DE1234234B - Use of acidic organic phosphorus compounds as dispersants for powdery substances - Google Patents

Use of acidic organic phosphorus compounds as dispersants for powdery substances

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Publication number
DE1234234B
DE1234234B DEN9524A DEN0009524A DE1234234B DE 1234234 B DE1234234 B DE 1234234B DE N9524 A DEN9524 A DE N9524A DE N0009524 A DEN0009524 A DE N0009524A DE 1234234 B DE1234234 B DE 1234234B
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Prior art keywords
phosphorus compounds
powder
dispersants
powdery substances
acidic organic
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DEN9524A
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German (de)
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Jan Anton Willem Van Laar
Sjerp Onne Troelstra
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Koninklijke Philips NV
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Philips Gloeilampenfabrieken NV
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Publication of DE1234234B publication Critical patent/DE1234234B/en
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09CTREATMENT 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
    • C09C3/00Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/08Treatment with low-molecular-weight non-polymer organic compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09CTREATMENT 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
    • C09C3/00Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/006Combinations of treatments provided for in groups C09C3/04 - C09C3/12
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B5/00Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
    • G11B5/62Record carriers characterised by the selection of the material
    • G11B5/68Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent
    • G11B5/70Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer
    • G11B5/7013Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer characterised by the dispersing agent
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B5/00Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
    • G11B5/62Record carriers characterised by the selection of the material
    • G11B5/68Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent
    • G11B5/70Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer
    • G11B5/702Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer characterised by the bonding agent
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B5/00Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
    • G11B5/62Record carriers characterised by the selection of the material
    • G11B5/68Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent
    • G11B5/70Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer
    • G11B5/706Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer characterised by the composition of the magnetic material
    • G11B5/70626Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer characterised by the composition of the magnetic material containing non-metallic substances
    • G11B5/70642Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer characterised by the composition of the magnetic material containing non-metallic substances iron oxides
    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B5/00Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
    • G11B5/62Record carriers characterised by the selection of the material
    • G11B5/68Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent
    • G11B5/70Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer
    • G11B5/712Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer characterised by the surface treatment or coating of magnetic particles
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01FMAGNETS; INDUCTANCES; TRANSFORMERS; SELECTION OF MATERIALS FOR THEIR MAGNETIC PROPERTIES
    • H01F1/00Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties
    • H01F1/44Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties of magnetic liquids, e.g. ferrofluids
    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01PINDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00Particle morphology
    • C01P2004/80Particles consisting of a mixture of two or more inorganic phases

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Power Engineering (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Paints Or Removers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Description

Verwendung von sauren organischen Phosphorverbindungen als Dispergiermittel für pulverförmige Stoffe Bekannt ist ein Verfahren zur Herstellung einer zum Auftragen auf Putz geeigneten Farbe; um eine bessere Vermischung der Pigmente und Träger und demzufolge eine größere Intensität und Homogenität der Farbe zu erlangen, sollen hiernach die Pigmente und Träger in Wasser unter Zusatz eines wasserlöslichen Salzes eines Esters von Phosphorsäure vermischt werden; nach Trocknung dieser Dispersion kann der Rückstand in einem Öl dispergiert werden.Use of acidic organic phosphorus compounds as dispersants for powdery substances A method for producing one for application is known suitable paint on plaster; a better mixing of the pigments and carriers and consequently a greater intensity and homogeneity of the color should be achieved then the pigments and carriers in water with the addition of a water-soluble salt an ester of phosphoric acid are mixed; after drying this dispersion the residue can be dispersed in an oil.

Wie bekannt (Verweij und Overbeek, Elsevier Publishing Company Inc., 1948, S. 13 bis 18), bereitet eine homogene Verteilung von Pulverteilchen in einer organischen Flüssigkeit Schwierigkeiten, da die Pulverteilchen mehr oder weniger aggregieren. Das Entstehen von Aggregaten von in Flüssigkeit suspendierten Teilchen hat zur Folge, daß die Niederschlaggeschwindigkeit groß ist und ein voluminöser Bodensatz entsteht, der häufig eine einer plastischen Masse entsprechende Viskosität hat.As known (Verweij and Overbeek, Elsevier Publishing Company Inc., 1948, pp. 13 to 18), prepares a homogeneous distribution of powder particles in one organic liquid difficulties, as the powder particles more or less aggregate. The formation of aggregates of particles suspended in liquid has the consequence that the precipitation rate is high and a more voluminous Sediment arises, which often has a viscosity corresponding to a plastic mass Has.

Werden aber keine Aggregate gebildet, so ist die Niederschlaggeschwindigkeit der suspendierten Teilchen gering. Es entsteht dann ein wenig voluminöser Bodensatz, der die »dilatancy«-Erscheinung aufweist, worunter hier verstanden wird, daß bei einer langsamen Formänderung der Bodensatz sich wie eine etwas viskose Flüssigkeit verhält, während bei einer schnellen Formänderung der Bodensatz die Fließeigenschaften einer zähen Masse annimmt. Es ist also anzustreben, diese Neigung zur Bildung von Aggregaten zu unterdrücken, so daß man die Eigenschaften einer Suspension in organischen Flüssigkeiten und des aus dieser entstandenen Bodensatzes in den obenerwähnten Hinsichten ändern kann. Dieses Ziel läßt sich erreichen, wenn als Dispergiermittel für pulverförmige Stoffe in organischen Verbindungen saure organische Phosphorverbindungen verwendet werden, in denen erfindungsgemäß ein Phosphoratom wenigstens eine Hydroxylgruppe und wenigstens einen Alkyl-, Aryl- oder Aralkyl-, Alkoxyaroxy- oder Aralkoxyrest trägt und die übrigbleibenden Valenzen von Wasserstoff oder Sauerstoff abgesättigt sein können.If, however, no aggregates are formed, the precipitation rate is of suspended particles is low. A little voluminous sediment then arises, which has the "dilatancy" appearance, which is understood here to mean that at a slow change in shape the sediment turns out to be a somewhat viscous liquid behaves, while with a rapid change in shape the sediment affects the flow properties assumes a viscous mass. The aim is therefore to reduce this tendency towards the formation of Suppress aggregates, so that one has the properties of a suspension in organic Liquids and the sediment resulting from them in the above-mentioned respects can change. This goal can be achieved when used as a dispersant for powdery Substances in organic compounds used acidic organic phosphorus compounds in which, according to the invention, a phosphorus atom has at least one hydroxyl group and at least one alkyl, aryl or aralkyl, alkoxyaroxy or aralkoxy radical carries and saturates the remaining valences of hydrogen or oxygen could be.

Geeignete Phosphorsäurederivate sind die mono-und diorthophosphorsauren Ester, wie die Ester von Orthophosphorsäure und Butanol-l, Butanol-2, Isobutanol-1, n-Pentanol-l, n-Hexanol-1, 2-Äthylhexanol-1, Dekanol-1, Phenol, Kresol (o-, m- und p-), Xylenol und Kardanol.Suitable phosphoric acid derivatives are the mono- and diorthophosphoric acids Esters, such as the esters of orthophosphoric acid and 1-butanol, 2-butanol, 1-isobutanol, n-pentanol-1, n-hexanol-1, 2-ethylhexanol-1, decanol-1, phenol, cresol (o-, m- and p-), xylenol and cardanol.

Andere geeignete Phosphorverbindungen sind die eine oder zwei Kohlenwasserstoffgruppen tragenden Phosphonsäuren, z. B. Mono- und Dihexanphosphonsäure, Mono- und Distyrolphosphonsäure und Dibenzylphosphonsäure.Other suitable phosphorus compounds are the one or two hydrocarbon groups bearing phosphonic acids, e.g. B. mono- and dihexanephosphonic acid, mono- and distyrene phosphonic acid and dibenzylphosphonic acid.

Wenn die flüssige Phase im wesentlichen aus Stoffen mit einem vorwiegend aromatischen Charakter besteht, so werden vorzugsweise diejenigen Phosphorsäurederivate angewendet, deren organischer Rest einen vorwiegend aromatischen Charakter hat. So eignen sich die Mono- und Di-, Phenol-, Kresol- und Xylenolester von Orthophosphorsäure besonders zum Verteilen von Pulvern in Benzol, Toluol und Xylol, da kleinere Mengen solcher Phosphorsäurederivate das Aggregieren der Teilchen in höherem Maße verhüten als entsprechende Mengen solcher Phosphorsäurederivate, deren organischer Rest einen vorwiegend aliphatischen Charakter hat. Letztere Verbindungen dagegen sind vorzuziehen, wenn die flüssige Phase im wesentlichen oder völlig aus Verbindungen mit einem vorwiegend ahphatischen Charakter bestehen, wie Benzin, Paraffinöl, Methyläthylketon. Die Phosphorsäurederivate, deren organischer Rest aus Methyl- und Äthylgruppen besteht, haben gewöhnlich einen geringeren Effekt, und man verwendet daher vorzugsweise Phosphorsäurederivate, bei denen ein an einem Phosphoratom gebundener organischer Rest wenigstens 4 Kohlenstoffatome enthält. Die erfindungsgemäß verwendeten Phosphorverbindungen werden in Mengen von 2 bis 10 mg je Gramm des zu verteilenden Pulvers angewendet. Wird diese Menge vergrößert, so entsteht im allgemeinen eine weiter abnehmende Neigung zum Bilden von Aggregaten. Ein Zusatz von 5 bis 25 mg je Gramm des zu verteilenden Pulvers ergibt in den meisten Fällen die günstigste Wirkung.When the liquid phase consists essentially of substances with a predominantly If there is an aromatic character, those phosphoric acid derivatives are preferred used, the organic residue of which has a predominantly aromatic character. The mono- and di-, phenolic, cresol and xylenol esters of orthophosphoric acid are suitable especially for distributing powders in benzene, toluene and xylene, since smaller quantities of such phosphoric acid derivatives prevent aggregation of the particles to a greater extent as corresponding amounts of such phosphoric acid derivatives, the organic radical of which is a predominantly aliphatic in character. The latter connections, on the other hand, are preferable, when the liquid phase consists essentially or entirely of compounds with a predominantly There are ahphatic characters, such as gasoline, paraffin oil, methyl ethyl ketone. The phosphoric acid derivatives, whose organic residue consists of methyl and ethyl groups usually have one lesser effect, and it is therefore preferred to use phosphoric acid derivatives where an organic radical bonded to a phosphorus atom has at least 4 carbon atoms contains. The phosphorus compounds used in the present invention are used in amounts of 2 to 10 mg per gram of powder to be distributed. Will If this amount increases, there is generally a further decreasing tendency to form aggregates. An addition of 5 to 25 mg per gram of the to be distributed Powder gives the most beneficial effect in most cases.

Die günstigsten Ergebnisse werden erreicht, wenn Pulver mit säurebindenden Eigenschaften verteilt werden sollen, wie viele Metallpulver, Pulver von basischen Oxyden, Sulfiden und von Salzen einer starken Base und einer schwachen Säure.The best results are achieved when powder containing acid-binding Properties should be distributed like many metal powder, powder of basic Oxides, sulphides and salts of a strong base and a weak acid.

Solche Pulver reagieren wahrscheinlich an der Oberfläche der Pulverteilchen mit den zu verwendenden Phosphorverbindungen, so daß diese mit einer fest gebundenen Schicht der verwendeten Phosphorverbindung überdeckt werden.Such powders are likely to react on the surface of the powder particles with the phosphorus compounds to be used, so that these are firmly bound with a Layer of the phosphorus compound used are covered.

Es wurde festgestellt, daß bei Anwendung von säurebindenden Pulvern die Phosphorverbindungen mit mehr als einer sauren Funktion gewöhnlich eine bessere Auswirkung haben, so daß diese bevorzugt verwendet werden.It has been found that when using acid-binding powders the phosphorus compounds with more than one acidic function usually have a better one Have an effect, so that these are preferably used.

Derartige Dispersionen eignen sich besonders bei der Herstellung von Farbsuspensionen, da hierdurch die Mahlbearbeitung zum Verteilen von Farbpigmenten in einer organischen Flüssigkeit häufig wesentlich abgekürzt werden kann und eine Farbe mit einer geringeren Neigung der Pigmentteilchen zum Senken entsteht.Such dispersions are particularly suitable in the production of Color suspensions, as this results in the grinding process for distributing color pigments in an organic liquid can often be substantially abbreviated and a Color is produced with a lower tendency of the pigment particles to sink.

Vorzugsweise wird die gewählte Phosphorverbindung in der flüssigen Phase in Lösung gebracht. Jedoch kann man auch die Pulver mit einer Phosphorverbindung behandeln und darauf in einer organischen Flüssigkeit verteilen. Die Phosphorverbindungen eignen sich besonders beim Verteilen von magnetischen Pulvern in einer organischen Flüssigkeit, da solche Pulver verstärkt Aggregate bilden.Preferably the selected phosphorus compound is in the liquid Phase brought into solution. However, you can also use the powder with a phosphorus compound treat and distribute it in an organic liquid. The phosphorus compounds are particularly suitable when distributing magnetic powders in an organic Liquid, since such powders increasingly form aggregates.

Wohl ist ein Zusatz von Phosphorsäure zu pigmentierten Lacken bekannt, um ein hartes Absetzen der Pigmente im Lack zu verhindern. Zur Verhinderung von Aggregatbindung hat sich jedoch die Phosphorsäure ebenso wie Phosphoniumverbindungen in vielen Fällen als unwirksam erwiesen.An addition of phosphoric acid to pigmented paints is well known, to prevent the pigments from settling hard in the paint. To prevent However, phosphoric acid has aggregate binding as well as phosphonium compounds proven ineffective in many cases.

Beispiel 1 In einer Kugelmühle wird i00 g pulverförmiges Eisenoxyd (Fe#-,03) in 11 Benzol gemahlen. Nach 10stündigem Mahlen ergibt sich, daß die Suspension sich noch innerhalb weniger Minuten völlig zu einer voluminösen flockigen Masse niederschlägt. Wird dann noch 1 g Monostyrolphosphonsäure der Formel zugesetzt und zwei weitere Stunden gemahlen, so ist eine Suspension entstanden, die erst nach einigen Stunden völlig zu einem kompakten Bodensatz niedergeschlagen ist.EXAMPLE 1 100 g of powdered iron oxide (Fe # - .03) are ground in 11 of benzene in a ball mill. After grinding for 10 hours, the result is that the suspension is completely precipitated into a voluminous, flaky mass within a few minutes. Then add 1 g of monostyrene phosphonic acid of the formula added and ground for a further two hours, the result is a suspension which is completely precipitated to a compact sediment only after a few hours.

Beispiel 2 Eine Suspension von 100g feinem Fe203-Pulver in 11 Methyläthylketon ist nach einigen Stunden völlig niedergeschlagen. Wird in der Flüssigkeit 1 g eines Gemisches von Mono- und Dibutylorthophosphorsäure in Lösung gebracht und das Pulver von neuem suspendiert, so ist die Suspension nach Verlauf eines Monats noch nicht völlig niedergeschlagen. Der kompakte Bodensatz läßt sich aber durch Schütteln gleichmäßig über die Flüssigkeit verteilen.EXAMPLE 2 A suspension of 100 g of fine Fe 2 O 3 powder in 11 methyl ethyl ketone is completely precipitated after a few hours. If 1 g of a mixture of mono- and dibutylorthophosphoric acid is dissolved in the liquid and the powder is suspended again, the suspension is not completely precipitated after a month. The compact sediment can be evenly distributed over the liquid by shaking it.

Beispiel 3 50g eines verhältnismäßig grobkörnigen Titandioxydpulvers wird in 500 ccm Benzol suspendiert, in dem 1 g Monokardanylphosphorsäure der Formel in Lösung gebracht ist. Nach 12 Stunden ist die Suspension noch nicht zur Hälfte niedergeschlagen. Beispiel 4 100 g Cr203-Pulver wird in 1 1 Methyläthylketon suspendiert, in dem 1 g Monokardanylphosphorsäure der Formel in Lösung gebracht ist. Erst nach Verlauf einer Woche hat sich ein deutlich sichtbarer Bodensatz gebildet. Nach 2 Wochen aber war das Pulver noch nicht völlig niedergeschlagen.Example 3 50 g of a relatively coarse-grained titanium dioxide powder is suspended in 500 cc of benzene in which 1 g of monocardanyl phosphoric acid of the formula is brought into solution. After 12 hours, the suspension is not yet half precipitated. Example 4 100 g of Cr 2 O 3 powder is suspended in 1 liter of methyl ethyl ketone in which 1 g of monocardanyl phosphoric acid of the formula is brought into solution. Only after a week has a clearly visible sediment formed. After 2 weeks, however, the powder was not yet completely depressed.

Beispiel 5 100 g Crz03-Pulver wird mit 10 g Polyvinylchlorid und 50 ccm Amylacetat-Aceton (1 : 1) gemahlen. Der entstandene Lack ist thixotropisch und ergibt eine unregelmäßige Bedeckung auf der Innenwand der Flasche, in der der Lack geschüttelt wird. Ein Zusatz von 1 g Dikresylphosphorsäure bewirkt aber eine völlige Beseitigung der Thixotropie, und nach dem Schütteln ergibt sich, daß das Pigment gleichmäßig durch die Flüssigkeit verteilt ist.Example 5 100 g of Crz03 powder is mixed with 10 g of polyvinyl chloride and 50 ccm amyl acetate-acetone (1: 1) ground. The resulting varnish is thixotropic and results in an irregular coverage on the inner wall of the bottle in which the lacquer is shaken. An addition of 1 g of dicresyl phosphoric acid, however, causes a complete Eliminate the thixotropy, and after shaking it results in the pigment is evenly distributed through the liquid.

Beispiel 6 80g magnetisches Feü03-Pulver wird in 20g Vinylchlorid-Vinylacetat-Copolymer in `einem Gemisch von 40 ccm Aceton und 80 ccm Benzol in Lösung gebracht. Es entsteht eine dicke tonartige Masse. Mischt man diese Masse mit 1 g Dikresylorthophosphorsäure, so wird die Masse leicht flüssig und kann bequem in einer gleichmäßig starken Schicht auf einen Träger aufgebracht werden.Example 6 80g Feü03 magnetic powder is brought into 20g vinyl chloride-vinyl acetate copolymer in `a mixture of 40 cc of acetone and 80 cc of benzene in solution. A thick clay-like mass is created. If this mass is mixed with 1 g of dicresyl orthophosphoric acid, the mass becomes easily liquid and can easily be applied to a support in a uniformly thick layer.

Claims (1)

Patentanspruch: Verwendung von sauren organischen Phosphorverbindungen, in denen ein Phosphoratom wenigstens eine Hydroxylgruppe und wenigstens einen Alkyl-, Aryl-, Aralkyl-, Alkoxyaroxy- oder Aralkoxyrest trägt und übrigbleibende Valenzen mit Wasserstoff oder Sauerstoff abgesättigt sind, als Dispergiermittel für pulverförmige Stoffe in organischen Flüssigkeiten in Mengen von 5 bis 25 mg je Gramm des zu verteilenden Pulvers.Claim: Use of acidic organic phosphorus compounds, in which a phosphorus atom has at least one hydroxyl group and at least one alkyl, Aryl, aralkyl, alkoxyaroxy or aralkoxy radical carries and remaining valences are saturated with hydrogen or oxygen, as a dispersant for powdery Substances in organic liquids in amounts of 5 to 25 mg per gram of the to be distributed Powder.
DEN9524A 1953-09-29 1954-09-27 Use of acidic organic phosphorus compounds as dispersants for powdery substances Pending DE1234234B (en)

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NL1234234X 1953-09-29
NL766484X 1953-09-29

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL8120319A (en) * 1980-08-28 1982-07-01 Toyo Inc Mfg Co Ltd MAGNETIC REGISTRATION MEDIUM.
EP0075083A2 (en) * 1981-09-21 1983-03-30 International Business Machines Corporation Magnetic recording coating composition
US6713543B2 (en) 2000-11-27 2004-03-30 Millennium Inorganic Chemicals, Inc. Pigments treated with organo-phosphoric acids and their salts
WO2007017199A2 (en) * 2005-08-05 2007-02-15 Eckart Gmbh Surface-coated pearlescent pigments, method for the production thereof, and use thereof
US7819966B2 (en) 2005-08-05 2010-10-26 Eckart Gmbh Surface-coated pearlescent pigments, process for preparing them, and their use
US7955772B2 (en) 2004-11-22 2011-06-07 Eckart Gmbh Dry toner, processes for the production thereof, and the use thereof

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GB1058426A (en) * 1964-08-24 1967-02-08 Agfa Gevaert Nv Process for the manufacture of magnetizable recording layers
DE3619746A1 (en) * 1986-06-12 1987-12-17 Basf Ag SUPER PARAMAGNETIC SOLID PARTICLES

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DE619019C (en) * 1929-04-06 1935-09-20 Boehme Fettchemie Ges M B H Process for the production of acidic phosphoric acid esters of high molecular weight aliphatic alcohols
FR852323A (en) * 1938-04-27 1940-01-30 Ig Farbenindustrie Ag Coatings paints
DE696317C (en) * 1930-08-12 1940-09-18 I G Farbenindustrie Akt Ges eestern
US2219395A (en) * 1937-06-24 1940-10-29 Ici Ltd Manufacture of pigmented oil compositions
US2224695A (en) * 1938-11-25 1940-12-10 Carl F Prutton Inhibitor
DE740054C (en) * 1942-04-08 1943-10-11 Rassbach & Kralle Ag Process for the production of non-settling pigmented paints
AT174610B (en) * 1950-05-31 1953-04-25 Ici Ltd Process for the preparation of new esters of aryl phosphoric acid and their salts

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE619019C (en) * 1929-04-06 1935-09-20 Boehme Fettchemie Ges M B H Process for the production of acidic phosphoric acid esters of high molecular weight aliphatic alcohols
DE696317C (en) * 1930-08-12 1940-09-18 I G Farbenindustrie Akt Ges eestern
US2219395A (en) * 1937-06-24 1940-10-29 Ici Ltd Manufacture of pigmented oil compositions
FR852323A (en) * 1938-04-27 1940-01-30 Ig Farbenindustrie Ag Coatings paints
US2224695A (en) * 1938-11-25 1940-12-10 Carl F Prutton Inhibitor
DE740054C (en) * 1942-04-08 1943-10-11 Rassbach & Kralle Ag Process for the production of non-settling pigmented paints
AT174610B (en) * 1950-05-31 1953-04-25 Ici Ltd Process for the preparation of new esters of aryl phosphoric acid and their salts

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL8120319A (en) * 1980-08-28 1982-07-01 Toyo Inc Mfg Co Ltd MAGNETIC REGISTRATION MEDIUM.
EP0075083A2 (en) * 1981-09-21 1983-03-30 International Business Machines Corporation Magnetic recording coating composition
EP0075083A3 (en) * 1981-09-21 1983-08-17 International Business Machines Corporation Magnetic recording coating composition
US6713543B2 (en) 2000-11-27 2004-03-30 Millennium Inorganic Chemicals, Inc. Pigments treated with organo-phosphoric acids and their salts
US6765041B1 (en) 2000-11-27 2004-07-20 Millenium Inorganic Chemicals, Inc. Organo-acid phosphate treated pigments
US6825251B2 (en) 2000-11-27 2004-11-30 Millennium Inorganic Chemicals, Inc. Organo-acid phosphate treated pigments
US7259195B2 (en) 2000-11-27 2007-08-21 Millennium Inorganic Chemicals, Inc. Pigments treated with organo-phosphoric acids and their salts
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WO2007017199A2 (en) * 2005-08-05 2007-02-15 Eckart Gmbh Surface-coated pearlescent pigments, method for the production thereof, and use thereof
WO2007017199A3 (en) * 2005-08-05 2007-05-18 Eckart Gmbh & Co Kg Surface-coated pearlescent pigments, method for the production thereof, and use thereof
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BE532146A (en) 1955-03-28
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