reacting aromatic compounds of the formula (II)
  • R 1 the group
  • R 2 is an alkyl radical with 1 to 4 carbon atoms or halogen, preferably one
  • R 3 is an unbranched alkyl radical with 16 to 36 carbon atoms, preferably with 26 to
  • R 4 is the group -CH 2 OH or -CH (OH) -CH 2 -OH, preferably -CH 2 OH,
  • 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-cuminal alcohol, 1 , 2-phthalyl alcohol, 1,3-bis (hydroxymethyl) benzene, 1,4-bis (hydroxymethyl) benzene.
  • a suitable starting compound of the formula (III) is, for example, styrene oxide.
  • Suitable carboxylic acids of the formula (IV) are, for example, arachidic acid,
  • photo toners generally contain resins based on polyesters or styrene-acrylate copolymers.
  • charge control agents which support the transfer of the toner from the photo roller to the paper base, e.g. quaternary ammonium salts for a positive charge and, for example, aluminum azo complexes for a negative charge of the toner powder.
  • quaternary ammonium salts for a positive charge
  • aluminum azo complexes for a negative charge of the toner powder.
  • small amounts of highly disperse silicas can be added to the toner powder.
  • suitable black or color pigments are added to the toners in the thermoplastic mixture.
  • styrene-acrylate resin type CPR 100, manufacturer Mitsui; glass temperature 60 ° C; MFR / 140 ° C 5 g / 10 min
  • a black pigment carbon black of average particle size of 2 ⁇ m; manufacturer: Timcal
  • a charge control agent Copy Charge N4S, manufacturer: Clariant GmbH
  • This mixture was then ground to a toner powder with an average particle size of 12 ⁇ m (100% ⁇ 20 ⁇ m).
  • a silica-based flow agent (type HDK, manufacturer: Wacker) was then added to the toner powder. 5 g of this now free-flowing mixture were mixed with 95 g of iron powder and filled into the reservoir of a copier.
  • Example 1 The procedure was analogous to Example 1. Instead of the benzyl montanate wax used in Example 1, a reaction product of technical montanic acid and styrene oxide which can be used according to the invention was used here (acid number 18 mg KOH / g, dropping point 76 ° C.). At the same time, the pigment content was reduced by 25%. Otherwise, the procedure was as in Example 1. The prints showed the same color depth as a standard tested in parallel according to Example 1 without wax. This shows that more effective pigment dispersion is achieved through the addition of wax.

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

Abstract

The invention relates to the use of wax-like compounds of formula (I) in photo toner. In formula (I), R1 represents the group -CH2-O-CO-R3 or -CH(OH)-CH2-O-CO-R3, R2 represents an alkyl radical comprising between 1 and 4 C atoms or halogen, R3 represents an unbranched alkyl radical comprising between 16 and 36 C atoms, m is 1, 2 or 3, and n is between 0 and (6-m). The invention also relates to corresponding photo toner.

Description

Beschreibung description
Verwendung von wachsartigen Verbindungen in FototonernUse of waxy compounds in photo toners
Die vorliegende Erfindung betrifft die Verwendung von wachsartigen, aromatische Einheiten enthaltenden Verbindungen in Fototonern sowie Fototoner, die derartige Verbindungen enthalten.The present invention relates to the use of waxy compounds containing aromatic units in photo toners and photo toners containing such compounds.
Üblicherweise werden in modernen Kopierverfahren sogenannte Fototoner eingesetzt, die aus Harzen, Pigmenten, Ladungssteuermitteln und Wachsen sowie gegebenenfalls Fliesshilfsmittel bestehen. Die pulverförmigen Fototoner bilden beim Kopiervorgang die zu kopierende Vorlage üblicherweise zunächst auf einer Übertragungswalze ab, werden von dort auf das Kopierpapier transferiert und anschließend thermisch fixiert.So-called photo toners are usually used in modern copying processes, which consist of resins, pigments, charge control agents and waxes and, if appropriate, flow aids. During the copying process, the powdery photo toners usually initially image the original to be copied on a transfer roller, are transferred from there to the copy paper and then thermally fixed.
Die im Toner als Rezepturkomponente enthaltenen Wachse begünstigen als Trenn- und anti-offset-Mittel die Ablösung des Fototoners von der Fixierwalze, wirken als Haftvermittler bei der Übertragung auf das Papier und tragen bei der Herstellung des Toners als Dispergierhilfe zur homogenen Verteilung der Pigmente bei.The waxes contained in the toner as a recipe component promote the release of the photo toner from the fixing roller as a separating and anti-offset agent, act as an adhesion promoter during the transfer to the paper and contribute to the homogeneous distribution of the pigments during the production of the toner as a dispersion aid.
Der Bedarf nach immer schneller arbeitenden Kopierern verlangt entsprechend flink ansprechende Tonersysteme und stellt hohe Anforderungen an die Einzelkomponenten der Tonerrezeptur.The need for copiers that work ever faster demands correspondingly responsive toner systems and places high demands on the individual components of the toner formulation.
Als Wachskomponenten in Fototonern werden bisher überwiegend Kohlenwasserstoff-Wachse wie Polyethylen- oder Polypropylenwachse eingesetzt. Diese Wachse werden den Anforderungen, die moderne schnell laufende Kopiermaschinen stellen, nicht in allen Aspekten gerecht. Insbesondere besteht Bedarf nach Wachskomponenten mit verbesserter anti-offset-Wirkung, verbesserter Wirkung bezüglich der Haftung des Drucks auf dem Papier sowie weiter optimierten pigmentdispergierenden Eigenschaften. In EP 0 291 872 A1 werden wachsartige Ester aromatischer Alkohole und ihre Verwendung als Gleitmittel für hochtransparente thermoplastische Kunststoffe beschrieben.So far, mainly hydrocarbon waxes such as polyethylene or polypropylene waxes have been used as wax components in photo toners. These waxes do not meet all the requirements of modern, high-speed copying machines. In particular, there is a need for wax components with an improved anti-offset effect, an improved effect with regard to the adhesion of the print to the paper, and further optimized pigment-dispersing properties. EP 0 291 872 A1 describes waxy esters of aromatic alcohols and their use as lubricants for highly transparent thermoplastic materials.
Überraschenderweise wurde nun gefunden, dass sich derartige polare, aromatische Gruppen enthaltenden wachsartigen Verbindungen in besonders vorteilhafter Weise als Additive für Fototoner eignen. Insbesondere wird mit derartigen Wachsen eine homogenere Dispergierung des Pigments bei der Herstellung des Toners sowie beim Fixiervorgang eine verbesserte anti-offset- Wirkung und eine erhöhte Haftung des Drucks auf dem Papier erreicht.Surprisingly, it has now been found that such polar, aromatic groups-containing wax-like compounds are particularly advantageously suitable as additives for photo toners. In particular, waxes of this type achieve a more homogeneous dispersion of the pigment in the production of the toner and in the fixing process, an improved anti-offset effect and increased adhesion of the print to the paper.
Gegenstand der Erfindung ist demnach die Verwendung von wachsartigen Verbindungen der Formel (I)The invention accordingly relates to the use of waxy compounds of the formula (I)
in Fototonern, in photo toners,
worin R1 die Gruppewherein R 1 is the group
-CH2-O-CO-R3 oder -CH(OH)-CH2-0-CO-R3, R2 ein Alkylrest mit 1 bis 4 C-Atomen oder Halogen, R3 ein unverzweigter Alkylrest mit 16 bis 36 C-Atomen sowie m 1 , 2 oder 3 und n 0 bis (6-m) ist.-CH 2 -O-CO-R 3 or -CH (OH) -CH 2 -0-CO-R 3 , R 2 is an alkyl radical with 1 to 4 carbon atoms or halogen, R 3 is an unbranched alkyl radical with 16 to 36 C atoms and m is 1, 2 or 3 and n is 0 to (6-m).
Bevorzugt ist in Formel (I) R1 die Gruppe -CH2-0-CO-R3, R2 ein Alkylrest mit 1 bis 4 C-Atomen oder Halogen,In formula (I) R 1 is preferably the group -CH 2 -0-CO-R 3 , R 2 is an alkyl radical having 1 to 4 carbon atoms or halogen,
R3 ein unverzweigter Alkylrest mit 16 bis 36 C-Atomen sowie m 1 , 2 oder 3 und n 0 bis (6-m). Gegenstand der Erfindung sind ferner Fototoner, enthaltend mindestens eine Pigmentkomponente, eine Harzkomponente und eine wachsartige, aromatische Einheiten enthaltende Komponente der Formel (I).R 3 is an unbranched alkyl radical with 16 to 36 C atoms and m 1, 2 or 3 and n 0 to (6-m). The invention further relates to photo toners containing at least one pigment component, a resin component and a waxy component containing the aromatic units of the formula (I).
Die erfindungsgemäß verwendbaren wachsartigen Verbindungen der Formel (I) entstehen durch Umsetzung von aromatischen Verbindungen der Formel (II)The waxy compounds of the formula (I) which can be used according to the invention are formed by reacting aromatic compounds of the formula (II)
oder der Formel (III) or of the formula (III)
mit Carbonsäuren der Formel (IV)with carboxylic acids of formula (IV)
R3-COOH (IV).R 3 -COOH (IV).
In diesen Formeln bedeutenMean in these formulas
R1 die GruppeR 1 the group
-CH2-0-CO-R3 oder -CH(0H)-CH2-O-CO-R3,-CH2-0-CO-R 3 or -CH (0H) -CH 2 -O-CO-R 3 ,
R2 einen Alkylrest mit 1 bis 4 C-Atomen oder Halogen, vorzugsweise einenR 2 is an alkyl radical with 1 to 4 carbon atoms or halogen, preferably one
Alkylrest mit 1 bis 2 C-Atomen oder Chlor,Alkyl radical with 1 to 2 carbon atoms or chlorine,
R3 einen unverzweigten Alkylrest mit 16 bis 36 C-Atomen, vorzugsweise mit 26 bisR 3 is an unbranched alkyl radical with 16 to 36 carbon atoms, preferably with 26 to
32 C-Atomen,32 carbon atoms,
R4 die Gruppe -CH2OH oder -CH(OH)-CH2-OH, vorzugsweise -CH2OH,R 4 is the group -CH 2 OH or -CH (OH) -CH 2 -OH, preferably -CH 2 OH,
R5die GruppeR 5 the group
-CH-CH,-CH-CH,
\ /\ /
O sowie m 1 , 2 oder 3, vorzugsweise 1 oder 2, und n 0 bis (6-m), vorzugsweise 0 bis 3.O and m 1, 2 or 3, preferably 1 or 2, and n 0 to (6-m), preferably 0 to 3.
Geeignete Ausgangsverbindungen der Formel (II) sind beispielsweise Benzylalkohol, o-, m-, p-Tolylcarbinol, Chlorbenzylalkohol, Brombenzylalkohol, 2,4-Dimethylbenzylalkohol, 3,5-Dimethylbenzylalkohol, 3,4,5- Trimethylbenzylalkohol, p-CuminalkohoI, 1 ,2-Phtalylalkohol, 1 ,3- Bis(hydroximethyl)benzol, 1 ,4-Bis(hydroxy-methyl)benzol.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-cuminal alcohol, 1 , 2-phthalyl alcohol, 1,3-bis (hydroxymethyl) benzene, 1,4-bis (hydroxymethyl) benzene.
Eine geeignete Ausgangsverbindung der Formel (III) ist beispielsweise Styroloxid.A suitable starting compound of the formula (III) is, for example, styrene oxide.
Geeignete Carbonsäuren der Formel (IV) sind beispielsweise Arachinsäure,Suitable carboxylic acids of the formula (IV) are, for example, arachidic acid,
Behensäure, Tetracosansäure, Cerotinsäure, Montansäure, Melissinsäure, insbesondere technische Montansäure, welche im wesentlichen ein Gemisch ausBehenic acid, tetracosanoic acid, cerotic acid, montanic acid, melissic acid, in particular technical montanic acid, which essentially consists of a mixture
Ci8-C36-Carbonsäuren mit einem überwiegenden Anteil an C26-C32-Carbonsäuren ist und durch oxidative Bleichung von Rohmontanwachs gewonnen wird (vgl. z.B.Ci 8 -C 36 carboxylic acids with a predominant proportion of C2 6 -C 32 carboxylic acids and is obtained by oxidative bleaching of crude montan wax (cf. e.g.
Ullmann's Encyclopedia of Industrial Chemistry, 5. Aufl. 1996, Vol. A 28,Ullmann's Encyclopedia of Industrial Chemistry, 5th ed. 1996, Vol. A 28,
S. 122 - 150).Pp. 122 - 150).
Verfahren zur Herstellung der erfindungsgemäß verwendbaren Verbindungen sind in EP-0 291 872 A1 angegeben.Processes for the preparation of the compounds which can be used according to the invention are specified in EP-0 291 872 A1.
Fototoner enthalten als Basiskomponente in der Regel Harze auf Basis von Polyestern oder Styrol-Acrylat-Copolymeren. Als Ladungssteuermittel , die die Übertragung des Toners von der Fotowalze auf die Papierunterlage unterstützen, werden z.B. quaternäre Ammoniumsalze für eine positive Ladung und beispielsweise Aluminium-Azo-Complexe für eine negative Aufladung des Tonerpulvers verwendet. Zur Unterstützung der Rieselfähigkeit können dem Tonerpulver geringe Mengen hochdisperser Kieselsäuren zugegeben werden.As a basic component, photo toners generally contain resins based on polyesters or styrene-acrylate copolymers. As charge control agents which support the transfer of the toner from the photo roller to the paper base, e.g. quaternary ammonium salts for a positive charge and, for example, aluminum azo complexes for a negative charge of the toner powder. To support the free-flowing properties, small amounts of highly disperse silicas can be added to the toner powder.
Je nach gewünschter Farbe werden den Tonern bereits in der thermoplastischen Mischung geeignete Schwarz- oder Farbpigmente zugegeben. BeispieleDepending on the desired color, suitable black or color pigments are added to the toners in the thermoplastic mixture. Examples
Die im folgenden angeführten Säurezahlen wurden nach DIN 53402, die Tropfpunkte nach DIN 51801/2 bestimmt.The acid numbers listed below were determined according to DIN 53402, the dropping points according to DIN 51801/2.
Beispiel 1 :Example 1 :
90 Gew.-Teile eines Styrol-Acrylat Harzes (Typ CPR 100, Hersteller Fa. Mitsui; Glastemperatur 60°C; MFR/140°C 5 g/10 min) wurden mit 4 Gew.-Teilen eines Schwarzpigments (Russ mittlerer Teilchengrösse von 2 μm; Hersteller: Fa. Timcal), 1 ,0 Gew.-Teile eines Ladungssteuermittels (Copy Charge N4S, Hersteller: Clariant GmbH) und 4 Gew.-Teilen eines erfindungsgemäss eingesetzten Umsetzungsprodukts aus technischer Montansäure und Benzylalkohol mit einer Säurezahl von 25 und einem Tropfpunkt von 77°C bei 150°C in einem Kneter homogen vermischt. Diese Mischung wurde nun zu einem Tonerpulver der mittleren Teilchengrösse 12 μm (100 % < 20 μm) zerkleinert. Dem Tonerpulver wurden nun noch 0,5 Gew.-Teile eines Silika-basierten Fliessmittels(Typ HDK, Hersteller: Wacker) zugesetzt. 5 g dieser nun rieselfähigen Mischung wurden mit 95 g Eisenpulver vermischt und in den Vorratsbehälter eines Kopierers gefüllt.90 parts by weight of a styrene-acrylate resin (type CPR 100, manufacturer Mitsui; glass temperature 60 ° C; MFR / 140 ° C 5 g / 10 min) were mixed with 4 parts by weight of a black pigment (carbon black of average particle size of 2 μm; manufacturer: Timcal), 1.0 part by weight of a charge control agent (Copy Charge N4S, manufacturer: Clariant GmbH) and 4 parts by weight of a reaction product of technical montanic acid and benzyl alcohol with an acid number of 25 and a dropping point of 77 ° C at 150 ° C mixed homogeneously in a kneader. This mixture was then ground to a toner powder with an average particle size of 12 μm (100% <20 μm). 0.5 part by weight of a silica-based flow agent (type HDK, manufacturer: Wacker) was then added to the toner powder. 5 g of this now free-flowing mixture were mixed with 95 g of iron powder and filled into the reservoir of a copier.
Mit Hilfe der im Kopierer befindlichen photomagnetischen Walze wurde in einer Fläche von 20x100 mm Tonerpulver auf ein Papier aufgebracht. Dieses Bild wurde dann mit einer Walzenanordnung, bestehend aus einer starren heizbaren Walze und einer elastischen kalten Walze, bei 160°C und einer Durchlaufgeschwindigkeit von 150 mm/s fixiert. Anschließend wurde ein weiteres weises Blatt durch die heiße Walzenpaarung geführt und auf Tonerrückstände untersucht. Am weißen Blatt waren keine "ghost pictures" zu erkennen.With the help of the photomagnetic roller in the copier, toner powder was applied to a paper in an area of 20 × 100 mm. This image was then fixed with a roller arrangement consisting of a rigid heatable roller and an elastic cold roller at 160 ° C. and a throughput speed of 150 mm / s. Another white sheet was then passed through the hot roller pair and examined for toner residues. No "ghost pictures" could be recognized on the white sheet.
Beispiel 2:Example 2:
1 g des Tonerpulvers aus Beispiel 1 wurden mit 2 g Ethanol verrührt und mit einem Rakel auf eine Papierunterlage aufgetragen (Schichtdicke: 40 μm). Nach Abtrocknung des Lösemittels bei 40°C wurde die übrige Pulverschicht bei 140°C und 120 mm/s Durchlaufgeschwindigkeit fixiert. Die fixierte Tonerschicht wurde mit einem Prüfbau-Abriebtest, wie er bei der Prüfung von Druckfarben verwendet wird, untersucht. Die Reibung Papier auf Toner mit 50 Reibbewegungen zeigte dabei keinen meßbaren Abrieb. Nach Faltung der Tonerschicht um 180° wurden keine sichtbaren Faltlinien und Abplatzer festgestellt.1 g of the toner powder from Example 1 was stirred with 2 g of ethanol and applied to a paper base using a doctor blade (layer thickness: 40 μm). To Drying the solvent at 40 ° C, the remaining powder layer was fixed at 140 ° C and 120 mm / s throughput. The fixed toner layer was examined using a test construction abrasion test as used in the testing of printing inks. The rubbing of paper on toner with 50 rubbing movements showed no measurable abrasion. After folding the toner layer by 180 °, no visible fold lines and flaking were found.
Beispiel 3:Example 3:
Es wurde analog Beispiel 1 verfahren. Anstelle des in Beispiel 1 eingesetzten Benzylmontanat-Wachses wurde hier ein erfindungsgemäss verwendbares Umsetzungsprodukt aus technischer Montansäure und Styroloxid eingesetzt (Säurezahl 18 mg KOH/g, Tropfpunkt 76°C) eingesetzt. Gleichzeitig wurde der Pigmentanteil um 25 % reduziert. Ansonsten wurde wie in Beispiel 1 verfahren. Die Drucke zeigten die gleiche Farbtiefe wie ein parallel gemäß Beispiel 1 geprüfter Standard ohne Wachs. Daraus geht hervor, dass durch den Wachszusatz eine wirksamere Pigmentdispergierung erreicht wird. The procedure was analogous to Example 1. Instead of the benzyl montanate wax used in Example 1, a reaction product of technical montanic acid and styrene oxide which can be used according to the invention was used here (acid number 18 mg KOH / g, dropping point 76 ° C.). At the same time, the pigment content was reduced by 25%. Otherwise, the procedure was as in Example 1. The prints showed the same color depth as a standard tested in parallel according to Example 1 without wax. This shows that more effective pigment dispersion is achieved through the addition of wax.

Claims

Patentansprüche claims
1. Verwendung von wachsartigen Verbindungen der Formel (I) in Fototonern,1. Use of waxy compounds of the formula (I) in photo toners,
worin R1 die Gruppewherein R 1 is the group
-CH2-O-CO-R3 oder -CH(OH)-CH2-O-CO-R3, R2 ein Alkylrest mit 1 bis 4 C-Atomen oder Halogen, R3 ein unverzweigter Alkylrest mit 16 bis 36 C-Atomen sowie m 1 , 2 oder 3 und n 0 bis (6-m) ist.-CH 2 -O-CO-R 3 or -CH (OH) -CH 2 -O-CO-R 3 , R 2 is an alkyl radical with 1 to 4 carbon atoms or halogen, R 3 is an unbranched alkyl radical with 16 to 36 C atoms and m is 1, 2 or 3 and n is 0 to (6-m).
2. Verwendung gemäß Anspruch 1 , worin in Formel (I) R1 die Gruppe -CH2-O-CO-R3, R2 ein Alkylrest mit 1 bis 4 C-Atomen oder Halogen,2. Use according to claim 1, wherein in formula (I) R 1 is the group -CH 2 -O-CO-R 3 , R 2 is an alkyl radical having 1 to 4 carbon atoms or halogen,
R3 ein unverzweigter Alkylrest mit 16 bis 36 C-Atomen sowie m 1 , 2 oder 3 und n 0 bis (6-m) ist.R 3 is an unbranched alkyl radical having 16 to 36 carbon atoms and m 1, 2 or 3 and n is 0 to (6-m).
3. Fototoner, enthaltend mindestens eine Pigmentkomponente, eine Harzkomponente und eine wachsartige Verbindung der Formel (I) gemäß den Ansprüchen 1 oder 2. 3. Photo toner containing at least one pigment component, a resin component and a waxy compound of the formula (I) according to claims 1 or 2.
EP03755126A 2002-05-29 2003-05-20 Use of wax-like compounds in photo toner Expired - Fee Related EP1512051B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10223785 2002-05-29
DE10223785A DE10223785B4 (en) 2002-05-29 2002-05-29 Use of waxy compounds in photo-toners
PCT/EP2003/005448 WO2003100526A1 (en) 2002-05-29 2003-05-20 Use of wax-like compounds in photo toner

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EP1512051A1 true EP1512051A1 (en) 2005-03-09
EP1512051B1 EP1512051B1 (en) 2005-11-30

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

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* Cited by examiner, † Cited by third party
Title
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US7276321B2 (en) 2007-10-02
WO2003100526A1 (en) 2003-12-04
ES2253700T3 (en) 2006-06-01
DE10223785B4 (en) 2006-03-23
DE10223785A1 (en) 2003-12-18
DE50301813D1 (en) 2006-01-05
JP4121999B2 (en) 2008-07-23
US20050147907A1 (en) 2005-07-07
EP1512051B1 (en) 2005-11-30
JP2005534949A (en) 2005-11-17

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