EP0895131A2 - Verwendung von Inter-Polyelektrolyt-Komplexen als Ladungssteuermittel - Google Patents
Verwendung von Inter-Polyelektrolyt-Komplexen als Ladungssteuermittel Download PDFInfo
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- EP0895131A2 EP0895131A2 EP98113654A EP98113654A EP0895131A2 EP 0895131 A2 EP0895131 A2 EP 0895131A2 EP 98113654 A EP98113654 A EP 98113654A EP 98113654 A EP98113654 A EP 98113654A EP 0895131 A2 EP0895131 A2 EP 0895131A2
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- acid
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
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- 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
- G03G9/08791—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by the presence of specified groups or side chains
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- 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
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- 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
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- 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
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- 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
- Y10S977/00—Nanotechnology
- Y10S977/70—Nanostructure
- Y10S977/773—Nanoparticle, i.e. structure having three dimensions of 100 nm or less
- Y10S977/775—Nanosized powder or flake, e.g. nanosized catalyst
- Y10S977/776—Ceramic powder or flake
Definitions
- the present invention is in the technical field of charge control agents in toners and developers for electrophotographic recording processes, in Powders and powder coatings for surface coating, in electret materials, especially in electret fibers, as well as in separation processes.
- a photoconductor is used "latent charge image” generated.
- This "latent charge pattern” is created by application developed an electrostatically charged toner, which then, for example, on Transfer paper, textiles, foils or plastic and for example by means of Pressure, radiation, heat or exposure to solvents.
- Typical toners are one or two component powder toners (also one or Two-component developer), there are also special toners, such as e.g. B. magnetic toner, liquid toner or polymerization toner in use.
- Under Polymerization toners are to be understood as those toners which, for. B. by Suspension polymerization (condensation) or emulsion polymerization arise and lead to improved particle properties of the toner.
- such toners are also meant, which are basically in non-aqueous Dispersions are generated.
- a measure of the toner quality is its specific charge q / m (charge per Unit of mass). In addition to the sign and the amount of the electrostatic charge all the fast reaching of the desired load height and consistency this charge over a longer activation period is crucial Quality criterion. In addition, the toner is insensitive to climate influences, such as temperature and humidity, are another important factor Eligibility criterion.
- Both positively and negatively chargeable toners are used in copiers and laser printers depending on the type of process and device.
- To electrophotographic toners or developers with either positive or To maintain negative charge charge control agents are often added.
- Toner binders usually have a strong dependency on the charge Having activation time, it is the task of a charge control agent, on the one hand Set the sign and amount of the toner charge and secondly the To counteract the drift of the toner binder and for the constancy of the To ensure toner charging.
- Charge control agents that cannot prevent the toner or developer from prolonged use shows a high charge drift (aging) that even can cause the toner or developer to undergo charge reversal therefore unsuitable for practice.
- black, blue or dark charge control agents can be used for color toners because of the coloristic Charge control agent without own color required.
- the three toners yellow, cyan and magenta must be next to the precisely defined color requirements also with regard to their triboelectric Properties must be precisely matched to each other, since they are in the same one after the other Device.
- Colorants are known to be the triboelectric charge of toners can partially influence sustainably. Because of the different triboelectric effects of colorants and the resulting partial very pronounced influence on the toner chargeability, it is not possible Almost add colorants to a toner base formulation once created. Rather, it may be necessary to have a separate formulation for each colorant create the type and quantity of the cargo control agent required be tailored.
- the charge control means a have sufficient thermal stability and good dispersibility.
- Typical Incorporation temperatures for charge control agents into the toner resins are included Use of kneaders or extruders between 100 ° C and 200 ° C. Accordingly, a thermal stability of 200 ° C is of great advantage. Important is also that the thermal stability over a longer period (approx. 30 minutes) and is guaranteed in various binder systems. This is significant because recurring matrix effects for early decomposition of the Charge control agent in the toner resin, causing a dark yellow or dark brown coloring of the toner resin takes place and the charge control effect entirely or partially lost.
- Typical toner binders are polymerization, Polyaddition and polycondensation resins such as styrene, styrene acrylate, Styrene butadiene, acrylate, polyester, phenol epoxy resins, and Cycloolefin copolymers, individually or in combination, which contain further ingredients, e.g. B. colorants such as dyes and pigments, waxes or flow aids, can contain or get added afterwards, like finely divided silicas.
- charge control agents can also be used to improve the electrostatic charging of powders and lacquers, in particular in triboelectrically or electrokinetically sprayed powder lacquers, such as those used for the surface coating of objects made of, for example, metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber are used.
- Powder coating technology is used, for example, when painting objects such as garden furniture, camping articles, household appliances, vehicle parts, refrigerators and shelves, as well as when painting complicated-shaped workpieces.
- the powder coating or powder is generally electrostatically charged by one of the following two methods: In the corona process, the powder coating or the powder is guided past a charged corona and thereby charged, in the triboelectric or electrokinetic process the principle of frictional electricity is used.
- the powder coating or powder is electrostatically sprayed Charge that is the charge of the friction partner, generally a hose or Spray tube, for example made of polytetrafluoroethylene, is opposite.
- powder coating resins are typically epoxy resins containing carboxyl and hydroxyl groups Polyester resins, polyurethane and acrylic resins together with the usual hardeners used. Combinations of resins are also used. So be for example, often epoxy resins in combination with carboxyl and hydroxyl-containing polyester resins used.
- Typical hardener components for epoxy resins are, for example, acid anhydrides, Imidazoles and dicyandiamide and their derivatives.
- Polyester resins are typical hardener components, for example acid anhydrides, masked isocyanates, bisacyl urethanes, phenolic resins and melamine resins.
- polyester resins containing carboxyl groups are typical hardener components for example triglycidyl isocyanurates or epoxy resins.
- acrylic resins as typical hardener components, for example oxazolines, isocyanates, Triglycidyl isocyanurates or dicarboxylic acids are used.
- the disadvantage of insufficient charging is especially with triboelectric or electrokinetically sprayed powders and powder coatings based on Polyester resins, especially carboxyl-containing polyesters, or on the Basis of so-called mixed powders, also called hybrid powders have been watching.
- Mixed powders are powder coatings whose Resin base made from a combination of epoxy resin and carboxyl-containing Polyester resin is made.
- the mixed powders form the basis for the in practice most commonly represented powder coatings.
- Insufficient charging of the above Powder and powder coatings leads to a separation rate and wrap around coating workpiece are insufficient.
- the term "wrap around” is a measure to what extent there is a powder or powder coating on the workpiece to be coated also on the back, cavities, gaps and especially on the inner edges and -cuts corners.
- charge control agents are the charge as well the charge stability behavior of electret materials, in particular Electret fibers can significantly improve (DE-A-43 21 289).
- Electret fibers So far mainly in connection with the problem of fine dust filtration have been described.
- the filter materials described differ both regarding the materials from which the fibers are made as well as regarding the How the electrostatic charge is applied to the fibers.
- Typical electret materials are based on polyolefins, halogenated polyolefins, Polyacrylates, polyacrylonitriles, polystyrenes or fluoropolymers, such as for example polyethylene, polypropylene, polytetrafluoroethylene and perfluorinated Ethylene and propylene, or on polyesters, polycarbonates, polyamides, Polyimides, polyether ketones, on polyarylene sulfides, in particular Polyphenylene sulfides, on polyacetals, cellulose esters, polyalkylene terephthalates as well as mixtures thereof.
- Electret materials, especially electret fibers can for example for (ultra-fine) dust filtration.
- the electret materials can get their charge in different ways, namely by corona or Tribo charging.
- charge control agents in electrostatic Separation processes can be.
- Y. Higashiyama et al. J. Electrostatics 30, pp 203 - 212 (1993)
- Charge control agent of trimethyl-phenyl-ammonium-tetraphenylborate, such as polymers can be separated from each other for recycling purposes.
- Charge control agents load "Low Density Polyethylene (LDPE)” and "High Density Polyethylene "(HDPE) is largely similar to frictional electrical Charge control agent addition charge LDPE strongly positive and HDPE strongly negative and can be separated so well.
- LDPE Low Density Polyethylene
- HDPE High Density Polyethylene
- Polymers can be thought of, for example, a polymer within the shift triboelectric voltage series and a corresponding Maintain separation effect.
- Other polymers can also be used in this way such as B. polypropylene (PP) and / or polyethylene terephthalate (PET) and / or Separate polyvinyl chloride (PVC).
- PP polypropylene
- PET polyethylene terephthalate
- PVC Separate polyvinyl chloride
- charge control agents are used as "electroconductivity providing agents” (ECPA) (JP 05 163 449-A) used in inks for inkjet printers.
- Charge control agents are well known in the literature. However, the previously known charge control agents have a number of disadvantages that the Restrict use in practice or make it impossible, e.g. B. Own color, photo or thermolability, low stability in the toner binder, insufficient effectiveness with regard to the desired sign of the cargo (positive or negative charge), charge height or charge constancy, Dispersibility.
- the object of the present invention was therefore to improve, especially to find effective colorless charge control agents.
- the connections are said to have high thermal stability exhibit.
- they should be in various practical toner binders such as polyesters, polystyrene acrylates or polystyrene butadienes / epoxy resins and Cycloolefin copolymers are good and dispersible without decomposition.
- they should they be ecologically / toxicologically safe, d. H. be non-toxic and free of heavy metals.
- their effect should be largely independent of the resin / carrier combination to open up a wide application.
- they should be in common powder coating binders and electret materials such.
- B. polyester (PES), Epoxy, PES-epoxy hybrid, polyurethane, acrylic systems and polypropylenes are good and be dispersible without decomposition and do not cause discoloration of the resins.
- IPEC inter-polyelectrolyte complexes
- these compounds are preferably without their own color and can be easily mixed in disperse conventional toner, powder coating and electret binders.
- IPEC IPEC
- anionic Macromolecule polyanion
- cationic macromolecule polycation
- the former consist of one from 0.9: 1.1 to 1.1: 0.9, for example approximately 1: 1 molar ratio of cationic to anionic groups in the sense of polymer salt formation, while only some of the ionic ones in the non-stoichiometric polyelectrolyte complexes Groups of a polyelectrolyte component by oppositely charged Groups of the second component is saturated, the rest is through low molecular weight ions, for example metal cations or inorganic anions, neutralized.
- the non-stoichiometric IPEC arise when the deficit is too low submitted solution of a polymer component (host polyelectrolyte) added second component (guest polyelectrolyte), d. H.
- IPEC IPEC are water soluble especially if the added second component compared to the presented first has a significantly lower degree of polymerization and thus a such macromolecule of the second component only part of the polymer chain saturate other component in terms of charge.
- IPEC are used e.g. B. as a protein carrier, synthetic viruses, for cleaning or for the separation of proteins, as membrane materials, for influencing Enzyme activities by means of complexation as well as for encapsulation of active substances complex coacervation.
- the present invention relates to the use of inter-polyelectrolyte complexes as a charge control agent and charge enhancer in electrophotographic toners and developers, in triboelectric or electrokinetically sprayable powders and powder coatings and in electret materials.
- both stoichiometric and non-stoichiometric polyelectrolyte complexes are used.
- the non-stoichiometric Complexes it is advantageous if the excess of longer-chain host polyelectrolytes is at least 20%, based on the Total number of IPEC loads.
- IPEC used according to the invention can be produced in accordance with the Information can be made in the literature mentioned above.
- IPEC can be diluted, e.g. B. 0.01 to 1 molar, aqueous solutions of a polybase and a polyacid, or by Combining dilute aqueous solutions of the salts of a polyacid and Polybase with its low molecular counterions or the free polybase, or by addition of an ionic monomer as a low molecular counterion an oppositely charged macro ion and subsequent radical one Polymerization of the monomer (matrix polymerization) can be produced. It is advantageous if the polyanionic and polycationic component in aqueous Medium can be dissolved or suspended.
- the IPEC is isolated for example by precipitation from an aqueous medium, spray drying or Evaporation, preferably by precipitation.
- IPEC used according to the invention can essentially consist of synthetic and / or natural polyanions and synthetic and / or natural polycations.
- the polyanions or polycations can also be derivatives of natural products.
- polyanion-forming compounds are poly (styrene sulfonic acid), poly (acrylic acid), poly (methacrylic acid), poly (maleic acid), poly (itaconic acid), poly (vinyl sulfate), poly (vinyl sulfonic acid), poly (vinyl phosphate), poly ( acrylic acid-co-maleic acid), poly (styrene sulfonic acid-co-maleic acid), poly (ethylene-co-acrylic acid), poly (phosphoric acid), poly (silicic acid), hectorite, bentonite, alginic acid, pectic acid, kappa, lambda, iota -Carrageenans, xanthan, gum arabic, dextran sulfate, carboxymethyl dextran, carboxymethyl cellulose, cellulose sulfate, cellulose xanthate, starch sulfate and phosphate, lignosulfonates, gum karaya; Polygalactu
- These derivatives can also contain nonionic functional groups in various degrees of substitution, such as. B. methyl, ethyl, propyl, isopropyl, 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxybutyl groups and esters with aliphatic carboxylic acids (C 2 to C 18 ).
- chitosan which is usually produced by treating chitin with concentrated sodium hydroxide solution with cleavage of the N-acetyl bond. Chitosan with free amino groups is not soluble in water. Salt formation with acids gives chitosonium salts, which are water-soluble cationic polyelectrolytes.
- IPEC used according to the invention can be tailored to the respective Resin / toner system can be matched.
- Compounds used are colorless and free-flowing and high and special constant charge control properties, good thermal stability and good Have dispersibility.
- Another technical advantage of these connections lies in the fact that they are inert towards the different binder systems behave and can therefore be used in a variety of ways.
- Dispersion means the distribution of one substance in another, in the sense of Invention the distribution of a charge control agent in the toner binder, Powder coating binder or electret material.
- the charge control agent particles that after the Dispersion in the binder should be less than 1 micron, preferably less than 0.5 ⁇ m, with a narrow particle size distribution is advantageous.
- the particle size defined by the d 50 value
- coarse particles ⁇ 1 mm
- the particle size and shape is determined either by synthesis and / or Post-treatment adjusted and modified. Often the required property only possible through targeted post-treatment such as grinding and / or drying. Various grinding techniques are available for this. For example, are advantageous Air jet mills, cutting mills, hammer mills, bead mills and impact mills.
- Binder systems around hydrophobic materials Binder systems around hydrophobic materials.
- High water content of the Charge control agents can either prevent wetting or else favor dispersion (flushing). Hence the practicable moisture content substance-specific.
- the compounds of the invention are chemical / physical by the following Characteristics marked:
- the water content determined by the Karl Fischer method, is between 0.1% and 30%, preferably between 1 and 25% and particularly preferably between 1 and 20%, and the water can be adsorbed and / or bound, and so on Percentage can be adjusted by exposure to temperature up to 200 ° C and vacuum to 10 -8 Torr or by adding water.
- the particle size determined by means of light microscopic evaluation or laser light diffraction and defined by the d 50 value, is between 0.01 ⁇ m and 1000 ⁇ m, preferably between 0.1 and 500 ⁇ m and very particularly preferably between 0.5 and 400 ⁇ m.
- IPEC used according to the invention are particularly suitable as colorless, easily dispersible charge control agents for colored toners in combination with colorants.
- inorganic pigments, organic dyes, organic colored pigments, but also white colorants, such as TiO 2 or BaSO 4 , pearlescent pigments and black pigments based on carbon black or iron oxides, are suitable as colorants.
- the compounds used according to the invention are used individually or in combination with one another in a concentration of 0.01 to 50% by weight, preferably 0.5 to 20% by weight, particularly preferably 0.1 to 5.0% by weight , based on the total mixture, incorporated in the binder of the respective toner, developer, lacquer, powder coating, electret material or the electrostatically separable polymer, for example by extrusion or kneading.
- the compounds used according to the invention can be used as dried and ground powders, dispersions or solutions, press cakes, masterbatches, preparations, pastes, as suitable carriers, such as.
- silica gel TiO 2 , Al 2 O 3 , compounds drawn up from aqueous or non-aqueous solution or in any other form are added.
- the compounds used according to the invention can in principle also be added during the preparation of the respective binders, ie in the course of their polymerization, polyaddition or polycondensation.
- the present invention also relates to an electrophotographic toner, Powder or powder coating containing a conventional binder, for example a Styrene, styrene acrylate, styrene butadiene, acrylate, urethane, acrylic, polyester or Epoxy resin or a combination of the last two, and 0.01 to 50% by weight, preferably 0.5 to 20% by weight, particularly preferably 0.1 to 5% by weight, in each case based on the total weight of the electrophotographic toner, powder or Powder coating, at least one inter-polyelectrolyte complex.
- a conventional binder for example a Styrene, styrene acrylate, styrene butadiene, acrylate, urethane, acrylic, polyester or Epoxy resin or a combination of the last two, and 0.01 to 50% by weight, preferably 0.5 to 20% by weight, particularly preferably 0.1 to 5% by weight, in each case based on the total weight of the electrophotographic toner, powder
- IPEC electrostatic separation processes of polymers and especially of (Salt) minerals can also be used externally by IPEC in the amounts specified above, d. H. on the surface of the material to be separated.
- the * mole data relate to average charge units, i.e. H. as "Monomer unit” is considered to be those sections that are just one charge carry. Percentages are percentages by weight.
- Table 2 below shows various analytical data using four of these compounds as examples of the IPEC used according to the invention.
- toner binders are used in the following application examples and carrier for use:
- IPEC 1 part of the respective IPEC is kneaded in 99 within 45 minutes Parts of a toner binder (styrene-methacrylate copolymer 60:40, resin 1, ®Dialec S 309) incorporated homogeneously. Then it is on a laboratory universal mill ground and then classified on a centrifugal sifter. The desired particle fraction (4 to 25 ⁇ m) is carried out with a carrier (Carrier 1) activated.
- Carrier 1 carrier activated.
- IPEC 1 part of the respective IPEC is mixed in within 45 minutes using a kneader 99 parts of a toner binder (biphenyl-based polyester, resin 2, ®Almacrylic resin) incorporated homogeneously. Then it is on a laboratory universal mill ground and then classified on a centrifugal sifter. The desired Particle fraction (4 to 25 ⁇ m) is activated with Carrier 2.
- a toner binder biphenyl-based polyester, resin 2, ®Almacrylic resin
- the measurement is carried out on a standard q / m measuring stand.
- the use of a sieve with a mesh size of 50 ⁇ m ensures that no carrier is entrained when the toner is blown out.
- the measurements are carried out at 50% relative air humidity.
- the q / m values ( ⁇ C / g] are measured as a function of the activation time.
- the q / m values are given in Table 3.
- the amounts of IPEC are each 1% by weight.
- 1 part of the compound from preparation example 6 was homogeneously incorporated into 99 parts of a powder coating binder (resin 1), as described for application examples 1 to 3.
- the tribo-spraying of the powders (varnishes) was carried out with a spray device, for example ®Tribo Star from Intec (Dortmund), with a standard spray tube and a star inner rod with maximum powder throughput with a spray pressure of 3 and 5 bar.
- the object to be sprayed was suspended in a spray booth and sprayed from a distance of about 20 cm directly from the front without further movement of the spraying device.
- the respective charge of the sprayed powder was then measured using a "measuring device for measuring triboelectric charge of powders" from Intec (Dortmund).
- the measuring antenna of the measuring device was held directly in the powder cloud emerging from the spraying device.
- the current strength resulting from the electrostatic charge of powder coating or powder was displayed in ⁇ A.
- the deposition rate was then determined in% by means of a differential weighing from sprayed and deposited powder coating.
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Developing Agents For Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Beim Corona-Verfahren wird der Pulverlack oder das Pulver an einer geladenen Corona vorbeigeführt und hierbei aufgeladen, beim triboelektrischen oder elektrokinetischen Verfahren wird vom Prinzip der Reibungselektrizität Gebrauch gemacht.
Im Falle von carboxyl- oder sulfogruppenhaltigen Polymeren kann es erforderlich sein, zur Erzeugung des Polyanions das Medium alkalisch zu stellen. Die erfindungsgemäß eingesetzten IPEC können im wesentlichen aus synthetischen und/oder natürlichen Polyanionen und aus synthetischen und/oder natürlichen Polykationen bestehen. Die Polyanionen oder Polykationen können auch Derivate von Naturstoffen sein.
Poly-(L)-Glutaminsäure, Poly-(L)-Asparaginsäure, saure Gelatine (A-Gelatine); Stärke-, Amylose-, Amylopektin-, Cellulose-, Guaran-, Gummi arabicum-, Gummi Karaya-, Gummi Guar-, Pullulan-, Xanthan-, Dextran-, Curdlan-, Gellan-, Carubin-, Agarose-, Chitin-, Chitosan-Derivate mit folgenden funktionellen Gruppen in verschiedenen Substitutionsgraden:
Carboxymethyl- und Carboxyethyl-, Carboxypropyl-, 2-Carboxyvinyl-, 2-Hydroxy-3-carboxypropyl-, 1,3-Dicarboxy-isopropyl-, Sulfomethyl-, 2-Sulfoethyl-, 3-Sulfopropyl-, 4-Sulfobutyl-, 5-Sulfopentyl-, 2-Hydroxy-3-sulfopropyl-, 2,2-Disulfoethyl-, 2-Carboxy-2-sulfo-ethyl-, Maleat-, Succinat-, Phthalat-, Glutarat-, aromatische und aliphatische Dicarboxylate-, Xanthogenat-, Sulfat-, Phosphat-, 2,3-Dicarboxy-, N,N-Di-(phosphatomethyl)-aminoethyl-, N-Alkyl-N-phosphatomethyl-aminoethyl-. Diese Derivate können daneben auch nichtionische funktionelle Gruppen in verschiedenen Substitutionsgraden enthalten, wie z. B. Methyl-, Ethyl-, Propyl-, Isopropyl-, 2-Hydroxyethyl-, 2-Hydroxypropyl-, 2-Hydroxybutyl-Gruppen sowie Ester mit aliphatischen Carbonsäuren (C2 bis C18).
die in US-A-5,500, 323 beschriebenen Polysulfondialkylammoniumsalze, erhältlich durch Copolymerisation von Salzen vorstehend genannten Dialkylammonium-Komponenten der Formel (I) mit Schwefeldioxid;
Poly-(L)-Lysin, Poly-(L)-Arginin, Poly(ornithin), basische Gelatine (B-Gelatine); Chitosan; Chitosan mit verschiedenen Acetylierungsgraden;
Stärke-, Amylose-, Amylopektin-, Cellulose-, Guaran-, Gummi arabicum-, Gummi Karaya-, Gummi Guar-, Dextran-, Pullulan-, Xanthan-, Curdlan-, Gellan-, Carubin-, Agarose-, Chitin-, Chitosan-Derivate mit folgenden funktionellen Gruppen in verschiedenen Substitutionsgraden:
- n =
- 5 bis 5x105;
- R1 =
- H oder CH3;
- X =
- O oder NH;
- A =
- verzweigte oder lineare Alkylene (C1 bis C18) oder Arylene, z. B. Phenylen oder Naphthylen;
- Y =
- NR2 2, N⊕R2 3 mit R2 = C1-C8-Alkyl; SO3 ⊖, COO⊖, Phosphat; N⊕R3 2-A-COO⊖, N⊕R3 2-A-SO3 ⊖, N⊕R3 2-A-PO(OH)O⊖ mit R3 = C1-C8-Alkyl;
- Z =
- Anion, z. B. Halogenid, Methylsulfat, Sulfat, Phosphat; oder Kation, z. B. Metall-Kation wie Na+ oder K+, oder quartäre Ammoniumverbindung;
100 mbar getrocknet.
- Harz 1:
- Styrol-Methacrylat-Copolymer 60:40
- Harz 2:
- Polyester auf Bisphenol-Basis (®Almacryl-Harz)
- Carrier 1:
- Mit Styrol-Methacrylat-Copolymer beschichtete Magnetit-Teilchen der Größe 50 bis 200 µm (Schüttdichte 2,62 g/cm3) (FBM 100 A; Fa. Powder Techn.).
- Carrier 2:
- Mit Silikon beschichtete Ferrit-Teilchen der Größe 50 bis 100 µm (Schüttdichte 2,75 g/cm3) (FBM 96-110; Fa. Powder Techn.)
Claims (9)
- Verwendung von Inter-Polyelektrolyt-Komplexen als Ladungssteuermittel und Aufladungsverbesserer in elektrophotographischen Tonern und Entwicklern, in triboelektrisch oder elektrokinetisch versprühbaren Pulvern und Pulverlacken und in Elektretmaterialien.
- Verwendung nach Anspruch 1, dadurch gekennzeichnet, daß der Inter-Polyelektrolyt-Komplex im wesentlichen aus einer oder mehreren Polyanionen-bildenden Verbindung(en) und aus einer oder mehreren Polykationen-bildenden Verbindung(en) besteht.
- Verwendung nach Anspruch 2, dadurch gekennzeichnet, daß das Molverhältnis von polymeren kationischen zu polymeren anionischen Gruppen im Inter-Polyelektrolyt-Komplex 0,9 : 1,1 bis 1,1 : 0,9 ist.
- Verwendung nach Anspruch 2 oder 3, dadurch gekennzeichnet, daß die Polyanionen-bildende(n) Verbindung(en) Poly(styrolsulfonsäure), Poly(acrylsäure), Poly(methacrylsäure), Poly(maleinsäure), Poly(itaconsäure), sulfatierter Poly(vinylalkohol), Poly(vinylsulfonsäure), Poly-(acrylsäure-co-maleinsäure), Poly(styrolsulfonsäure-co-maleinsäure), Poly(ethylen-co-acrylsäure), Poly(phosphorsäure), Poly(kieselsäure), Hectorit, Bentonit, Alginsäure, Pektinsäure, Carrageenan, Xanthan, Gummi arabicum, Dextransulfat, Carboxymethyldextran, Carboxymethyl-cellulose, Cellulosesulfat, Cellulosexanthogenat, Stärkesulfat, Stärkephosphat, Lignosulfonat, Gummi Karaya; Polygalakturonsäure, Polyglucuronsäure, Polyguluronsäure, Polymannuronsaure, Chondroitin-Sulfat, Heparin, Heparansulfat, Hyaluronsäure, Dermatansulfat, Keratansulfat, Poly-(L)-Glutaminsäure, Poly-(L)-Asparaginsäure, saure Gelatine (A-Gelatine); Stärke-Amylose-, Amylopektin-, Cellulose-, Guaran-, Gummi arabicum-, Gummi Karaya-, Gummi Guar-, Pullulan-, Xanthan-, Dextran-, Curdlan-, Gellan-, Carubin-, Agarose-, Chitin- oder Chitosan-Derivate mit folgenden funktionellen Gruppen:Carboxymethyl-, Carboxyethyl-, Carboxypropyl-, 2-Carboxyvinyl-, 2-Hydroxy-3-carboxypropyl-, 1,3-Dicarboxy-isopropyl-, Sulfomethyl-, 2-Sulfoethyl-, 3-Sulfopropyl-, 4-Sulfobutyl-, 5-Sulfopentyl-, 2-Hydroxy- 3-sulfopropyl-, 2,2-Disulfoethyl-, 2-Carboxy- 2-sulfo-ethyl-, Maleat-, Succinat-, Phthalat-, Glutarat-, aromatische und aliphatische Dicarboxylate-, Xanthogenat-, Sulfat-, Phosphat-, 2,3-Dicarboxy-, N,N-Di-(phosphatomethyl)-aminoethyl- und N-Alkyl-N-phosphatomethyl-aminoethyl,
- Verwendung nach einem oder mehreren der Ansprüche 2 bis 4, dadurch gekennzeichnet, daß die Polykationen-bildende(n) Verbindung(en) aus der Gruppe der Poly(alkylenimine); Poly-(4-vinyl-pyridin); Poly(vinylamin); Poly(2-vinyl-pyridin), Poly(2-methyl-5-vinyl-pyridin), Poly(4-vinyl-N-C1-C18-alkyl-pyridiniumsalz), Poly(2-vinyl-N-C1-C18-alkyl-pyridiniumsalz), Polyallylamin, aminoacetylierter Polyvinylalkohol; der polymeren Ammoniumsalze, erhältlich durch Homopolymerisation von Monomeren der Formel (I) worin die Reste R1 bis R12 unabhängig voneinander ein Wasserstoffatom, Hydroxyl, einen primären, sekundären oder tertiären Aminorest, einen Cyano- oder Nitrorest oder einen geradkettigen oder verzweigten, gesättigten oder ungesättigten C1-C18-Alkyl- oder C1-C18-Alkoxy-Rest bedeuten, und A- ein Anion bedeutet;
der Polysulfondialkylammoniumsalze, erhältich durch Copolymerisation von Monomeren der Formel (I) mit Schwefeldioxid;
Poly-(L)-Lysin, Poly-(L)-Arginin, Poly(ornithin), basische Gelatine (B-Gelatine); Chitosan; Chitosan mit verschiedenen Acetylierungsgraden; Stärke-, Amylose-, Amylopektin-, Cellulose-, Guaran-, Gummi arabicum-, Gummi Karaya-, Gummi Guar-, Dextran-, Pullulan-, Xanthan-, Curdlan-, Gellan-, Carubin-, Agarose-, Chitin- oder Chitosan-Derivate mit folgenden funktionellen Gruppen:2-Aminoethyl-, 3-Aminopropyl-, 2-Dimethylaminoethyl-, 2-Diethyl-aminoethyl-, 2-Diisopropylaminoethyl-, 2-Dibutylaminoethyl-, 3-Diethylamino-2-hydroxypropyl-, N-Ethyl-N-methylaminoethyl-, 2-Di-ethylhexyl-aminoethyl-, 2-Hydroxy-2-Diethylaminoethyl-, 2-Hydroxy-3-trimethylammoniono-propyl-, 2-Hydroxy-3-trimethyl-ammoniono-propyl-, 3-Trimethylammoniono-propyl-, 2-Hydroxy-3-pyridinium-propyl-, S,S-Dialkyl-thionium-alkyl; - Verwendung nach mindestens einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß der Inter-Polyelektrolyt-Komplex eine anionische und/oder kationische polymere Verbindung der Formel mit
- n =
- 5 bis 5x105;
- R1 =
- H oder CH3;
- X =
- O oder NA;
- A =
- verzweigte oder lineare Alkylene (C1 bis C18) oder Arylene, vorzugsweise Phenylen oder Naphthylen;
- Y =
- NR2 2, N⊕R2 3 mit R2 = C1-C8-Alkyl; SO3 ⊖, COO⊖, Phosphat; N⊕R3 2-A-COO⊖, N⊕R3 2-A-SO3 ⊖, N⊕R3 2-A-PO(OH)O⊖ mit R3 = C1-C8-Alkyl;
- Z =
- Anion, vorzugsweise Halogenid, Methylsulfat, Sulfat, Phosphat; oder Kation, vorzugsweise Metall-Kation wie Na+ oder K+, oder quartäre Ammoniumverbindung;
- Verwendung nach mindestens einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, daß der Interpolyelektrolyt-Komplex im wesentlichen aus einer Polyanionen-bildenden Verbindung aus der Gruppe Poly(styrolsulfonsäure), Poly(acrylsäure), Poly(methacrylsäure), Poly(vinylsulfonsäure), Poly(acrylsäure-co-maleinsäure), Polyphosphorsäure, Hectorit, Poly(styrolsulfonsäure-co-maleinsäure), Gummi arabicum, Carboxymethylcellulose, Xanthan, Carrageenan und Dextransulfat; und aus einer Polykationen-bildenden Verbindung aus der Gruppe Poly(diallyldimethylammonium), Chitosan, Diethylaminoethyldextran und Poly(ethylenimin) zusammengesetzt ist.
- Verwendung nach einem oder mehreren der Ansprüche 1 bis 7, dadurch gekennzeichnet, daß der Inter-Polyelektrolyt-Komplex in einer Konzentration von 0,01 bis 50 Gew.-%, vorzugsweise 0,5 bis 20 Gew.-%, bezogen auf die Gesamtmischung, in das Bindemittel des jeweiligen Toners, Entwicklers, Lacks, Pulverlacks oder Elektretmaterials eingearbeitet wird.
- Elektrophotographischer Toner, Pulver oder Pulverlack, enthaltend ein Styrol-, Styrolacrylat-, Styrolbutadien-, Acrylat-, Urethan-, Acryl-, Polyester- oder Epoxid-Harz oder eine Kombination der beiden letztgenannten, und 0,01 bis 50 Gew.-%, vorzugsweise 0,5 bis 20 Gew.-%, jeweils bezogen auf das Gesamtgewicht des elektrophotographischen Toners, Pulvers oder Pulverlacks, mindestens eines Inter-Polyelektrolyt-Komplexes gemäß einem der Ansprüche 1 bis 7.
Applications Claiming Priority (2)
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DE19732995A DE19732995A1 (de) | 1997-07-31 | 1997-07-31 | Verwendung von Inter-Polyelektrolyt-Komplexen als Ladungssteuermittel |
DE19732995 | 1997-07-31 |
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EP0895131A2 true EP0895131A2 (de) | 1999-02-03 |
EP0895131A3 EP0895131A3 (de) | 1999-12-22 |
Family
ID=7837485
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EP98113654A Withdrawn EP0895131A3 (de) | 1997-07-31 | 1998-07-22 | Verwendung von Inter-Polyelektrolyt-Komplexen als Ladungssteuermittel |
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US (1) | US6030738A (de) |
EP (1) | EP0895131A3 (de) |
JP (1) | JP3822365B2 (de) |
KR (1) | KR19990014297A (de) |
CN (1) | CN1209571A (de) |
BR (1) | BR9803725A (de) |
CA (1) | CA2244367A1 (de) |
DE (1) | DE19732995A1 (de) |
TW (1) | TW396299B (de) |
Cited By (1)
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EP1019174B1 (de) * | 1997-10-01 | 2005-06-08 | Minnesota Mining And Manufacturing Company | Methode zur herstellung von elektretartikelen und filter mit erhöhter ölnebelresistenz |
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DE19927835A1 (de) | 1999-06-18 | 2000-12-21 | Clariant Gmbh | Verwendung von verbesserten Cyanpigmenten in elektrophotographischen Tonern und Entwicklern, Pulverlacken und Ink-Jet-Tinten |
DE19957245A1 (de) * | 1999-11-27 | 2001-05-31 | Clariant Gmbh | Verwendung von salzartigen Struktursilikaten als Ladungssteuermittel |
DE10054344A1 (de) | 2000-11-02 | 2002-05-29 | Clariant Gmbh | Verwendung von gecoateten Pigmentgranulaten in elektrophotographischen Tonern und Entwicklern, Pulverlacken und Ink-Jet-Tinten |
DE60316117T2 (de) * | 2002-02-22 | 2008-05-29 | Kao Corp. | Reinigungsmittel mit antifoulingeigenschaften für harte oberflächen |
DE10235570A1 (de) | 2002-08-03 | 2004-02-19 | Clariant Gmbh | Verwendung von Salzen schichtartiger Doppelhydroxide |
DE10235571A1 (de) * | 2002-08-03 | 2004-02-12 | Clariant Gmbh | Verwendung von Salzen schichtartiger Doppelhydroxide als Ladungssteuermittel |
DE10251394A1 (de) | 2002-11-05 | 2004-05-13 | Clariant Gmbh | Blaues Farbmittel mit besonders hoher Reinheit und positiver triboelektrischer Steuerwirkung |
JP4532469B2 (ja) * | 2003-02-27 | 2010-08-25 | バテル・メモリアル・インスティテュート | 易脱墨性トナー粒子 |
WO2005007819A2 (en) | 2003-07-09 | 2005-01-27 | Wisconsin Alumni Research Foundation | Charge-dynamic polymers and delivery of anionic compounds |
BRPI0613649A2 (pt) * | 2005-07-21 | 2011-01-25 | Ciba Sc Holding Ag | complexos polieletrólitos como espessantes para soluções de sal com intensidade iÈnica elevada |
DE102007000806B3 (de) * | 2007-10-01 | 2009-04-30 | Institut für Holztechnologie Dresden gGmbH | Beschichtung für Holzmaterialien und Verfahren zu ihrer Herstellung |
US20090105375A1 (en) * | 2007-10-09 | 2009-04-23 | Lynn David M | Ultrathin Multilayered Films for Controlled Release of Anionic Reagents |
JP2009244494A (ja) * | 2008-03-31 | 2009-10-22 | Brother Ind Ltd | 負帯電トナーの製造方法 |
WO2015034357A1 (en) * | 2013-09-04 | 2015-03-12 | Ceradis B.V. | Paint composition comprising a polyelectrolyte complex |
US9857710B1 (en) * | 2016-09-07 | 2018-01-02 | Xerox Corporation | Support material comprising polyvinylalcohol and its use in xerographic additive manufacturing |
WO2018135626A1 (ja) * | 2017-01-23 | 2018-07-26 | 株式会社 資生堂 | 粉末含有組成物及びその製造方法、並びに化粧料 |
US10472500B2 (en) * | 2017-06-05 | 2019-11-12 | Purdue Research Foundation | Chitosan biopolymer and chitosan biopolymer based triboelectric nanogenerators |
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-
1997
- 1997-07-31 DE DE19732995A patent/DE19732995A1/de not_active Withdrawn
-
1998
- 1998-07-22 EP EP98113654A patent/EP0895131A3/de not_active Withdrawn
- 1998-07-29 TW TW087112478A patent/TW396299B/zh not_active IP Right Cessation
- 1998-07-30 CN CN98117847A patent/CN1209571A/zh active Pending
- 1998-07-30 US US09/126,204 patent/US6030738A/en not_active Expired - Fee Related
- 1998-07-30 BR BR9803725-0A patent/BR9803725A/pt not_active Application Discontinuation
- 1998-07-30 KR KR1019980030822A patent/KR19990014297A/ko not_active Application Discontinuation
- 1998-07-30 JP JP21610698A patent/JP3822365B2/ja not_active Expired - Lifetime
- 1998-07-30 CA CA002244367A patent/CA2244367A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
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US6030738A (en) | 2000-02-29 |
JPH11124565A (ja) | 1999-05-11 |
CA2244367A1 (en) | 1999-01-31 |
CN1209571A (zh) | 1999-03-03 |
JP3822365B2 (ja) | 2006-09-20 |
EP0895131A3 (de) | 1999-12-22 |
KR19990014297A (ko) | 1999-02-25 |
DE19732995A1 (de) | 1999-02-04 |
TW396299B (en) | 2000-07-01 |
BR9803725A (pt) | 1999-11-03 |
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