WO2011147892A1 - Utilisation de pigments à effet à surface modifiée, dans un agent de revêtement exempt de solvant, agent de revêtement exempt de solvant et objet revêtu - Google Patents

Utilisation de pigments à effet à surface modifiée, dans un agent de revêtement exempt de solvant, agent de revêtement exempt de solvant et objet revêtu Download PDF

Info

Publication number
WO2011147892A1
WO2011147892A1 PCT/EP2011/058593 EP2011058593W WO2011147892A1 WO 2011147892 A1 WO2011147892 A1 WO 2011147892A1 EP 2011058593 W EP2011058593 W EP 2011058593W WO 2011147892 A1 WO2011147892 A1 WO 2011147892A1
Authority
WO
WIPO (PCT)
Prior art keywords
effect pigments
modified
containing compound
epoxide
pigments
Prior art date
Application number
PCT/EP2011/058593
Other languages
German (de)
English (en)
Inventor
Michael GRÜNER
Thomas Schneider
Burkhard Schreiber
Günter KAUPP
Ulrich Schmidt
Dirk Schumacher
Christian Wolfrum
Original Assignee
Eckart Gmbh
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 Eckart Gmbh filed Critical Eckart Gmbh
Priority to EP11724151.3A priority Critical patent/EP2576702A1/fr
Publication of WO2011147892A1 publication Critical patent/WO2011147892A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/0015—Pigments exhibiting interference colours, e.g. transparent platelets of appropriate thinness or flaky substrates, e.g. mica, bearing appropriate thin transparent coatings
    • C09C1/0021—Pigments exhibiting interference colours, e.g. transparent platelets of appropriate thinness or flaky substrates, e.g. mica, bearing appropriate thin transparent coatings comprising a core coated with only one layer having a high or low refractive index
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/0015—Pigments exhibiting interference colours, e.g. transparent platelets of appropriate thinness or flaky substrates, e.g. mica, bearing appropriate thin transparent coatings
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C2200/00—Compositional and structural details of pigments exhibiting interference colours
    • C09C2200/10—Interference pigments characterized by the core material
    • C09C2200/1004—Interference pigments characterized by the core material the core comprising at least one inorganic oxide, e.g. Al2O3, TiO2 or SiO2
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C2200/00—Compositional and structural details of pigments exhibiting interference colours
    • C09C2200/10—Interference pigments characterized by the core material
    • C09C2200/102—Interference pigments characterized by the core material the core consisting of glass or silicate material like mica or clays, e.g. kaolin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C2200/00—Compositional and structural details of pigments exhibiting interference colours
    • C09C2200/10—Interference pigments characterized by the core material
    • C09C2200/1054—Interference pigments characterized by the core material the core consisting of a metal
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C2200/00—Compositional and structural details of pigments exhibiting interference colours
    • C09C2200/40—Interference pigments comprising an outermost surface coating
    • C09C2200/401—Inorganic protective coating
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C2200/00—Compositional and structural details of pigments exhibiting interference colours
    • C09C2200/40—Interference pigments comprising an outermost surface coating
    • C09C2200/402—Organic protective coating

Definitions

  • the surface-modified effect pigments can be used in a powder coating as well as in toners.
  • Powder coatings are considered to be an ideal solvent-free coating systems with regard to ever stricter environmental regulations, such as VOC guidelines, in many
  • Powder coatings are used, for example, in the painting of vehicle parts, garden furniture, camping articles, household appliances,
  • Refrigerators or shelves used. For the most part, metallic objects are painted, but painting of e.g.
  • the powder technology is based on the principle of electrostatic charging, whereby the electrostatic charging of the powder coating
  • the powder paint is charged via at least one electrode integrated in the powder paint pasteurization.
  • the powder coating passes on the one hand by the conveying air of the powder paint gun and on the other hand by the air movement in the application cabin, caused by the
  • the applied powder coating is melted by supplying thermal energy and subsequently cured. Excess powder coating, which does not adhere to the substrate to be coated, can be recycled and reused. Since this so-called overspray is usually finer than the powder coating originally used, the overspray is blended with not yet used powder coating to a stable
  • Powder coatings can to achieve different colors and / or optical effects with organic or inorganic colorants and / or
  • platelet-shaped effect pigments such as metal effect pigments or
  • powder coating resins are provided, for example, with organic or inorganic pigments, these are combined with others
  • Powder coating components such as hardeners, additives or fillers, extruded after mixing and after further process steps for
  • Flake-form effect pigments such as metal effect pigments or pearlescent pigments, are normally not incorporated into a powder coating in this manner. They are destroyed by the applied shear forces and thus do not give any visual
  • Name powder spray gun Such agglomerates are entrained from a certain size of the conveying air and lead to hitting on the substrate to be coated to Lackierêtn, so a
  • platelet-shaped effect pigments can be incorporated into powder coatings by the so-called bonding method.
  • the powder coating technology it is possible to apply coating layers with higher layer thicknesses than with conventional coating methods, which may be advantageous in terms of chemical and physical resistance.
  • the layer thickness also influences, for example, the accuracy of fit in the assembly of
  • EP 1 339 806 B1 describes a powder coating composition comprising a resin support and a pigment.
  • the pigment is first cast with alumina or a mixture of cerium and
  • Aluminum oxides and a silane coupling agent coated can either be applied to the first layer or be present as a mixed layer with this.
  • pearlescent pigments suitable for use in powder coatings (“powder coating precursors") are known. These are synthesized according to the periginous pigments described in EP 1 339 806 B1, in which case additionally on the surface of the silane coupling agent, e.g.
  • Alumina which is usually added as a giant powder coatings, is present.
  • the silane coupling agent is present as a separate layer.
  • WO 2006/136435 A2 relates to a method, preferably a
  • Spray-drying process for the preparation of periginous pigments, which with a non-cured, chemically crosslinkable and / or under
  • Electron-beam crosslinkable oligomeric and / or polymeric binder are coated.
  • Such pearlescent pigments are characterized by a high flexibility in the application.
  • Pulveriacken it is particularly advantageous if the coating of the pigment is identical to the Binder of the powder coating is, so that it comes after application and curing of Pulveriacks to form a homogeneous paint layer in which the pearlescent pigments are chemically incorporated.
  • paint layers opposite
  • WO 2005/063897 A2 relates to metallic effect pigments prepared by the process according to the teaching of WO 2006/136435 A2.
  • Digiycidylpolysiloxane compound surface-treated pigments are known from EP 0 764 191 B1. This surface treatment is intended to settle and agglomerate the pigments in liquid
  • Prevent coating agents such as in a paint or an ink.
  • Polymer-coated pearlescent and metallic pigments are known from EP 2 098 574 A2.
  • the polymer layer is a prepolymer over a
  • Coupling reagent covalently bonded to the at least one metal oxide layer of the pigment.
  • WO 98/46682 A1 describes powder coating compositions which contain metal or pearlescent pigments. To a more even
  • the pigments are treated with a viscous liquid so that the pigments have a sticky surface. After mixing with the powder coating, the powder coating adheres to the sticky surface of the pigments.
  • Coating center allow the provision of a coated article with a visually pleasing appearance without defects in the coating. They are intended for powder coatings in indoor and / or
  • Powder-coated building facades should be distinguished by their good ability to disguise and weather stability.
  • When used as a toner should give a uniform print image.
  • At least one optional protective layer can be arranged on the dielectric layer, and the effect pigments on the effect pigment surface are surface-modified with at least one epoxide group-containing compound, with the proviso that the at least one epoxide group-containing compound contains no silicon atoms.
  • Preferred developments are specified in the dependent claims 2 to 11.
  • the object on which the invention is based is also achieved by providing surface-modified effect pigments comprising platelet-shaped substrates with at least one dielectric layer, wherein at least one optional layer is provided on the at least one dielectric layer
  • Protective layer may be arranged, wherein the effect pigments on the
  • At least one epoxide group-containing compound does not contain silicon atoms, and the surface-modified effect pigments have a specific epoxide equivalent weight ranging from 119,000 to 800, based on the total weight of the surface-modified effect pigments.
  • the object of the invention is also achieved by providing a
  • solvent-free coating agent comprising surface-modified effect pigments dissolved, the surface-modified effect pigments having a platelet-shaped substrate and at least one dielectric layer, wherein at least one optional protective layer can be arranged on the at least one dielectric layer, and the effect pigments on the effect pigment surface are surface-modified with at least one epoxide group-containing compound, with the proviso that the
  • At least one epoxide group-containing compound contains no Siiiziumatome.
  • Coating agent is coated.
  • coated with a powder paint objects are preferably facade elements, vehicle parts, bodies,
  • the at least one epoxide group-containing compound is selected from the group consisting of:
  • the epoxide group-containing compounds to be used according to the invention do not comprise any
  • silanes containing epoxide groups and / or siloxanes or polysiloxanes containing epoxide groups are mentioned, but with what
  • Silicon atom (s) are meant.
  • effect pigments used preferably have no silanes, such as alkyl silanes, as a surface modification.
  • Powder coatings comprising the surface-modified effect pigments to be used according to the invention have in the
  • the solvent-free coating agent is a powder coating or a toner.
  • Coating agents are included.
  • a toner is understood to mean a dry toner whose
  • Solvent content is at most 3 wt .-%, preferably at most 1 wt .-% is. According to a further preferred embodiment, the content of solvent in the dry toner is at most 0.5% by weight. According to another preferred embodiment, the dry toner contains no
  • the Pulveriack invention preferably contains no solvent.
  • the invention relates in particular to powder coatings which are prepared by the dry biend process and which contain the surface-modified effect pigments to be used according to the invention.
  • the metals of the metallic platelet-shaped substrates may be selected from the group consisting of aluminum, copper, zinc, iron, titanium, stainless steel, silver, their alloys, and mixtures thereof.
  • the metals of the metallic platelet-shaped substrates are selected from the group consisting of aluminum, copper, zinc, iron, stainless steel, their alloys and mixtures thereof.
  • the metals of the metallic platelet-shaped substrates are particularly preferably selected from the group consisting of aluminum, copper, zinc, iron, their alloys and mixtures thereof.
  • the metals of the metallic substrates are selected from the group consisting of
  • Aluminum platelets are particularly preferably used as metallic platelet-shaped substrates.
  • the non-metallic platelet-shaped substrates are preferably substantially transparent, preferably transparent, i. for visible light, they are at least partially permeable. Under partially becomes permeable
  • the transmission at least 50%, further preferably at least 70%, more preferably at least 90%, in each case based on the incident light.
  • the non-metallic platelet-shaped substrates may be selected from the group consisting of natural mica platelets, synthetic
  • non-metallic platelet-shaped substrates comprising an inorganic-organic mixed layer are selected.
  • non-metallic platelet-shaped substrates may be glass flakes coated on both sides with semitransparent metal layers selected from the group consisting of silver, aluminum, chromium, nickel, gold, platinum, palladium, copper, zinc, titanium, their alloys, and mixtures thereof , be used.
  • semitransparent metal layers selected from the group consisting of silver, aluminum, chromium, nickel, gold, platinum, palladium, copper, zinc, titanium, their alloys, and mixtures thereof , be used.
  • effect pigments it is also possible to use those whose substrates are mixtures of the platelet-shaped substrates indicated above.
  • the non-metallic platelet-shaped substrates are selected from the group consisting of natural mica platelets, synthetic
  • the non-metallic platelet-shaped substrates are selected from the group consisting of natural mica platelets, synthetic mica platelets, glass flakes, and mixtures thereof. Very particular preference is given to natural and synthetic mica flakes and their mixtures as substrates.
  • natural mica platelets are preferred as the substrate.
  • the usable as a substrate glass flakes for example, a
  • composition according to the teaching of EP 1 980 594 B1.
  • the surface-modified effect pigments which can be used for the inventive use in solvent-free coating systems, in particular powder coatings, are prepared by forming the platelet-shaped substrates with at least one dielectric
  • the at least one dielectric charge, the optionally present at least one protective layer and the surface modification with at least one epoxide group-containing compound can each independently completely envelop the platelet-shaped substrate or be present only partially on the platelet-shaped substrate.
  • the surface-modified effect pigments are preferably distinguished by a uniform, homogeneous structure of each of these layers.
  • each layer preferably envelops the platelet-shaped substrate or the correspondingly already precoated substrate substantially completely, preferably completely.
  • the surface modification with at least one epoxide group-containing compound can each independently completely envelop the platelet-shaped substrate or be present only partially on the platelet-shaped substrate.
  • the surface-modified effect pigments are preferably distinguished by a uniform, homogeneous structure of each of these layers.
  • each layer preferably envelops the platelet-shaped substrate or the correspondingly already precoated substrate substantially completely, preferably completely.
  • the surface modification with at least one epoxide group-containing compound can each independently completely e
  • the at least one dielectric layer of the surface-modified effect pigments is preferably arranged directly on the platelet-shaped substrate. If at least one protective layer is arranged on the at least one dielectric layer, then the protective layer is between the at least one dielectric layer and the second
  • the effect pigment surface is surface-modified with the at least one epoxide group-containing compound, the epoxide group-containing compound is disposed on the outside.
  • the at least one epoxide group-containing compound is preferably present in a layer, preferably at least partially enveloping the effect pigment surface.
  • the effect pigment to be used according to the invention comprises only a single dielectric layer, which is applied directly to the platelet-shaped substrate.
  • the effect pigment to be used according to the invention comprises only a single dielectric layer, which is applied directly to the platelet-shaped substrate, and a single protective layer, which is applied directly to the dielectric layer.
  • the epoxide group-containing compound is applied directly to the protective layer and at least partially enveloping it.
  • the effect pigment to be used according to the invention has two, three, four, five, six or more
  • the dielectric layers are preferably applied directly following one another.
  • the at least one optional protective layer is preferably disposed externally with respect to the dielectric layers, so that the
  • the layer form of dielectric layers is arranged alternately with respect to the refractive index.
  • the alternately arranged high and low refractive dielectric layers directly on the substrate, the optional protective layer directly on said Schichtfoige and the epoxide group-containing compound directly on the optional protective layer or directly on said layer sequence are arranged.
  • the layer form of alternating high and low refractive dielectric layers preferably starts and ends with a high refractive index layer, so that on the
  • a dielectric layer is understood as meaning a coating which is not or slightly electrically conductive, ie a layer having a specific resistance of 1-10 4 ohm and greater. Reference may be made to literature values for known substances.
  • the dielectric layer it is preferable to apply layers comprising metal oxides, metal oxide hydrates, metal hydroxides, metal suboxides,
  • the dielectric coating consists of the abovementioned materials.
  • the dielectric layer may comprise or consist of only a single one of these compounds.
  • the dielectric layer may also comprise several of the compounds listed above in the same layer.
  • the dielectric layer may comprise at least two different metal oxides or a metal oxide and a metal hydroxide of one or more metals.
  • the dielectric layer may thus comprise at least two of the compounds listed above as a mixture in the same layer or as separate layers.
  • Metal oxides, metal oxide hydrates, metal hydroxides, organic dielectric materials and / or mixtures thereof are preferably used as the dielectric layer. Particular preference is given to using metal oxides and metal oxide hydrates and / or mixtures thereof. Furthermore, it is preferred that the dielectric layer is not an inorganic / organic mixed layer according to DE 10 2006 009 131 A1.
  • organic dielectric materials are understood as meaning organic monomers and polymers. These include, inter alia, acrylates, polyethers, polyamides, (poly) urethanes, Polyoiefine, isocyanates, latex or cellulose derivatives. Preferably, acrylates and / or polyethers are used.
  • the dielectric layer may include a high refractive index layer
  • the dielectric layer may be an optically active layer.
  • dielectric high-index layer for example, are examples of materials that are present in the dielectric high-index layer.
  • Metal oxides such as titanium oxide, preferably titanium dioxide (TiO 2 ), iron oxide, preferably iron (IN) oxide (Fe 2 O 3 ), zinc oxide preferably ZnO, tin oxide, preferably tin dioxide (SnO 2), zirconium oxide, preferably
  • Metal oxides such as Fe 2 0 3 doped Ti0 2 and / or mixtures thereof.
  • the dielectric high-index layer particularly preferably comprises titanium dioxide, iron (III) oxide, goethite, ilmenite,
  • the dielectric high-index layer comprises titanium dioxide, iron (III) oxide and / or mixtures thereof.
  • the dielectric high-index layer consists of the abovementioned compounds or mixtures thereof.
  • the titanium dioxide can be modified in the rutile or anatase crystal modification available.
  • the titanium dioxide layer is in the rutiiform.
  • the rutile form can be obtained, for example, by applying a layer of tin dioxide to the platelet-shaped substrate to be coated, for example, before application of the titanium dioxide layer. On this layer of tin dioxide, titanium dioxide crystallizes in the rutile modification.
  • the tin dioxide may be present as a separate layer, wherein the layer thickness may be a few nanometers, for example less than 10 nm, more preferably less than 5 nm, even more preferably less than 3 nm.
  • the tin dioxide can also be present at least partially in admixture with the titanium dioxide.
  • dielectric low-refraction layers include metal oxides such as silicon oxide, preferably silicon dioxide (S1O2), aluminum oxide, preferably aluminum (III) oxide (Al 2 O 3 ), boron oxide, preferably B2O3,
  • Metailfluoride such as magnesium fluoride, preferably MgF 2 , aluminum fluoride, preferably AIF 3 , cerium fluoride, preferably CeF 3 , calcium fluoride,
  • metal oxide hydrates such as alumina hydrate AIO (OH), silica hydrate, organic monomers and polymers consisting of, for example, acrylates or methacrylates and / or mixtures of the abovementioned compounds.
  • the dielectric low-index layer preferably comprises silicon dioxide, silicon oxide hydrate, aluminum oxide, aluminum oxide hydrate and / or acrylates.
  • the dielectric low refractive index layer is silicon dioxide
  • the dielectric low-index layer particularly preferably comprises silicon dioxide and / or silicon oxide hydrate.
  • at least one protective layer can furthermore be applied to the at least one dielectric coating.
  • the protective layer can on the one hand
  • Metal oxide hydrates and / or metal hydroxides include.
  • the protective layer may comprise organic polymers consisting of, for example, acrylates or polyethers.
  • the at least one protective layer comprises metal oxides, metaoxide hydrates and / or metal hydroxides of chromium, cerium and / or silicon.
  • the at least one protective layer comprises metal oxides, metal oxide hydrates and / or metal hydroxides of silicon and / or organic polymers.
  • the at least one protective layer preferably comprises metal oxides, metaoxide hydrates and / or metal hydroxides of chromium, cerium and / or silicon.
  • the at least one protective layer preferably comprises silicon dioxide, silicon oxide hydrate and / or acrylates. In a further embodiment, the
  • the at least one protective layer may comprise a single one of the aforementioned compounds.
  • the at least one protective layer may also comprise several of these compounds, which may be present as a mixture or as discrete layers, which preferably follow one another directly.
  • the protective layer may at least partially form the dielectric layer to form a mixed layer
  • Effect pigment surface i. on the dielectric layer or the optional protective layer, at least one compound having epoxide groups. Accordingly, mixtures of different epoxide group-containing compounds can also be present.
  • the epoxide group-containing compound has at least one epoxide group in the molecule. This can be added to saturated or unsaturated, branched or unbranched, substituted or unsubstituted aliphatic or
  • the epoxide group may be bonded in the molecule via at least one free carboxylic, sulfonic or phosphonic acid group or at least one free hydroxyl group.
  • the epoxy group-containing compound may have both mono- and di-substituted epoxy groups in the molecule.
  • substituted epoxide groups are to be understood as those which carry only one radical other than hydrogen.
  • different moieties of the di-substituted epoxy groups can be in both the 1, 1 and 1, 2 positions.
  • the non-hydrogen radicals of the di-substituted epoxide groups are in the 1, 2-position.
  • Epoxy group in the molecule include 1, 2-epoxy-3-methoxypropane (930-37-0), 1, 2-epoxy-3-ethoxypropane (4016-11-9), 1, 2-epoxy-3-propoxypropane (3126-95-2), 1,2-epoxy-3-isopropoxypropane (4016 14-2), 3-butoxy-1,2-epoxypropane (2426-08-6), 3-tert-butoxy-1,2-epoxypropane (7665-72-7), 1, 2-epoxy-3- ( isopentyloxy) propane (15965-97-6), 1,2-epoxy-3- (hexyloxy) propane (5926-90-9), 1,2-epoxy-3- [2- (ethylhexyl) oxypropane (2461-
  • 1,2-Epoxy-3-methoxypropane (930- 37-0), 1,2-epoxy-3-ethoxypropane (4016-11-9), 1, 2-epoxy-3-ethoxypropane (1), 2-epoxy-3-ethoxypropane (1), 2-epoxy-3-propoxypropane (3126-95-2), 1,2-epoxy-3-isopropoxypropane (4016-14-2), 3-tert-butoxy-1,2-epoxypropane (7665-72-7) , 1,2-epoxy-3- (isopentyloxy) propane (15965-97-6),
  • epoxy group-containing compounds which have only one epoxide group in the molecule, 1,2-epoxy-3-methoxypropane (930-37-0), 1,2-epoxy-3-ethoxypropane (4016-11-9), 1 , 2-epoxy-3-propoxypropane (3126-95-2), 1, 2-epoxy-3-isopropoxypropane (4016-14-2), 3-tert- Butoxy-1,2-epoxypropane (7665-72-7), 1- (Cyciohexyloxy) -2,3-epoxypropane (3681-02-5), [(Vinyloxy) methyl] oxirane (3678-15-7), 1 -Allyloxy-2,3-epoxypropane (106-92-3), 2,3-epoxypropyl propargyl ether (18180-30-8), 1,2-epoxy-3- (4-viny1benzyloxy) propane (113538-80- 0), 2,3-epoxypropyl
  • the epoxide group-containing compound has at least two epoxide groups in the molecule.
  • covalent attachment of the epoxide group-containing compound can take place by reacting an epoxide group with the effect pigment surface, for example a hydroxyl group on the effect pigment surface.
  • the at least one further epoxy group can then in the powder coating a covalent bond with the
  • the epoxide group-containing compounds which have at least two epoxide groups in the molecule include, for example, bis (2,3-epoxypropyl) ether (2238-07-5), 1,2-bis (2,3-epoxypropoxy) ethane (2,224- 15-9), 1,4-bis (2,3-epoxypropoxy) butane (2425-79-8), 1,3-bis (2,3-epoxypropoxy) butane (3332-48-7), 1, 5 Bis (2,3-epoxypropoxy) pentane (7517-06-8), 1, 3-bis (2,3-epoxypropoxy) -2,2-dimethylpropane (17557-23-2), 1, 6-bis ( 2,3-epoxypropoxy) - hexane (16096-31-4), 1,2-bis (2 : 3-epoxypropoxy) cyclohexane (37763-26-1), 1,4-bis [(2,3-epoxypropoxy) methyl] cyclohexane (142
  • epoxide group-containing compounds which have at least two epoxide groups in the molecule, bis (2,3-epoxypropyl) ether (2238-07-5), 1,3-bis (2,3-epoxypropoxy) butane (3332-48 -7), 1,5-bis (2,3-epoxypropoxy) pentane (7517-06-8), 1,2-bis (2,3-epoxypropoxy) cyclohexane (37763-26-1), 1, 3 Bis (oxiran-2-ylmethoxy) propan-2-ol (3568-29-4), bis [2- (2,3-epoxypropoxy) ethyl] ether (4206-61-5), 2,2 '- [oxybis [(methyl-2,1-ethanediyl) oxymethylene]] bisoxirane (41638-13-5), 1,2,3-tris (2,3-epoxypropoxy) propane (13236-02-7), 2- [3 - [1,3-bis [3
  • epoxide group-containing compounds which have at least two epoxide groups in the molecule, bis (2,3-epoxypropyl) ether (2238-07-5), 1,3-bis (2,3-epoxypropoxy) butane (3332-48 -7), 1, 5-bis (2,3-epoxypropoxy) pentane (7517-06-8), 1,2,3-tris (2,3-epoxypropoxy) propane (13236-02-7), 2 , 6-bis (2,3-epoxypropyl) phenyl-2,3-epoxypropyl ether (13561-08-5), bis (oxirane-2-ylmethyl) oxalate (60468-47-5), bis (2,3-epoxy pyrolylmonate (60468-48-6), bis (2,3-epoxypropyl) -2,2-dimethylmuthate (25677-88-7), bis (2,3-epoxycyclohexylmethyi
  • a mixture of different epoxide group-containing compounds is applied to the purelypigmentoberfikiee.
  • epoxide group-containing compound no silane-functional group.
  • Pigments which are surface-modified with epoxide group-containing compounds having in addition to the epoxide group at least one silane-functional group in the molecule are not compatible with the surrounding powder coating for reasons not yet understood.
  • Pigment agglomerates on the substrate to be coated and a concomitant, insufficient recyclability of overspray are the result. Furthermore, powder coatings which contain such surface-modified effect pigments contain an insufficient coating of the substrate edges during application, which leads to an increased
  • the epoxide group-containing compound can be applied to the dielectric layer or the optional protective layer by the at least one epoxide group-containing compound with the respective
  • Effect pigment is optionally mixed in the presence of a solvent and then dried.
  • 10% by weight, based on the total weight of the surface-modified effect pigment, of at least one compound containing epoxide groups is applied to the dielectric layer or the optionally present protective layer.
  • the amount of the at least one epoxy group-containing compound used is in a range of 0.5 to 8 wt%, more preferably in a range from 0.6 to 6 wt .-%, particularly preferably in a range of 0.7 to 5 wt .-% and most preferably in a range of 0.8 to 4% by weight, each based on the total weight of surface-modified effect pigments.
  • the epoxide group-containing compound is not applied to the dielectric layer or the optional protective layer by the spray-drying method.
  • the spray-drying process is described in WO 2006/136435 A2 or in WO 2005/063897 A2.
  • the epoxide group-containing compound can have at least one
  • Epoxy group bound to the dielectric layer or the optional protective layer it is preferred that at least part of the epoxide groups of the at least one epoxide group-containing compound remain on the effect pigment surface in order to allow a reaction with the powder coating components.
  • Each free epoxide group can be used for further crosslinking of the epoxide group-containing
  • Compounds serve each other and / or for reaction with the binder component of the powder coating.
  • the at least one epoxide group-containing compound is preferably applied directly to the pigment surface, i. without coupling reagent applied.
  • the pigments to be used according to the invention therefore have a surprisingly simple structure.
  • the epoxide group-containing compounds have a
  • Epoxy equivalent weight in the range of 10 to 20,000.
  • the epoxy group-containing compounds have a Epoxidäquivalientwhen in the range of 15 to 15,000 and more preferably in the range of 20 to 10,000.
  • Most particularly preferred exhibit the epoxide group-containing compounds an epoxide equivalent weight ranging from 22 to 7,000 or from 30 to 800.
  • the epoxide equivalent weight is understood to mean that amount of epoxide group-containing compound in grams which contains 16 grams of epoxide-bonded oxygen (epoxide oxygen).
  • the determination is carried out, as known to those skilled in the art, by titration with cetyltrimethylammonium bromide under acidic conditions.
  • the effect pigments surface-modified with an epoxide group-containing compound have a specific epoxide equivalent weight in a range from 119,000 to 800, preferably from a range from 115,000 to 900, and more preferably from a range from 114,000 to 1,000. With very particular preference the surface-modified effect pigments have a specific epoxide equivalent weight in the range from 106,000 to 2,500.
  • the specific epoxide equivalent weight is understood to mean the amount of pigment in grams which contains 16 grams of epoxide oxygen (epoxide oxygen).
  • the determination of the specific epoxide equivalent weight is carried out in accordance with the determination of the epoxide equivalent weight of the compound containing epoxide groups by titration. This must additionally the Amine number of Vietnamese devisfi Stahlenmod en effect pigment can be determined.
  • the average diameter of the effect pigments, indicated as D 50 of the surface-modified effect pigments, is preferably in a range from 2.0 ⁇ m to 100 ⁇ m, preferably in a range from 2.5 ⁇ m to 75 ⁇ m, more preferably in a range of 3.0 ⁇ to 50 ⁇ , more preferably in a range of 3.5 ⁇ to 35 ⁇ and most preferably in a range of 4.2 to 24 ⁇ .
  • the Dgo value of the diameter of the effect pigments is preferably in a range from 8 to 290 ⁇ , more preferably in a range from 10 to 240 ⁇ , even more preferably in a range from 19 to 155 ⁇ , more preferably in a range of 24 to 90 ⁇ and most preferably in a range of 16 to 47 ⁇ .
  • volume-average size distribution function as obtained by laser diffraction methods, indicates that 10%, 50%, and 90%, respectively, of the surface-modified effect pigments have a diameter equal to or less than the specified value.
  • the size distribution curve of the effect pigments based on non-metallic, platelet-shaped substrates is measured using a device from Malvern (device:
  • the present invention comprises the use of surface-modified pearlescent pigments in a powder coating, wherein the surface-modified pearlescent pigments based on a platelet-shaped transparent substrate comprise at least one dielectric layer, optionally at least one protective layer, and a surface modification with at least one epoxide group-containing compound.
  • the present invention comprises the use of surface-modified pearlescent pigments in a powder coating, wherein the surface-modified pearlescent pigments based on a platelet-shaped transparent substrate comprise at least one optically active layer, optionally at least one protective layer, and a
  • the present invention comprises the use of surface-modified pearlescent pigments in a powder coating, wherein the surface-modified pearlescent pigments based on flake-form natural or synthetic mica comprise at least one dielectric layer consisting of metal oxides and / or metal oxide hydrates, optionally at least one protective layer, and a
  • the present invention comprises the use of surface-modified pearl pigments in a powder coating, wherein the surface-modified pearlescent pigments based on flake-form natural or synthetic mica comprise at least one dielectric layer, optionally at least one protective layer consisting of metal oxides and / or metal hydroxides, and a surface modification comprising at least one epoxide group-containing compound having at least two epoxide groups.
  • the present invention comprises the use of surface-modified pearlescent pigments in a powder coating, wherein the surface-modified pearlescent pigments based on flake-form natural or synthetic mica comprise at least one dielectric layer consisting of metal oxides and / or metal hydroxides, optionally at least one protective layer consisting of metal oxides,
  • Metal oxide hydrates and / or metal hydroxides, as well as a surface modification with at least one epoxide group-containing compound having at least two epoxide groups, without silicon atoms in the molecule include.
  • the present invention comprises the use of surface-modified pearlescent pigments in a powder coating, wherein the surface-modified pearlescent pigments based on a platelet-shaped substrate comprise at least one dielectric layer, optionally at least one protective layer, and a surface modification with at least one epoxide group-containing compound, and wherein the surface-modified pearlescent pigments specific epoxide equivalent weight ranging from 119,000 to 800.
  • the present invention comprises the use of surface-modified pearlescent pigments in a powder coating, wherein the surface-modified pearlite pigments based on glass flakes comprise at least one dielectric layer, optionally at least one protective layer, and a surface modification with at least one epoxide group-containing compound.
  • the present invention comprises the use of surface-modified pearlite pigments in a powder coating, wherein the surface-modified pearlite pigments based on glass flakes comprise at least one dielectric layer, optionally at least one protective layer consisting of metal oxides, metal oxide hydrates and / or metal hydroxides, and a surface modification with at least one epoxy group-containing Compound with at least two epoxide groups.
  • the present invention comprises the use of surface-modified metallic effect pigments in one
  • the surface-modified metallic effect pigments based on a platelet-shaped substrate comprise at least one dielectric layer, optionally at least one protective layer, as well as a surface modification with at least one epoxide group-containing compound.
  • the present invention comprises the use of surface-modified metallic effect pigments in one
  • the surface-modified metallic effect pigments based on a platelet-shaped substrate comprise at least one dielectric layer, optionally at least one protective layer, and a surface modification with at least one epoxide group-containing compound having at least two epoxide groups.
  • the present invention comprises the use of surface-modified metallic effect pigments in one
  • Powder coating wherein the surface-modified metallic effect pigments based on piuschtigenförmigem aluminum comprise at least one dielectric layer, optionally at least one protective layer, and an outer layer having at least one epoxide group-containing compound.
  • the present invention comprises the use of surface-modified metallic effect pigments in one
  • Powder coating wherein the surface-modified metallic effect pigments based on contemplatl aluminum comprise at least one dielectric layer, optionally at least one protective layer, as well as a surface modification with at least one epoxide group-containing compound having at least two epoxide groups.
  • the present invention comprises the use of surface-modified metallic effect pigments in one
  • Powder coating wherein the surface-modified metallic effect pigments based on respect to hypothetical aluminum at least one dielectric layer, consisting of an acrylic, optionally at least one
  • Protective layer as well as a surface modification with at least one epoxide group-containing compound.
  • the present invention comprises the use of surface-modified metallic effect pigments in one
  • the surface-modified metallic effect pigments based on pi2011förmigem aluminum at least one dielectric layer consisting of Stiiziumdioxid and / or Siliziumoxidhydrat, optionally at least one protective layer consisting of an acrylic, and a surface modification with at least one epoxy group-containing Compound having at least two epoxy groups, which contains no Siüziumatome in the molecule include.
  • the present invention comprises the use of surface-modified metal effect pigments in one
  • Powder paint wherein the based on platelet-copper
  • surface-modified metal effect pigments comprise at least one dielectric layer, optionally at least one protective layer, as well as a surface modification with at least one epoxide group-containing compound.
  • the present invention comprises the use of surface-modified metal effect pigments in one
  • the platelet-shaped copper-based surface-modified metal effect pigments comprise at least one dielectric layer, optionally at least one protective layer, as well as a surface modification with at least one epoxide group-containing compound having at least two epoxide groups.
  • the present invention comprises the use of surface-modified metal effect pigments in one
  • the present invention comprises a powder-coated article comprising a powdered lacquer comprising surface-modified effect pigments having a specific epoxide equivalent weight in the range from 119,000 to 800.
  • the present invention comprises surface-modified effect pigments based on a platelet-shaped substrate which is coated with at least one dielectric layer, optionally at least one protective layer, and a surface modification with at least one epoxide group-containing compound having an epoxide equivalent weight in the range from 10 to 20,000 ,
  • the present invention comprises surface-modified pearlescent pigments based on natural or synthetic mica, which is coated with at least one dielectric layer, optionally at least one protective layer, and a surface modification with at least one epoxide group-containing compound having an epoxide equivalent weight in the range from 10 to 20,000.
  • the present invention comprises surface-modified metallic effect pigments based on platelet-shaped aluminum, which is coated with at least one dielectric layer, optionally at least one protective layer, and with surface modification with at least one epoxide group-containing compound having an epoxide equivalent weight in the range from 10 to 20,000.
  • the described surface-modified effect pigments are particularly suitable for the pigmentation of powder coatings, which are produced by the dry blend process.
  • the segregation of effect pigment and powder coating, which is frequently observed here during application, can be largely avoided by using the surface-modified effect pigments described.
  • the surface-modified effect pigments to be used according to the invention are mixed with a powder coating by the dry blend method and then applied by the corona method, it is possible to almost completely prevent adhesion of the effect pigments to the electrode (s) and impact plate of the powder coating gun. In particular, there is practically no adhesion at least over a period of 20 s at 100 kV and 100 ⁇ application voltage.
  • black spots by the use of the invention to be used
  • surface-modified effect pigments are also used in powder coatings which are produced by the bonding process.
  • Powder coatings which contain the surface-modified effect pigments to be used according to the invention are distinguished by the fact that they lead to a good coating of the edges in the baked state after the coating process. An edge escape can thus not be observed.
  • Surface-modified effect pigments to be used according to the invention are present at 10% by weight, preferably in a range from 0.5 to ⁇ 8.0% by weight, more preferably in a range from 0.7 to ⁇ 6% by weight and very particularly preferably in a range from 1, 0 to -5 wt .-%, each based on the total weight of the pigmented powder coating.
  • inventive powder finishes can additionally be any material.
  • Charge control additives and / or trickle agents e.g. pyrolytically produced alumina or pyrolytically produced silicon dioxide are added. These can positively influence the flow behavior of the powder paint.
  • Powder coatings containing surface-modified effect pigments may be suitable not only indoors but also for outdoor applications.
  • Surface-modified effect pigments used in powder coatings for outdoor use should contain a weather-stabilized effect pigment precursor such as the commercially available Phoenix XT series, the Phoenix CFE series, the Symic OEM series or even the LUXAN CFX series from Eckart GmbH.
  • the weather-stable effect pigment precursors can be prepared, for example, analogously to EP 1 682 622 B1 and are distinguished by excellent UV and weather stability.
  • Facade cleaning ability for example, a hand cleaning method can be used.
  • Powder coatings containing the surface-modified effect pigments to be used according to the invention are distinguished by improved cleanability compared to the corresponding ones
  • the surface-modified effect pigments can also be used in other solvent-free coating compositions, in particular in toners.
  • the invention thus also relates to toners which contain the surface-modified effect pigments.
  • the invention also includes articles which are printed with a toner containing the surface-modified effect pigments.
  • Articles printed with the toner according to the invention are, for example, printed paper, cardboard or films.
  • the present invention relates to the use of surface-modified effect pigments in toners, wherein the surface-modified effect pigments based on a platelet-shaped substrate comprise a dielectric layer, optionally at least one
  • Protective layer as well as a surface modification with at least one epoxide group-containing compound.
  • the present invention relates to the use of surface-modified effect pigments in toners, wherein the surface-modified effect pigments based on a platelet-shaped substrate comprise a dielectric layer, optionally at least one
  • Protective layer as well as a surface modification with at least one epoxide group-containing compound having at least two epoxy groups.
  • the present invention relates to a toner containing surface-modified effect pigments, wherein the surface-modified effect pigments based on a platelet-shaped substrate comprise a dielectric layer, optionally at least one
  • the present invention relates to a toner containing surface-modified effect pigments, wherein the surface-modified effect pigments based on a platelet-shaped substrate comprise a dielectric layer, optionally at least one
  • Protective layer as well as a surface modification with at least one epoxide group-containing compound having at least two epoxy groups.
  • the invention will be described in more detail by means of examples without wishing to be limited thereto.
  • the surface-modified effect pigments were used in various commercially available powder coatings.
  • Epoxidqäuivalentconstru 140 to 170 dissolved in 60 g of ethanol having an H 2 0 content of 35 wt .-% and then mixed with the pigment in the kneader. After a mixing time of 20 minutes, the mixture was dried at 100.degree. The resulting surface-modified effect pigment with a
  • Boiling temperature brought. With stirring, initially 2.0 g of H 2 O and then within one hour a solution of 2.17 g of Ce (NO 3 ) 3 in 100 g of isopropanol was added. Subsequently, a solution of 0.45 g
  • the pigment filter cake was submitted in a laboratory kneader Fa. IKA.
  • 2.5 g of epoxy group-containing compound (Cyracure 6107, Dow Corning, epoxide equivalent weight 131 to 140) in 30 g
  • the pigment filter cake was dried at 120 ° C in a vacuum oven.
  • the resulting effect pigment served as a comparison material for the subsequent powder paint applications.
  • the pigment filter cake was dried at 120 ° C in a vacuum oven.
  • Standard aluminum powder PCU 3500 (Eckart GmbH): commercially available stabilized aluminum pigment.
  • the starting material is standard aluminum powder PCU 3500, a commercial! available stabilized aluminum pigment used (Eckart GmbH), wherein according to Example 1 of WO 2005/063897 A2, the further layer mitteis spray-drying was applied.
  • the standard aluminum powder PCR 501 used there instead of the standard aluminum powder PCR 501 used there, the type standard aluminum powder PCU 3500 was used.
  • the respective effect pigment was combined with the highly weather-resistant powder coating 059/82170 black (Tiger) and 0.2% Acematt OK 412 (Evonik) with ThermoMix for 4 minutes at level 4 incorporated.
  • the pigmentation level was 5.0 wt .-%, since in this pigmentation verifiable application behavior is achievable
  • the powder paint was weighed out to 95.0% by weight.
  • Total amount of powder paint in the mixer was 300 g plus 0.6 g Acematt OK 412.
  • ThermoMix is a commercial kitchen mixer (Vorwerk).
  • the additive Acematt OK 412 is SiO 2 particles having a mean agglomerate particle size of 6.0 ⁇ m, which in this application assumes the function of a pouring agent.
  • the Puiver! Acke were with the powder coating gun OptiSelect (ITWGema) in a commercial kitchen mixer (Vorwerk).
  • Black spots are areas on the powder coating surface that are caused by an inhomogeneous distribution of the effect pigments. Since these phenomena are in the macroscopic range, a lacquer-technically trained look is needed to assess the appearance. In particular, very smooth structures with a very smooth course without the appearance of black spots are preferred.
  • Example 40 kV-10 ⁇ / 2.5 Nm3 / h-70% 100 kV-100 ⁇ / 2.5 Nm3 / h-70% or pre-application runner Application Black Application Black
  • Example 5 buildup yes a orange peel
  • Comparative examples contained clearly black spots were to be recognized after the application, whereas in powder coatings, which
  • Powder coatings which contained surface-modified effect pigments according to the examples according to the invention had, compared with the corresponding powder paints with effect pigments For example, a significantly more uniform structure and a smoother course of the pigmented powder coating can be seen.
  • Comparative Example 6 was an effect pigment prepared according to WO 2005/063897 A2. Effect pigments prepared in this way can be applied very well in a powder paint application because of comparable electrostatic properties of the powder coating particles and the effect pigments coated with the corresponding binder. In contrast to powder application which contain the effect pigments to be used according to the invention, these powder coating applications are distinguished by their optical depth effect. An observer perceives a certain glittering effect over the entire viewing angle. A powder coating containing effect pigments according to Comparative Example 6 therefore has an overall more lively effect than the powder coating containing a uniform appearance containing the invention
  • Figure 1 shows a light micrograph (light microscope Axio Imager Z1m, Zeiss) of the effect pigment of Comparative Example 5.
  • Figure 2 shows a light micrograph (light microscope Axio Imager Z1m, Zeiss) of the effect pigment of Comparative Example 5.
  • Powder coatings containing effect pigments from Comparative Examples 1, 3 and 4 had a medium to strong loss of effect. On the corresponding paint panels a very clear discoloration in the direction of black (color of the powder coating used) was observed. These paint panels looked extremely uneven and visually very unattractive after the test.
  • Powder coatings containing surface-modified effect pigments according to the examples according to the invention also had an effect loss. This was less pronounced. There was only a slight discoloration towards black. The desired gloss effect (generated by the respective surface-modified
  • the specific epoxide equivalent weight is understood to mean the amount of pigment in grams which contains 16 grams of epoxide oxygen (epoxide oxygen).
  • the determination of the specific epoxide equivalent weight was carried out as follows:
  • 10.0 g not surface-modified effect pigment were weighed into a 80 ml beaker and in about 10 ml of chloroform and about 40 ml conc. Stirred up acetic acid. The sample was placed on a magnetic stirrer and immersed in a pH electrode. The sample was titrated with 0.1 N acetic perchloric acid. The consumption thus obtained is included as VB (2) in the calculation of the specific epoxide equivalent weight.
  • the weight in grams of the respective effect pigment depends on the expected specific epoxide equivalent weight and is equal to the determination of the zero value.
  • the respective weight can be
  • N normality of the titrant
  • epoxide equivalent weight is meant the amount of pigment in grams which contains 16 grams of epoxide oxygen (epoxide oxygen). The determination of the epoxide equivalent weight was carried out as follows:
  • the amounts of epoxide group-containing compound were weighed into a 80 ml beaker according to Table 3 and concentrated in about 10 ml of chloroform and about 40 mi. Acetic acid dissolved. Approximately 2.5 g of cetyltrimethylammonium bromide were added and dissolved with stirring, if appropriate also heating. The sample was placed on a magnetic stirrer and immersed in a pH electrode. The sample was titrated with 0.1 N acetic perchloric acid.
  • Epoxide equivalent weight Einwaa S e (g) ⁇
  • N normality of the titrant
  • nonmetallic piuschtchenförmigen substrates was determined using a device from. Maivern (device: MALVERN Mastersizer 2000) according to the manufacturer. For this purpose, about 0.1 g of the corresponding effect pigment as an aqueous suspension, without the addition of dispersing aid, with constant stirring by means of a Pasteur pipette in the sample preparation cell of the measuring device and measured several times. From the individual measurement results, the resulting averages were formed. The evaluation of the scattered light signals was carried out according to the Fraunhofer method.
  • the size distribution curve of the effect pigments based on metallic platelet-shaped substrates was measured with a Quantachrome device (device: Cilas 1064) according to the manufacturer's instructions. For this purpose, about 50 ml of the respective pigment were suspended in isopropanol, 300
  • the average diameter D50 is the Dso value of the cumulative frequency distribution of the volume components
  • the D 5 o value indicates that 50% of the effect pigments have a diameter which is equal to or less than the stated value, for example 20 ⁇ m. Accordingly, the Dgo value indicates that 90% of the effect pigments have a diameter equal to or less than the respective value. Furthermore, the Di 0 value indicates that 10% of the effect pigments have a diameter equal to or less than the respective values.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne l'utilisation de pigments à effet à surface modifiée, dans un agent de revêtement exempt de solvant, les pigments à effet à surface modifiée présentant un substrat en forme de plaquettes et au moins une couche diélectrique, au moins une couche protectrice optionnelle pouvant être appliquée sur au moins ladite couche diélectrique, et les pigments à effet étant modifiés sur leurs surfaces, par au moins un composé renfermant des groupes époxyde, sous réserve qu'au moins ledit composé renfermant les groupes époxyde ne contienne aucun atome de silicium. L'invention concerne en outre une laque en poudre qui renferme ces pigments à effet à surface modifiée, ainsi qu'un objet qui est revêtu d'une laque en poudre renfermant ces pigments à effet à surface modifiée.
PCT/EP2011/058593 2010-05-26 2011-05-25 Utilisation de pigments à effet à surface modifiée, dans un agent de revêtement exempt de solvant, agent de revêtement exempt de solvant et objet revêtu WO2011147892A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11724151.3A EP2576702A1 (fr) 2010-05-26 2011-05-25 Utilisation de pigments à effet à surface modifiée, dans un agent de revêtement exempt de solvant, agent de revêtement exempt de solvant et objet revêtu

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102010021530A DE102010021530A1 (de) 2010-05-26 2010-05-26 Verwendung oberflächenmodifizierter Effektpigmente in einem lösemittelfreien Beschichtungsmittel, lösemittelfreies Beschichtungsmittel und beschichteter Gegenstand
DE102010021530.9 2010-05-26

Publications (1)

Publication Number Publication Date
WO2011147892A1 true WO2011147892A1 (fr) 2011-12-01

Family

ID=44453885

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/058593 WO2011147892A1 (fr) 2010-05-26 2011-05-25 Utilisation de pigments à effet à surface modifiée, dans un agent de revêtement exempt de solvant, agent de revêtement exempt de solvant et objet revêtu

Country Status (3)

Country Link
EP (1) EP2576702A1 (fr)
DE (1) DE102010021530A1 (fr)
WO (1) WO2011147892A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10391043B2 (en) 2014-12-19 2019-08-27 Eckart Gmbh Effect pigments with high chroma and high brilliancy, method for the production and use thereof
US10759941B2 (en) 2014-12-19 2020-09-01 Eckart Gmbh Metal effect pigments with high chroma and high brilliancy, method for the production and use thereof
US10934436B2 (en) 2014-12-19 2021-03-02 Eckart Gmbh Effect pigments having high transparency, high chroma and high brilliancy, method for the production and use thereof
US10947391B2 (en) 2014-12-19 2021-03-16 Eckart Gmbh Gold-coloured effect pigments having high chroma and high brilliancy, method for the production and use thereof
US11202739B2 (en) 2014-12-19 2021-12-21 Eckart Gmbh Red-coloured decorative pigments with high chroma and high brilliancy, method for their production and use of same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019516672A (ja) 2016-04-15 2019-06-20 エッカルト ゲゼルシャフト ミット ベシュレンクテル ハフツングＥｃｋａｒｔ ＧｍｂＨ 表面変性エフェクト顔料およびネイルエナメル組成物
CN111225650A (zh) 2017-10-18 2020-06-02 埃卡特有限公司 含有压花效果颜料和表面改性压花效果颜料的指甲油组合物

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998046682A1 (fr) 1997-04-11 1998-10-22 Engelhard Corporation Composition d'enduction en poudre a pigment lamellaire et a resine
EP0764191B1 (fr) 1995-04-10 2001-11-07 MERCK PATENT GmbH pigment de type plaquette a surface traitee et leurs procedes de fabrication
EP1339806A2 (fr) 2000-06-20 2003-09-03 Engelhard Corporation Composition de revetement en poudre amelioree et procede
WO2005063897A2 (fr) 2003-12-23 2005-07-14 Eckart Gmbh & Co. Kg Pigments metalliques a revetement de liant reticulable, composition de revetement, procede de production desdits pigments metalliques a revetement et leur utilisation
US20050228078A1 (en) * 2004-04-07 2005-10-13 Yung Chi Paint & Varnish Mfg. Co., Ltd. Compositions and method for surface treatment of pigments
WO2006136435A2 (fr) 2005-06-24 2006-12-28 Eckart Gmbh Pigments nacres a revetement de liants reticulables, composition de revetement, procede de production des pigments nacres et leur utilisation
EP1646693B1 (fr) 2003-07-18 2007-01-24 Engelhard Corporation Precurseurs de revetement poudreux et leur utilisation dans des compositions de revetement poudreux
EP1682622B1 (fr) 2004-08-26 2007-08-22 Eckart GmbH & Co. KG PIGMENTS NACRES PRESENTANT UN REVETEMENT DE SiO2 ET D'OXYDE DE CERIUM
DE102006009131A1 (de) 2006-02-24 2007-09-06 Eckart Gmbh & Co.Kg Mit anorganisch/organischen Mischschichten beschichtete Perlglanzpigmente und Verfahren zu deren Herstellung
EP1812518B1 (fr) 2005-08-05 2008-02-13 Eckart GmbH Pigments a lustre nacre pourvus d'un revetement superficiel, leur procede de production, et leur utilisation
EP1980594B1 (fr) 2007-04-05 2009-06-03 Eckart GmbH Pigments à effet comprenant un substrat de type paillettes
EP2098574A2 (fr) 2008-03-03 2009-09-09 Xerox Corporation Pigment nacré ou métallique fonctionnalisé de greffe sur des polymères de polyester pour images d'effets spéciaux

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4321005A1 (de) * 1993-06-24 1995-01-05 Merck Patent Gmbh Perlglanzpigment für Wasserlacksysteme
DE19820112A1 (de) * 1998-05-06 1999-11-11 Eckart Standard Bronzepulver Mit reaktiven Orientierungshilfsmitteln beschichtete Effektpigmente
DE10054980C2 (de) * 2000-11-06 2003-02-06 Merck Patent Gmbh Stabilisierung von Perlglanzpigmenten

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0764191B1 (fr) 1995-04-10 2001-11-07 MERCK PATENT GmbH pigment de type plaquette a surface traitee et leurs procedes de fabrication
WO1998046682A1 (fr) 1997-04-11 1998-10-22 Engelhard Corporation Composition d'enduction en poudre a pigment lamellaire et a resine
EP1339806A2 (fr) 2000-06-20 2003-09-03 Engelhard Corporation Composition de revetement en poudre amelioree et procede
EP1339806B1 (fr) 2000-06-20 2005-10-19 Engelhard Corporation Composition de revetement en poudre amelioree et procede
EP1646693B1 (fr) 2003-07-18 2007-01-24 Engelhard Corporation Precurseurs de revetement poudreux et leur utilisation dans des compositions de revetement poudreux
WO2005063897A2 (fr) 2003-12-23 2005-07-14 Eckart Gmbh & Co. Kg Pigments metalliques a revetement de liant reticulable, composition de revetement, procede de production desdits pigments metalliques a revetement et leur utilisation
US20050228078A1 (en) * 2004-04-07 2005-10-13 Yung Chi Paint & Varnish Mfg. Co., Ltd. Compositions and method for surface treatment of pigments
US7618489B2 (en) 2004-04-07 2009-11-17 Yung Chi Paint & Varnish Mfg. Co., Ltd. Compositions and method for surface treatment of pigments
EP1682622B1 (fr) 2004-08-26 2007-08-22 Eckart GmbH & Co. KG PIGMENTS NACRES PRESENTANT UN REVETEMENT DE SiO2 ET D'OXYDE DE CERIUM
DE102005032346A1 (de) * 2005-06-24 2007-01-04 Eckart Gmbh & Co.Kg Perlglanzpigmente mit vernetzbarer Bindemittelbeschichtung, Beschichtungszusammensetzung, Verfahren zur Herstellung der beschichteten Perlglanzpigmente und deren Verwendung
WO2006136435A2 (fr) 2005-06-24 2006-12-28 Eckart Gmbh Pigments nacres a revetement de liants reticulables, composition de revetement, procede de production des pigments nacres et leur utilisation
EP1812518B1 (fr) 2005-08-05 2008-02-13 Eckart GmbH Pigments a lustre nacre pourvus d'un revetement superficiel, leur procede de production, et leur utilisation
DE102006009131A1 (de) 2006-02-24 2007-09-06 Eckart Gmbh & Co.Kg Mit anorganisch/organischen Mischschichten beschichtete Perlglanzpigmente und Verfahren zu deren Herstellung
EP1980594B1 (fr) 2007-04-05 2009-06-03 Eckart GmbH Pigments à effet comprenant un substrat de type paillettes
EP2098574A2 (fr) 2008-03-03 2009-09-09 Xerox Corporation Pigment nacré ou métallique fonctionnalisé de greffe sur des polymères de polyester pour images d'effets spéciaux

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HANS PFEIFER, JOURNAL FÜR OBERFLÄCHENTECHNIK, January 2003 (2003-01-01), pages 24 - 27

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10391043B2 (en) 2014-12-19 2019-08-27 Eckart Gmbh Effect pigments with high chroma and high brilliancy, method for the production and use thereof
US10759941B2 (en) 2014-12-19 2020-09-01 Eckart Gmbh Metal effect pigments with high chroma and high brilliancy, method for the production and use thereof
US10799432B2 (en) 2014-12-19 2020-10-13 Eckart Gmbh Effect pigments with high chroma and high brilliancy, method for the production and use thereof
US10934436B2 (en) 2014-12-19 2021-03-02 Eckart Gmbh Effect pigments having high transparency, high chroma and high brilliancy, method for the production and use thereof
US10947391B2 (en) 2014-12-19 2021-03-16 Eckart Gmbh Gold-coloured effect pigments having high chroma and high brilliancy, method for the production and use thereof
US11202739B2 (en) 2014-12-19 2021-12-21 Eckart Gmbh Red-coloured decorative pigments with high chroma and high brilliancy, method for their production and use of same

Also Published As

Publication number Publication date
DE102010021530A1 (de) 2011-12-01
EP2576702A1 (fr) 2013-04-10

Similar Documents

Publication Publication Date Title
WO2011147892A1 (fr) Utilisation de pigments à effet à surface modifiée, dans un agent de revêtement exempt de solvant, agent de revêtement exempt de solvant et objet revêtu
EP0837911B1 (fr) Pigment de dioxyde de titane sous forme de plaquettes
EP2691478B1 (fr) Pigments nacrés stables aux intempéries, procédé de fabrication correspondant et utilisation
EP3049483B1 (fr) Pigments à effet métallique modifiés comportant une couche de silane qui contient au moins deux silanes bifonctionnels différents
DE102012109407A1 (de) Wetterstabile Perlglanzpigmente, Verfahren zu ihrer Herstellung und Verwendung
EP2571943B1 (fr) Particules fonctionnalisées et leur utilisation
DE4323914A1 (de) Perlglanzpigment-Zubereitung
WO2009152907A1 (fr) Paillettes de vitrocéramique pour utilisation dans des pigments
EP2698403B1 (fr) Pigments nacrés modifiés en surface et leur utilisation dans les laques en poudre
DE102005032346A1 (de) Perlglanzpigmente mit vernetzbarer Bindemittelbeschichtung, Beschichtungszusammensetzung, Verfahren zur Herstellung der beschichteten Perlglanzpigmente und deren Verwendung
WO2004099319A2 (fr) Pigment d'interference a haut pouvoir couvrant
WO2014019639A1 (fr) Pigments à effet
DE102007061701A1 (de) Metalleffektpigmente, Verfahren zu deren Herstellung sowie Verwendung derselben und Pulverlack
EP3442491B1 (fr) Pigment a effet a surface modifie et composition de vernis a ongles
WO2003095564A1 (fr) Pigments brillants goniochromatiques
WO2021200135A9 (fr) Méthode de production de microparticules d'oxyde de titane revêtues de zircone, microparticules d'oxyde de titane revêtues de zircone et utilisation associée
EP1716199A2 (fr) Procede de production de resines polyester a additifs nanoscalaires pour peinture pulverulente
EP3119840A1 (fr) Pigments à effet
KR20060052824A (ko) 분말 코팅 전구체 및 그의 분말 코팅 조성물에서의 용도
EP2616514A1 (fr) Granulés de pigments
EP2917286B1 (fr) Pigment à activité photocatalytique, son procédé de fabrication et moyen de revêtement
DE3503957C1 (de) Beschichtungsmittel fuer Entspiegelungsschichten und Verfahren zu seiner Herstellung
EP2983836B1 (fr) Procédé permettant de recouvrir d'une laque en poudre un objet en matière plastique ou en verre
DE102009023158A1 (de) Beschichtete Partikel und deren Verwendung
DE102013017267A1 (de) Verfahren zum Pulverlackieren eines Glasgegenstandes

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11724151

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

REEP Request for entry into the european phase

Ref document number: 2011724151

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2011724151

Country of ref document: EP