WO2006021301A1 - Powdery pigment preparations for the hue range from red to orange - Google Patents

Powdery pigment preparations for the hue range from red to orange Download PDF

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Publication number
WO2006021301A1
WO2006021301A1 PCT/EP2005/008410 EP2005008410W WO2006021301A1 WO 2006021301 A1 WO2006021301 A1 WO 2006021301A1 EP 2005008410 W EP2005008410 W EP 2005008410W WO 2006021301 A1 WO2006021301 A1 WO 2006021301A1
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WO
WIPO (PCT)
Prior art keywords
pigment
pigments
weight
red
orange
Prior art date
Application number
PCT/EP2005/008410
Other languages
German (de)
French (fr)
Inventor
Mikael Johansson
Oliver Seeger
Ruth Genuneit
Sonja Borgmann
Kirill Bramnik
Original Assignee
Basf Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO2006021301A1 publication Critical patent/WO2006021301A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0002—Grinding; Milling with solid grinding or milling assistants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0092—Dyes in solid form
    • 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
    • C09C1/0081—Composite particulate pigments or fillers, i.e. containing at least two solid phases, except those consisting of coated particles of one compound
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • C01P2006/66—Hue (H*)

Definitions

  • Powdered Pigmentzurunge ⁇ for the hue range from red to orange
  • the present invention relates to pulverulent pigment preparations for the color tone range from red to orange, corresponding to a CIELAB color angle h of from -20 to 60 °, which are used as essential components,
  • the invention relates to a process for the preparation of these Pigmentzuberei ⁇ lines and their use for coloring paints, printing inks, plastics, building materials and preparations of decorative cosmetics.
  • Pigment preparations containing both organic and inorganic pigment have been of particular interest for a long time since they offer the possibility of exploiting the advantages of organic pigments (high color strength, high color purity) with those of inorganic pigments (good hiding power, high gloss). to combine.
  • Such pigment preparations have hitherto been commercially available only on the basis of highly brilliant bismuth vanadate (CI Pigment Yellow 184) as an inorganic pigment. These pigment preparations can therefore meet the requirements in terms of coloristic and durability. For the color range red to orange (- 20 ° ⁇ h ⁇ 60 °), however, there are no satisfactory cheaper alternatives available.
  • US Pat. No. 4,226,634 relates to the common wet milling of nickel titanium and nickel chrome yellow with organic yellow pigments or perylene-based red pigments with glass beads under the action of shearing forces. It should be noted that the dry grinding of mixtures of these pigments gives coatings with significantly worse gloss and hiding power.
  • US Pat. No. 4,222,788 discloses a process for the preparation of mixtures of nickel titanium and nickel chrome yellow with organic azo pigments, in which the inorganic pigment is already added in the synthesis of the organic pigment. It is also noted herein that dry blending of the final pigments results in pigment formulations that give finishes with inferior gloss.
  • EP-A-816 440 describes bismuth vanadate-based yellow to reddish yellow pigment powder mixtures which are obtained by dry grinding of bismuth vanadate with the organic pigment.
  • EP-A-985 712 discloses yellow to reddish-yellow pigment preparations in granulate form based on bismuth vanadate or rutile mixed-phase pigments, which are obtained by aqueous milling of inorganic and organic pigment with glass beads and subsequent spray-drying.
  • the invention had the object of providing pigment preparations for the Farbtonbe ⁇ rich red to orange, which have a higher color strength and thus yield compared to a classic blend of the individual present in paste form dispersed pigments.
  • pigment preparations have been found for the hue range from red to orange, corresponding to a CIELAB color angle h of -20 to 60 °, which are essential components
  • the pigment preparations according to the invention are distinguished, in particular, by their high color strength, which is up to 35% higher in varnish than in the individual rubs of the pigments, and in the gloss of their varnishes.
  • the high color strength is essentially due to the fineness of the organic pigment (A), which is achieved by intensive mixing with the hard inorganic pigment (B) acting as a grinding body.
  • the mean particle size of the organic pigments (A) used before mixing is generally about 700 nm and after Mi ⁇ at ⁇ 500 nm, in particular at ⁇ 300 nm.
  • the pigment formulations according to the invention despite the finely divided organic pigment (A), show essentially unchanged weather fastness and chemical resistance, since the particle size of the organic pigment is expected to deteriorate as the particle size decreases would have been.
  • the inorganic pigment contained as component (B) in the pigment preparations according to the invention has a Mohs hardness> 5, preferably> 6.
  • component (B) Particularly suitable as component (B) are inorganic pigments from the group of rutile and rutile mixed phase pigments, the rutile mixed phase pigments being preferred.
  • pigments can be used. Examples include rutile pigments doped with chromophoric ions of the metals nickel, chromium, manganese, iron and / or niobium.
  • the hue of the inorganic pigments (B) is at least in the vicinity of the desired color range for the pigment preparation. It is therefore mainly yellow or brown pigments are used.
  • particularly suitable pigments (B) are Cl. Pigment Yellow 53, 157, 158, 159, 160, 161, 162, 163, 164 and 189 and Cl. Pigment Brown 24 and 33 as well as Cl. Pigment White 6. Particular preference is given here to Cl. Pigment Brown 24 and also Cl. Pigment Yellow 42.
  • the organic pigment contained as component (A) in the pigment preparations of the invention is a pyrazolone quinazolone pigment, an isoindoline pigment, an azo pigment, a diketopyrrolopyrrole pigment or a quinophthalone pigment.
  • organic pigments (A) may be included.
  • Their color shade is preferably at least in the vicinity of the color tone range desired for the pigment preparation, so that in particular red, orange and yellow pigments are used, the yellow pigments preferably being combined with red or orange pigments.
  • Isoindoline pigments Cl. Pigment Yellow 139 and 185; Cl. Pigment Orange 61 and 69;
  • Diketopyrrolopyrrole pigments Cl. Pigment Orange 71 and 73;
  • Quinophthalone pigments Cl. Pigment Yellow 138.
  • the or ⁇ ganische pigment forming the component (A) of the pigment preparations according to invention lies in finely divided form in the pigment preparations according to invention. It usually has mean particle sizes ⁇ 500 nm, preferably ⁇ 300 nm.
  • the pigment preparations according to the invention contain from 20 to 99% by weight, in particular from 30 to 70% by weight, of the organic component (A) and from 1 to 80% by weight, especially from 30 to 70% by weight, of the inorganic Component (B).
  • the pigment preparations according to the invention are advantageously obtainable by the likewise inventive production process in which organic pigment (A) and inorganic pigment (B) are mixed intensively dry.
  • the inorganic pigment (B) acts as a grinding medium for the organic pigment (A) and thus causes a comminution of the organic pigment particles.
  • Techniques suitable for carrying out the process according to the invention are those in which organic and inorganic pigments are mixed so intensively that the hard inorganic pigment (B) can act as a grinding medium for the organic pigment (A).
  • This shear mixing may be e.g. in mixers such as Lödige mixers, Eirich mixers and Ruberg mixers.
  • the grinding action of the inorganic pigment (B) can be further enhanced by the fact that the mixing apparatus has further internals, e.g. with high circumferential speed rotating cutter heads, which increase the effect on the organic pigment (A) shear forces.
  • the above mixers may e.g. be equipped with such cutter heads.
  • the grinding effect of the inorganic pigment is also enhanced in apparatuses which cause additional shear by using heavy weights.
  • a special a suitable example for this is a Koller.
  • the slowly rotating Koller ⁇ stones a strong mechanical contact pressure is generated, which promotes the grinding action of the inorganic pigment.
  • Usual mixing times are e.g. when using a Lödige mixer at 5 to 60 minutes and when using a Koller at 0.5 to 10 hours.
  • the pigment preparations according to the invention are outstandingly suitable for coloring paints, printing inks, plastics, building materials and preparations of decorative cosmetics. They are characterized by their advantageous coloristic properties, in particular their high color strength and gloss, and their high durability, especially weather fastness and chemical resistance.
  • X- 1 parts by weight of organic pigment (A) and Y 1 part by weight of inorganic pigment (B) were mixed for 15 minutes in a Lödige mixer without rotating cutter heads.
  • a mixture of 50 g of the respective pigment preparation and 200 g of alkyd melamine stoving lacquer (45% by weight solids) was shaken with 300 g glass beads (3 mm diameter) for 90 minutes with a Skandex instrument, then on aluminum Q panels applied blanket (Filmauszieh réelle type 238 II, Fa. Erichsen) and baked at 130 0 C for 30 min.
  • the color angle h was determined using a spectrophotometer Spectrolino (Gretag-Macbeth).
  • Pigment Orange 67 58.5 parts by weight of Cl.
  • Pigment Brown 24 Standard Red 63 parts by weight Cl.
  • Pigment Brown 24 1 part by weight of Cl.
  • Pigment Yellow 42
  • FAE value has been assigned 100 (default).
  • FAE values ⁇ 100 mean a higher color strength than the standard, FAE value> 100 correspondingly a smaller color intensity.
  • the painted sheets were loaded for 2000 hours in a Xenotest 1200 (device from Heraeus) in accordance with EN ISO 4892-2.
  • the color change of the weathered sheets was then assessed according to the gray scale according to ISO 105-A02. This scale ranges from grade 5 (unchanged finish) to grade 1 (heavily modified finish).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Composite Materials (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The invention relates to powdery pigment preparations for the hue range from red to orange, corresponding to a CIELAB hue angle h of -20 to 60°, which comprise, as the essential components, (A) 20 to 99 % by weight of at least one finely divided organic pigment, selected from the group of pyrazolone quinazolone pigments, isoindoline pigments, azo pigments, diketopyrrolopyrrole pigments and quinophthalone pigments, and (B) 1 to 80 % by weight of at least one inorganic pigment having a Mohs' hardness of = 5, and which are obtained by intensively mixing the dry components (A) and (B).

Description

Pulverförmige Pigmentzubereitungeπ für den Farbtonbereich von Rot bis OrangePowdered Pigmentzubereitungeπ for the hue range from red to orange
Beschreibungdescription
Die vorliegende Erfindung betrifft pulverförmige Pigmentzubereitungen für den Farb¬ tonbereich von Rot bis Orange, entsprechend einem CIELAB Farbwinkel h von - 20 bis 60°, die als wesentliche Komponenten ,The present invention relates to pulverulent pigment preparations for the color tone range from red to orange, corresponding to a CIELAB color angle h of from -20 to 60 °, which are used as essential components,
(A) 20 bis 99 Gew.-% mindestens eines feinteiligen organischen Pigments, ausge- wählt aus der Gruppe der Pyrazolonchinazolonpigmente, Isoindolinpigmente,(A) 20 to 99% by weight of at least one finely divided organic pigment selected from the group of the pyrazolone quinazolone pigments, isoindoline pigments,
Azopigmente, Diketopyrrolopyrrolpigmente und Chinophthalonpigmente,Azo pigments, diketopyrrolopyrrole pigments and quinophthalone pigments,
undand
(B) 1 bis 80 Gew.-% mindestens eines anorganischen Pigments mit einer Mohs- schen Härte > 5(B) 1 to 80 wt .-% of at least one inorganic pigment having a Mohs hardness> 5
enthalten und durch intensives trockenes Mischen der Pigmente (A) und (B) erhältlich sind.and obtainable by intensive dry mixing of the pigments (A) and (B).
Außerdem betrifft die Erfindung ein Verfahren zur Herstellung dieser Pigmentzuberei¬ tungen sowie ihre Verwendung zur Einfärbung von Lacken, Druckfarben, Kunststoffen, Baustoffen und Zubereitungen der dekorativen Kosmetik.In addition, the invention relates to a process for the preparation of these Pigmentzuberei¬ lines and their use for coloring paints, printing inks, plastics, building materials and preparations of decorative cosmetics.
Pigmentzubereitungen, die sowohl organisches als auch anorganisches Pigment ent¬ halten, sind bereits seit längerer Zeit von besonderem Interesse, da sie die Möglichkeit bieten, die Vorteile organischer Pigmente (hohe Farbstärke, hohe Farbtonreinheit) mit denen anorganischer Pigmente (gutes Deckvermögen, hoher Glanz) zu kombinieren. Kommerziell erhältlich sind derartige Pigmentzubereitungen bislang lediglich auf Basis von hochbrillantem Bismutvanadat (Cl. Pigment Yellow 184) als anorganischem Pig¬ ment. Diese Pigmentzubereitungen können daher die Anforderungen im Hinblick auf Koloristik und Beständigkeit erfüllen. Für den Farbtonbereich Rot bis Orange (- 20° < h < 60°) stehen jedoch keine zufriedenstellenden billigeren Alternativen zur Verfügung.Pigment preparations containing both organic and inorganic pigment have been of particular interest for a long time since they offer the possibility of exploiting the advantages of organic pigments (high color strength, high color purity) with those of inorganic pigments (good hiding power, high gloss). to combine. Such pigment preparations have hitherto been commercially available only on the basis of highly brilliant bismuth vanadate (CI Pigment Yellow 184) as an inorganic pigment. These pigment preparations can therefore meet the requirements in terms of coloristic and durability. For the color range red to orange (- 20 ° <h <60 °), however, there are no satisfactory cheaper alternatives available.
In der Patentliteratur sind verschiedene Verfahren zur Herstellung von Mischungen organischer und anorganischer Pigmente beschrieben.The patent literature describes various processes for the preparation of mixtures of organic and inorganic pigments.
Das US-Patent 4 226 634 betrifft die gemeinsame Naßmahlung von Nickeltitan- und Nickelchromgelb mit organischen Gelbpigmenten bzw. Rotpigmenten auf Perylenbasis mit Glasperlen unter Einwirkung von Scherkräften. Es wird darauf hingewiesen, daß die trockene Mahlung von Gemischen dieser Pigmente Lackierungen mit deutlich schlechterem Glanz und schlechterem Deckvermögen ergibt. Aus dem US-Patent 4 222 788 ist ein Verfahren zur Herstellung von Mischungen von Nickeltitan- und Nickelchromgelb mit organischen Azopigmenten bekannt, bei dem das anorganische Pigment bereits bei der Synthese des organischen Pigments zugesetzt wird. Hier wird ebenfalls festgestellt, daß trockenes Mischen der fertigen Pigmente zu Pigmentzubereitungen führt, die Lackierungen mit schlechterem Glanz ergeben.US Pat. No. 4,226,634 relates to the common wet milling of nickel titanium and nickel chrome yellow with organic yellow pigments or perylene-based red pigments with glass beads under the action of shearing forces. It should be noted that the dry grinding of mixtures of these pigments gives coatings with significantly worse gloss and hiding power. US Pat. No. 4,222,788 discloses a process for the preparation of mixtures of nickel titanium and nickel chrome yellow with organic azo pigments, in which the inorganic pigment is already added in the synthesis of the organic pigment. It is also noted herein that dry blending of the final pigments results in pigment formulations that give finishes with inferior gloss.
Die EP-A-816 440 beschreibt auf Bismutvanadat basierende, gelbe bis rotstichtig gelbe Pigmentpulvergemische, die durch trockenes Mahlen von Bismutvanadat mit dem or¬ ganischen Pigment erhalten werden.EP-A-816 440 describes bismuth vanadate-based yellow to reddish yellow pigment powder mixtures which are obtained by dry grinding of bismuth vanadate with the organic pigment.
Schließlich sind aus der EP-A-985 712 gelbe bis rotstichig gelbe, auf Bismutvanadat- oder Rutilmischphasenpigmenten basierende Pigmentzubereitungen in Granulatform bekannt, die durch wäßrige Mahlung von anorganischem und organischem Pigment mit Glasperlen und anschließende Sprühtrocknung erhalten werden.Finally, EP-A-985 712 discloses yellow to reddish-yellow pigment preparations in granulate form based on bismuth vanadate or rutile mixed-phase pigments, which are obtained by aqueous milling of inorganic and organic pigment with glass beads and subsequent spray-drying.
Der Erfindung lag die Aufgabe zugrunde, Pigmentzubereitungen für den Farbtonbe¬ reich Rot bis Orange bereitzustellen, die gegenüber einer klassischen Abmischung der einzelnen, in Pastenform vorliegenden dispergierten Pigmente eine höhere Farbstärke und damit Ergiebigkeit aufweisen.The invention had the object of providing pigment preparations for the Farbtonbe¬ rich red to orange, which have a higher color strength and thus yield compared to a classic blend of the individual present in paste form dispersed pigments.
Demgemäß wurden Pigmentzubereitungen für den Farbtonbereich von Rot bis Orange, entsprechend einem CIELAB Farbwinkel h von - 20 bis 60°, gefunden, die als wesentli¬ che KomponentenAccordingly, pigment preparations have been found for the hue range from red to orange, corresponding to a CIELAB color angle h of -20 to 60 °, which are essential components
(A) 20 bis 99 Gew.-% mindestens eines feinteiligen organischen Pigments, ausge¬ wählt aus der Gruppe der Pyrazolonchinazolonpigmente, Isoindolinpigmente, Azopigmente, Diketopyrrolopyrrolpigmente und Chinophthalonpigmente,(A) 20 to 99% by weight of at least one finely divided organic pigment selected from the group of pyrazolone quinazolone pigments, isoindoline pigments, azo pigments, diketopyrrolopyrrole pigments and quinophthalone pigments,
undand
(B) 1 bis 80 Gew.-% mindestens eines anorganischen Pigments mit einer Mohs- schen Härte > 5(B) 1 to 80 wt .-% of at least one inorganic pigment having a Mohs hardness> 5
enthalten und durch intensives trockenes Mischen der Pigmente (A) und (B) erhältlich sind.and obtainable by intensive dry mixing of the pigments (A) and (B).
Weiterhin wurde ein Verfahren zur Herstellung dieser Pigmentzubereitungen gefunden, welches dadurch gekennzeichnet ist, daß man organisches Pigment (A) und anorgani¬ sches Pigment (B) intensiv trocken mischt. Außerdem wurde die Verwendung der Pigmentzubereitungen zur Einfärbung von La¬ cken, Druckfarben, Kunststoffen, Baustoffen und Zubereitungen der dekorativen Kos¬ metik gefunden.Furthermore, a process for the preparation of these pigment preparations was found, which is characterized in that one mixes dry organic pigment (A) and anorgani¬ cal pigment (B). In addition, the use of the pigment preparations for coloring patches, printing inks, plastics, building materials and preparations of decorative cosmetics has been found.
Die erfindungsgemäßen Pigmentzubereitungen zeichnen sich insbesondere durch ihre hohe Farbstärke, die in Lack bis zu 35% höher ist als die der Einzelanreibungen der Pigmente, sowie den Glanz ihrer Lackierungen aus. Die hohe Farbstärke ist im wesent¬ lichen auf die Feinteiligkeit des organischen Pigments (A) zurückzuführen, die durch das intensive Mischen mit dem als Mahlkörper wirkenden harten anorganischen Pig- ment (B) erzielt wird. So liegt die mittlere Teilchengröße der verwendeten organischen Pigmente (A) vor dem Mischen im allgemeinen bei etwa 700 nm und nach dem Mi¬ schen bei < 500 nm, insbesondere bei < 300 nm.The pigment preparations according to the invention are distinguished, in particular, by their high color strength, which is up to 35% higher in varnish than in the individual rubs of the pigments, and in the gloss of their varnishes. The high color strength is essentially due to the fineness of the organic pigment (A), which is achieved by intensive mixing with the hard inorganic pigment (B) acting as a grinding body. Thus, the mean particle size of the organic pigments (A) used before mixing is generally about 700 nm and after Mi¬ at <500 nm, in particular at <300 nm.
Dabei ist überraschend, daß dieser Effekt bei den erfindungsgemäßen Pigmentzube- reitungen beim trockenen Mischen und ohne Einsatz von Mahlkörpern oder weiteren Mahlhilfsmitteln erzielt wird. Das ist vor allem auch im Hinblick auf das US-Patent 4 226 634 überraschend, das wiederholt darauf hinweist, daß nur durch Naßmahlung unter Einsatz von Glasperlen hohe Farbstärken und hoher Glanz zu erreichen sind.It is surprising that this effect is achieved in the pigment preparations according to the invention during dry mixing and without the use of grinding media or other grinding auxiliaries. This is particularly surprising in view of the US Patent 4,226,634, which repeatedly indicates that only by wet grinding using glass beads high color strengths and high gloss can be achieved.
Insbesondere überraschend ist zudem, daß die erfindungsgemäßen Pigmentzuberei¬ tungen trotz der Feinteiligkeit des enthaltenen organischen Pigments (A) im wesentli¬ chen unveränderte Wetterechtheit und Chemikalienbeständigkeit zeigen, da mit zu¬ nehmender Verkleinerung der Teilchengröße des organischen Pigments eine Ver¬ schlechterung dieser Eigenschaften zu erwarten gewesen wäre.In addition, it is particularly surprising that the pigment formulations according to the invention, despite the finely divided organic pigment (A), show essentially unchanged weather fastness and chemical resistance, since the particle size of the organic pigment is expected to deteriorate as the particle size decreases would have been.
Das in den erfindungsgemäßen Pigmentzubereitungen als Komponente (B) enthaltene anorganische Pigment weist eine Mohs'sche Härte > 5, vorzugsweise > 6, auf.The inorganic pigment contained as component (B) in the pigment preparations according to the invention has a Mohs hardness> 5, preferably> 6.
Insbesondere als Komponente (B) geeignet sind anorganische Pigmente aus der Gruppe Rutil und Rutilmischphasenpigmente, wobei die Rutilmischphasenpigmente bevorzugt sind.Particularly suitable as component (B) are inorganic pigments from the group of rutile and rutile mixed phase pigments, the rutile mixed phase pigments being preferred.
Es können alle bekannten Pigmente zum Einsatz kommen. Beispielhaft aufgeführt sei¬ en mit farbgebenden Ionen der Metalle Nickel, Chrom, Mangan, Eisen und/oder Niob dotierte Rutilpigmente.All known pigments can be used. Examples include rutile pigments doped with chromophoric ions of the metals nickel, chromium, manganese, iron and / or niobium.
Selbstverständlich können verschiedene anorganische Pigmente (B) enthalten sein.Of course, various inorganic pigments (B) may be included.
Bevorzugt liegt der Farbton der anorganischen Pigmente (B) zumindest in der Nähe des für die Pigmentzubereitung gewünschten Farbtonbereichs. Es werden also vor allem Gelb- oder Braunpigmente verwendet. - Im einzelnen als besonders geeignete Pigmente (B) genannt seien Cl. Pigment Yellow 53, 157, 158, 159, 160, 161, 162, 163, 164 und 189 sowie Cl. Pigment Brown 24 und 33 sowie auch Cl. Pigment White 6. Bevorzugt sind dabei insbesondere Cl. Pigment Brown 24 und daneben auch Cl. Pigment Yellow 42.Preferably, the hue of the inorganic pigments (B) is at least in the vicinity of the desired color range for the pigment preparation. It is therefore mainly yellow or brown pigments are used. - Specifically mentioned as particularly suitable pigments (B) are Cl. Pigment Yellow 53, 157, 158, 159, 160, 161, 162, 163, 164 and 189 and Cl. Pigment Brown 24 and 33 as well as Cl. Pigment White 6. Particular preference is given here to Cl. Pigment Brown 24 and also Cl. Pigment Yellow 42.
Bei dem in den erfindungsgemäßen Pigmentzubereitungen als Komponente (A) enthal¬ tenen organischen Pigment handelt es sich um ein Pyrazolonchinazolonpigment, ein Isoindolinpigment, ein Azopigment, ein Diketopyrrolopyrrolpigment oder ein Chino- phthalonpigment.The organic pigment contained as component (A) in the pigment preparations of the invention is a pyrazolone quinazolone pigment, an isoindoline pigment, an azo pigment, a diketopyrrolopyrrole pigment or a quinophthalone pigment.
Selbstverständlich können auch verschiedene organische Pigmente (A) enthalten sein.Of course, various organic pigments (A) may be included.
Auch ihr Farbton liegt vorzugsweise zumindest in der Nähe des für die Pigmentzuberei¬ tung gewünschten Farbtonbereichs, so daß insbesondere Rot-, Orange- und Gelbpig- mente verwendet werden, wobei die Gelbpigmente bevorzugt mit Rot- oder Orange¬ pigmenten kombiniert werden.Their color shade is preferably at least in the vicinity of the color tone range desired for the pigment preparation, so that in particular red, orange and yellow pigments are used, the yellow pigments preferably being combined with red or orange pigments.
Als besonders geeignete Beispiele für die einzelnen Pigmentklassen seien genannt:Particularly suitable examples of the individual pigment classes are:
- Pyrazolonchinazolonpigmente:- Pyrazolonequinazolone pigments:
Cl. Pigment Orange 67 und Cl. Pigment Red 216;Cl. Pigment Orange 67 and Cl. Pigment Red 216;
Isoindolinpigmente: Cl. Pigment Yellow 139 und 185; Cl. Pigment Orange 61 und 69;Isoindoline pigments: Cl. Pigment Yellow 139 and 185; Cl. Pigment Orange 61 and 69;
Cl. Pigment Red 260;Cl. Pigment Red 260;
Azopigmente:azo pigments:
Cl. Pigment Yellow 2, 13, 62, 74, 151, 168 und 191 ; Cl. Pigment Orange 5, 13, 34, 36, 64 und 67;Cl. Pigment Yellow 2, 13, 62, 74, 151, 168 and 191; Cl. Pigment Orange 5, 13, 34, 36, 64 and 67;
Cl. Pigment Red 1, 2, 3, 4, 5, 23, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 51:1,51 :1 , 53, 53:1 , 57:1 , 58:2, 58:4, 112, 144, 146, 148, 166, 170, 184, 214, 220, 221 und 251.Cl. Pigment Red 1, 2, 3, 4, 5, 23, 48: 1, 48: 2, 48: 3, 48: 4, 49, 49: 1, 51: 1.51: 1, 53, 53: 1, 57: 1, 58: 2, 58: 4, 112, 144, 146, 148, 166, 170, 184, 214, 220, 221 and 251.
Diketopyrrolopyrrolpigmente: Cl. Pigment Orange 71 und 73;Diketopyrrolopyrrole pigments: Cl. Pigment Orange 71 and 73;
Cl. Pigment Red 254, 264 und 272;Cl. Pigment Red 254, 264 and 272;
Chinophthalonpigmente: Cl. Pigment Yellow 138.Quinophthalone pigments: Cl. Pigment Yellow 138.
Bevorzugt sind dabei insbesondere Cl. Pigment Yellow 139, Cl. Pigment Orange 67 und Cl. Pigment Red 170. Das die Komponente (A) der erfindungsgemäßen Pigmentzubereitungen bildende or¬ ganische Pigment liegt in den erfindungsgemäßen Pigmentzubereitungen in feinteiliger Form vor. Üblicherweise weist es mittlere Teilchengrößen < 500 nm, vorzugsweise < 300 nm, auf.Particularly preferred are Cl. Pigment Yellow 139, Cl. Pigment Orange 67 and Cl. Pigment Red 170. The or¬ ganische pigment forming the component (A) of the pigment preparations according to invention lies in finely divided form in the pigment preparations according to invention. It usually has mean particle sizes <500 nm, preferably <300 nm.
Die erfindungsgemäßen Pigmentzubereitungen enthalten 20 bis 99 Gew.-%, insbeson¬ dere 30 bis 70 Gew.-%, der organischen Komponente (A) und 1 bis 80 Gew.-%, vor allem 30 bis 70 Gew.-%, der anorganischen Komponente (B).The pigment preparations according to the invention contain from 20 to 99% by weight, in particular from 30 to 70% by weight, of the organic component (A) and from 1 to 80% by weight, especially from 30 to 70% by weight, of the inorganic Component (B).
Die erfindungsgemäßen Pigmentzubereitungen sind vorteilhaft nach dem ebenfalls erfindungsgemäßen Herstellungsverfahren zu erhalten, bei dem organisches Pigment (A) und anorganisches Pigment (B) intensiv trocken gemischt werden.The pigment preparations according to the invention are advantageously obtainable by the likewise inventive production process in which organic pigment (A) and inorganic pigment (B) are mixed intensively dry.
Das anorganische Pigment (B) wirkt hierbei als Mahlkörper für das organische Pigment (A) und bewirkt damit eine Zerkleinerung der organischen Pigmentteilchen.The inorganic pigment (B) acts as a grinding medium for the organic pigment (A) and thus causes a comminution of the organic pigment particles.
Beim erfindungsgemäßen Verfahren können sowohl die bei der Pigmentsynthese an¬ fallenden Rohpigmente als auch Pigmente, die bereits einem Pigmentfinish, d.h. einer Einstellung von Teilchenform und -große, unterzogen worden sind, eingesetzt werden.In the process according to the invention, it is possible to use both the crude pigments which are involved in the synthesis of the pigment and those which are already pigmented, i. a setting of particle shape and size, have been used.
Für das erfindungsgemäße Verfahren vorteilhaft ist, daß keine zusätzlichen Mahlkörper oder weiteren Mahlhilfsmittel verwendet und damit auch von der Pigmentzubereitung abgetrennt werden müssen. Weiterhin erübrigt sich auch ein Trocknungsschritt, da beim Mischen kein Lösungsmittel eingesetzt wird.It is advantageous for the process according to the invention that no additional grinding media or other grinding aids are used and therefore also have to be separated from the pigment preparation. Furthermore, a drying step is unnecessary since no solvent is used during mixing.
Zur Durchführung des erfindungsgemäßen Verfahrens eignen sich technische Appara¬ te, in denen organisches und anorganisches Pigment derart intensiv gemischt werden, daß das harte anorganische Pigment (B) als Mahlkörper für das organische Pigment (A) wirken kann.Techniques suitable for carrying out the process according to the invention are those in which organic and inorganic pigments are mixed so intensively that the hard inorganic pigment (B) can act as a grinding medium for the organic pigment (A).
Dieses Mischen unter Scherung kann z.B. in Mischern, wie Lödige-Mischern, Eirich- Mischem und Ruberg-Mischern, vorgenommen werden.This shear mixing may be e.g. in mixers such as Lödige mixers, Eirich mixers and Ruberg mixers.
Die Mahlwirkung des anorganischen Pigments (B) kann noch dadurch verstärkt wer¬ den, daß der Mischapparat weitere Einbauten, z.B. mit hoher Umfangsgeschwindigkeit rotierende Messerköpfe, aufweist, welche die auf das organische Pigment (A) wirken¬ den Scherkräfte erhöhen. Die obengenannten Mischer können z.B. mit derartigen Messerköpfen ausgerüstet werden.The grinding action of the inorganic pigment (B) can be further enhanced by the fact that the mixing apparatus has further internals, e.g. with high circumferential speed rotating cutter heads, which increase the effect on the organic pigment (A) shear forces. The above mixers may e.g. be equipped with such cutter heads.
Die mahlende Wirkung des anorganischen Pigments wird auch in Apparaten verstärkt, die durch Einsatz schwerer Gewichte eine zusätzliche Scherung bewirken. Ein beson- ders geeignetes Beispiel hierfür ist ein Koller. Durch die langsam rotierenden Koller¬ steine wird ein starker mechanischer Anpreßdruck erzeugt, der die Mahlwirkung des anorganischen Pigments fördert.The grinding effect of the inorganic pigment is also enhanced in apparatuses which cause additional shear by using heavy weights. A special a suitable example for this is a Koller. The slowly rotating Koller¬ stones a strong mechanical contact pressure is generated, which promotes the grinding action of the inorganic pigment.
Übliche Mischdauern liegen z.B. bei Verwendung eines Lödige-Mischers bei 5 bis 60 min und bei Verwendung eines Kollers bei 0,5 bis 10 h.Usual mixing times are e.g. when using a Lödige mixer at 5 to 60 minutes and when using a Koller at 0.5 to 10 hours.
Insbesondere bei Verwendung eines Kollers ist es zur Auflockerung von verbackenem Pigment empfehlenswert, an den Mischvorgang noch einen kurzen Mahlschritt anzu- schließen, z.B. einen Durchgang durch eine Stiftmühle, der in der Regel < 1 min dau¬ ert.In particular, when using a pug mill, it is advisable for loosening baked-on pigment to add a short milling step to the mixing process, e.g. a passage through a pin mill, which usually takes <1 min.
Die erfindungsgemäßen Pigmentzubereitungen sind hervorragend zur Einfärbung von Lacken, Druckfarben, Kunststoffen, Baustoffen und Zubereitungen der dekorativen Kosmetik geeignet. Sie zeichnen sich hierbei durch ihre vorteilhaften koloristischen Eigenschaften, insbesondere ihre hohe Farbstärke und ihren Glanz, und ihre hohe Be¬ ständigkeit, vor allem Wetterechtheit und Chemikalienbeständigkeit, aus.The pigment preparations according to the invention are outstandingly suitable for coloring paints, printing inks, plastics, building materials and preparations of decorative cosmetics. They are characterized by their advantageous coloristic properties, in particular their high color strength and gloss, and their high durability, especially weather fastness and chemical resistance.
BeispieleExamples
1) Herstellung von erfindungsgemäßen Pigmentzubereitungen1) Preparation of Pigment Preparations According to the Invention
Variante Ia:Variant Ia:
X1 Gew.-Teile organisches Pigment (A) und V1 Gew. -Teile anorganisches Pigment (B) wurden 15 min in einem Lödige-Mischer mit rotierenden Messerköpfen gemischt.X 1 part by weight of organic pigment (A) and V 1 part by weight of inorganic pigment (B) were mixed for 15 minutes in a Lödige mixer with rotating cutter heads.
Variante Ib:Variant Ib:
X-I Gew.-Teile organisches Pigment (A) und Y1 Gew.-Teile anorganisches Pigment (B) wurden 15 min in einem Lödige-Mischer ohne rotierende Messerköpfe gemischt.X- 1 parts by weight of organic pigment (A) and Y 1 part by weight of inorganic pigment (B) were mixed for 15 minutes in a Lödige mixer without rotating cutter heads.
Variante IIa:Variant IIa:
X1 Gew.-Teile organisches Pigment (A) und y-, Gew.-Teile anorganisches Pigment (B) wurden t, h in einem Koller verarbeitet. Das erhaltene Produkt wurde anschließend kurz (10 sec) in einer Stiftmühle (Abstand der Stifte 14,5 cm) gemahlen.X 1 part by weight of organic pigment (A) and y-, parts by weight of inorganic pigment (B) were processed in a Koller t, h. The resulting product was then ground briefly (10 sec) in a pin mill (pitch of pins 14.5 cm).
Variante IIb:Variant IIb:
X1 Gew.-Teile organisches Pigment (A) und Y1 Gew.-Teile anorganisches Pigment (B) wurden U h in einem Koller verarbeitet. Dann wurden weitere y2 Gew.-Teile anorgani- sches Pigment (B) zugegeben und weitere t2 h im Koller verarbeitet. Das erhaltene Produkt wurde anschließend kurz (10 sec) in einer Stiftmühle (Abstand der Stifte 14,5 cm) gemahlen.X 1 part by weight of organic pigment (A) and Y 1 part by weight of inorganic pigment (B) were processed U h in a Koller. Then, another y 2 parts by weight of inorganic added nice pigment (B) and processed further t 2 h in Koller. The resulting product was then ground briefly (10 sec) in a pin mill (pitch of pins 14.5 cm).
Weitere Einzelheiten zu diesen Versuchen sind in Tabelle 1 aufgeführt.Further details of these experiments are shown in Table 1.
Tabelle 1Table 1
Figure imgf000008_0001
2) Prüfung von erfindungsgemäßen Pigmentzubereitungen
Figure imgf000008_0001
2) Testing of Pigment Preparations According to the Invention
Die Beurteilung der koloristischen Eigenschaften erfolgte an Lackierungen, die folgen¬ dermaßen hergestellt wurden:The evaluation of the coloristic properties was carried out on lacquers which were produced as follows:
Eine Mischung aus 50 g der jeweiligen Pigmentzubereitung und 200 g Alkyd-Melamin- Einbrennlack (45 Gew.-% Feststoffanteil) wurde mit 300 g Glaskugeln (3 mm Durch¬ messer) 90 min mit einem Skandexgerät geschüttelt, dann auf AIuminium-Q-Panels deckend appliziert (Filmausziehgerät Typ 238 II, Fa. Erichsen) und 30 min bei 1300C eingebrannt. Die Bestimmung des Farbwinkels h wurde mit einem Spektralphotometer Spectrolino (Fa. Gretag-Macbeth) vorgenommen.A mixture of 50 g of the respective pigment preparation and 200 g of alkyd melamine stoving lacquer (45% by weight solids) was shaken with 300 g glass beads (3 mm diameter) for 90 minutes with a Skandex instrument, then on aluminum Q panels applied blanket (Filmausziehgerät type 238 II, Fa. Erichsen) and baked at 130 0 C for 30 min. The color angle h was determined using a spectrophotometer Spectrolino (Gretag-Macbeth).
Die Bestimmung der Farbstärke (Angabe der Färbeäquivalente FAE, DIN 53235) er¬ folgte farbmetrisch über die Weißaufhellung des Lacks. Dazu wurden 200 g Alkyd- Melamin-Einbrennlack mit 50 g Titandioxid 2310 (Fa. Kronos) und 5 g der jeweiligen Pigmentzubereitung mit 300 g Glaskugeln (3 mm Durchmesser) 90 min mit einem Skandexgerät geschüttelt, dann auf Aluminium-Q-Panels deckend appliziert (Filmaus- ziehgerät Typ 238 II, Fa. Erichsen) und 30 min bei 1300C eingebrannt.The determination of the color intensity (specification of the dyeing equivalents FAE, DIN 53235) er¬ followed colorimetrically on the whitening of the paint. For this purpose, 200 g of alkyd melamine stoving enamel with 50 g of titanium dioxide 2310 (Kronos) and 5 g of the respective pigment preparation with 300 g of glass beads (3 mm diameter) were shaken for 90 min with a Skandex apparatus, then applied to aluminum Q panels (Film Extractor Type 238 II, Erichsen) and baked at 130 0 C for 30 min.
Den jeweils analogen Lackierungen, die aus Einzelanreibungen der organischen und anorganischen Pigmente hergestellt wurden:The respective analogous coatings, which were produced from individual abrasions of the organic and inorganic pigments:
Standard Orange: 10 Gew. -Teile Cl. Pigment Yellow 139, 31,5 Gew.-Teile Cl.Standard Orange: 10 parts by weight Cl. Pigment Yellow 139, 31.5 parts by weight of Cl.
Pigment Orange 67, 58,5 Gew.-Teile Cl. Pigment Brown 24 Standard Rot: 63 Gew.-Teile Cl. Pigment Red 170, 36 Gew.-Teile Cl. Pig¬ ment Brown 24, 1 Gew.-Teil Cl. Pigment Yellow 42Pigment Orange 67, 58.5 parts by weight of Cl. Pigment Brown 24 Standard Red: 63 parts by weight Cl. Pigment Red 170, 36 parts by weight of Cl. Pigment Brown 24, 1 part by weight of Cl. Pigment Yellow 42
wurde der FAE-Wert 100 (Standard) zugeordnet. FAE-Werte < 100 bedeuten eine hö¬ here Farbstärke als beim Standard, FAE-Wert > 100 entsprechend eine kleinere Farb¬ stärke.the FAE value has been assigned 100 (default). FAE values <100 mean a higher color strength than the standard, FAE value> 100 correspondingly a smaller color intensity.
Zur Bestimmung der Wetterechtheit wurden die lackierten Bleche 2000 h lang in einem Xenotest 1200 (Gerät der Fa. Heraeus) gemäß EN ISO 4892-2 belastet. Die Farbände¬ rung der bewitterten Bleche wurde anschließend nach der Grauskala gemäß ISO 105- A02 beurteilt. Diese Skala reicht von Note 5 (unveränderte Lackierung) bis Note 1 (stark veränderte Lackierung).To determine the weather fastness, the painted sheets were loaded for 2000 hours in a Xenotest 1200 (device from Heraeus) in accordance with EN ISO 4892-2. The color change of the weathered sheets was then assessed according to the gray scale according to ISO 105-A02. This scale ranges from grade 5 (unchanged finish) to grade 1 (heavily modified finish).
Die Ergebnisse dieser Prüfungen sind in Tabelle 2 zusammengestellt.The results of these tests are summarized in Table 2.
Tabelle 2Table 2
Figure imgf000009_0001
Figure imgf000010_0001
Figure imgf000009_0001
Figure imgf000010_0001

Claims

Patentansprüche claims
1. Pulverförmige Pigmentzubereitungen für den Farbtonbereich von Rot bis Orange, entsprechend einem CIELAB Farbwinkel h von - 20 bis 60°, die als wesentliche Komponenten1. Powdered pigment preparations for the color range from red to orange, corresponding to a CIELAB color angle h of - 20 to 60 °, which are essential components
(A) 20 bis 99 Gew.-% mindestens eines feinteiligen organischen Pigments, ausgewählt aus der Gruppe der Pyrazolonchinazolonpigmente, Isoindolin- pigmente, Azopigmente, Diketopyrrolopyrrolpigmente und Chinophthalon- pigmente,(A) 20 to 99% by weight of at least one finely divided organic pigment selected from the group of the pyrazolonequinazolone pigments, isoindoline pigments, azo pigments, diketopyrrolopyrrole pigments and quinophthalone pigments,
undand
(B) 1 bis 80 Gew.-% mindestens eines anorganischen Pigments mit einer Mohs'schen Härte > 5,(B) 1 to 80% by weight of at least one inorganic pigment having a Mohs hardness> 5,
enthalten und durch intensives trockenes Mischen der Pigmente (A) und (B) er¬ hältlich sind.and are obtainable by intensive dry mixing of the pigments (A) and (B).
2. Pigmentzubereitungen nach Anspruch 1 , die als Komponente (B) mindestens ein Pigment aus der Gruppe Rutil und Rutilmischphasenpigmente enthalten.2. Pigment preparations according to claim 1, which contain as component (B) at least one pigment from the group of rutile and rutile mixed phase pigments.
3. Pigmentzubereitungen nach Anspruch 1 oder 2, die als Komponente (A) mindes¬ tens ein organisches Pigment mit einer mittleren Teilchengröße < 500 nm enthal- ten.3. Pigment preparations according to claim 1 or 2, which contain at least one organic pigment having an average particle size of <500 nm as component (A).
4. Verfahren zur Herstellung von Pigmentzubereitungen gemäß den Ansprüchen 1 bis 3, dadurch gekennzeichnet, daß man organisches Pigment (A) und anorgani¬ sches Pigment (B) intensiv trocken mischt.4. A process for the preparation of pigment preparations according to claims 1 to 3, characterized in that one mixes dry organic pigment (A) and anorgani¬ cal pigment (B).
5. Verfahren nach Anspruch 4, dadurch gekennzeichnet, daß man es in einem Kol¬ ler oder einem Mischer, in den Messerköpfe eingebaut sein können, durchführt.5. The method according to claim 4, characterized in that it is in a Kol¬ ler or a mixer, can be installed in the cutter heads performs.
6. Verfahren nach Anspruch 4, dadurch gekennzeichnet, daß man es in einem KoI- ler durchführt und eine kurze Mahlung in einer Stiftmühle anschließt.6. The method according to claim 4, characterized in that it is carried out in a KoI- ler and followed by a brief grinding in a pin mill.
7. Verwendung von Pigmentzubereitungen gemäß den Ansprüchen 1 bis 3 zur Ein- färbung von Lacken, Druckfarben, Kunststoffen, Baustoffen und Zubereitungen der dekorativen Kosmetik. 7. Use of pigment preparations according to claims 1 to 3 for coloring of paints, printing inks, plastics, building materials and preparations of decorative cosmetics.
PCT/EP2005/008410 2004-08-20 2005-08-03 Powdery pigment preparations for the hue range from red to orange WO2006021301A1 (en)

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4222788A (en) * 1978-01-24 1980-09-16 Basf Farben & Fasern Ag Mixed pigment and process of preparing the same
US4226634A (en) * 1978-01-24 1980-10-07 Basf Farben & Fasern Ag Process for preparing pigment compositions
US4486237A (en) * 1982-02-22 1984-12-04 Montefluous S.P.A. Composite pigments and process for their preparation
EP0212361A2 (en) * 1985-08-10 1987-03-04 Bayer Ag Pigment preparations
EP0816440A1 (en) * 1996-06-17 1998-01-07 Ciba SC Holding AG Bismuth-vanadat pigment powder mixtures
EP0985712A1 (en) * 1998-09-10 2000-03-15 Basf Aktiengesellschaft Pigment preparations in granulated form
WO2002055610A1 (en) * 2000-09-29 2002-07-18 Engelhard Corporation Co-processed yellow pigments
WO2004078852A1 (en) * 2003-03-05 2004-09-16 Heubach Gmbh Pigment preparation and method for producing the same
WO2005028564A1 (en) * 2003-09-12 2005-03-31 Clariant Produkte (Deutschland) Gmbh Pigment compositions consisting of organic and inorganic pigments

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4222788A (en) * 1978-01-24 1980-09-16 Basf Farben & Fasern Ag Mixed pigment and process of preparing the same
US4226634A (en) * 1978-01-24 1980-10-07 Basf Farben & Fasern Ag Process for preparing pigment compositions
US4486237A (en) * 1982-02-22 1984-12-04 Montefluous S.P.A. Composite pigments and process for their preparation
EP0212361A2 (en) * 1985-08-10 1987-03-04 Bayer Ag Pigment preparations
EP0816440A1 (en) * 1996-06-17 1998-01-07 Ciba SC Holding AG Bismuth-vanadat pigment powder mixtures
EP0985712A1 (en) * 1998-09-10 2000-03-15 Basf Aktiengesellschaft Pigment preparations in granulated form
WO2002055610A1 (en) * 2000-09-29 2002-07-18 Engelhard Corporation Co-processed yellow pigments
WO2004078852A1 (en) * 2003-03-05 2004-09-16 Heubach Gmbh Pigment preparation and method for producing the same
WO2005028564A1 (en) * 2003-09-12 2005-03-31 Clariant Produkte (Deutschland) Gmbh Pigment compositions consisting of organic and inorganic pigments

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