EP1156780A1 - Hydrophobic, rheologically active agent, method for producing the same and use thereof - Google Patents

Hydrophobic, rheologically active agent, method for producing the same and use thereof

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Publication number
EP1156780A1
EP1156780A1 EP00912474A EP00912474A EP1156780A1 EP 1156780 A1 EP1156780 A1 EP 1156780A1 EP 00912474 A EP00912474 A EP 00912474A EP 00912474 A EP00912474 A EP 00912474A EP 1156780 A1 EP1156780 A1 EP 1156780A1
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EP
European Patent Office
Prior art keywords
hydrophobic
ethyl
clay minerals
ion
rheologically active
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP00912474A
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German (de)
French (fr)
Inventor
Rémy A. CHAPERON
Jean-Pierre Abgottspon
Roland Antony
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Individual
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Individual
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Priority claimed from DE1999108006 external-priority patent/DE19908006C1/en
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Publication of EP1156780A1 publication Critical patent/EP1156780A1/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26—Aluminium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B33/00—Silicon; Compounds thereof
    • C01B33/20—Silicates
    • C01B33/36—Silicates having base-exchange properties but not having molecular sieve properties
    • C01B33/38—Layered base-exchange silicates, e.g. clays, micas or alkali metal silicates of kenyaite or magadiite type
    • C01B33/44—Products obtained from layered base-exchange silicates by ion-exchange with organic compounds such as ammonium, phosphonium or sulfonium compounds or by intercalation of organic compounds, e.g. organoclay material

Definitions

  • the literature also contains the information that poor quality organobentonites can also be produced in the kneader by directly reacting the solid starting materials bentonite with N, N-dialkyldimethylammonium chloride.
  • the products obtained in this way are used in particular as thixotropic agents for a wide variety of purposes and have so far proven themselves.
  • a major disadvantage of these thixotropic agents and the by-products formed during their production is their very poor biodegradability. This also poses corrosion risks in many applications Presence of, albeit seemingly small amounts, chloride ions, which cannot be removed even with considerable washing effort.
  • the commercial forms of N, N-dialkyldimethylammonium chloride contain up to 15% 2-propanol, which, when used to produce organobentonites, entails additional risks and environmental problems.
  • the commercial products Noxamium 91, 920 and 960 contain certain amounts of 2-propanol. It is possible to remove this 2-propanol beforehand, for example by distillation. The reaction described above is still the same. Completely 2-propanol-free end products are thus obtained.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Inorganic Chemistry (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)

Abstract

The invention relates to a hydrophobic, rheologically active agent based on clays and/or clay minerals which are capable of ion-exchange. The inventive agent contains N,N-di(acyloxy-2-ethyl)-N-hydroxy-2-ethyl-N-methylammonium methosulfates, methylammonium methophosphates, and/or methylammonium dimethophosphates as hydrophobing cations. Hydrophobic thixotropic agents are produced when using bentonites and these cations. Said thixotropic agents are free from chloride and are well-suited for use in technical, cosmetic and medical-pharmaceutical products.

Description

Hydrophobe, Theologisch wirksame Mittel, Verfahren zur ihrer Herstellung und ihre Verwendung Hydrophobic, theologically active agents, processes for their preparation and their use
Gegenstand der vorliegenden Erfindung sind hydrophobe, Theologisch wirksame Mittel auf Basis von ionenaustauschfähigen Tonen und/oder Tonmineralien, welche hydrophobierende Kationen enthalten. Weiterhin betrifft die Erfindung Verfahren zur Herstellung dieser Mittel und ihre Verwendung.The present invention relates to hydrophobic, theologically active agents based on ion-exchangeable clays and / or clay minerals which contain hydrophobic cations. The invention further relates to processes for the preparation of these compositions and their use.
Hydrophobe, rheologisch wirksame Mittel auf Basis von ionenaustauschfähigen Tonen und/oder Tonmineralien sind bekannt. Sie werden bisher hergestellt durch Umsetzung von ionenaustauschfähigen Tonen und/oder Tonmineralien, insbesondere Bentoniten, wobei diese Montmorillonit oder Hectorit als Hauptbestandteile enthalten, oder Attapulgiten mit quartären Ammoniumsalzen. Als quartäre Ammoniumsalze werden vor allem N,N-Dialkyl-Dimethylammonium- chloride mit der meist warmen wäßrigen Aufschlämmung des Bentonits oder Attapulgites umgesetzt.Hydrophobic, rheologically active agents based on ion-exchangeable clays and / or clay minerals are known. They have so far been produced by reacting ion-exchangeable clays and / or clay minerals, in particular bentonites, which contain montmorillonite or hectorite as main constituents, or attapulgites with quaternary ammonium salts. As quaternary ammonium salts, especially N, N-dialkyl-dimethylammonium chlorides are reacted with the mostly warm aqueous slurry of bentonite or attapulgite.
Die Literatur enthält weiter die Information, daß sich Organobentonite minderer Qualität auch durch direkte Umsetzung der festen Ausgangsstoffe Bentonit mit N,N-Dialkyl-Dimethyiammoniumchlorid im Kneter herstellen lassen. Die so erhaltenen Produkte werden insbesondere als Thixotropierungsmittel für verschiedenste Zwecke eingesetzt und haben sich bisher bewährt. Ein wesentlicher Nachteil dieser Thixotropierungsmittel und der bei ihrer Herstellung entstehenden Nebenprodukte ist deren sehr schlechte biologische Abbaubarkeit. Korrosionsrisiken bringt ferner in vielen Anwendungsfällen das Vorhandensein von, wenn auch scheinbar geringen Mengen, Chloridionen, die auch mit erheblichem Waschaufwand nicht zu beseitigen sind. Die Handelsformen des N,N-Dialkyl-dimethylammoniumchlorids enthalten aus verschiedenen Gründen bis zu 15% 2-Propanol, was bei dessen Einsatz zur Herstellung von Organobentoniten zusätzliche Risiken und Umweltprobleme bringt.The literature also contains the information that poor quality organobentonites can also be produced in the kneader by directly reacting the solid starting materials bentonite with N, N-dialkyldimethylammonium chloride. The products obtained in this way are used in particular as thixotropic agents for a wide variety of purposes and have so far proven themselves. A major disadvantage of these thixotropic agents and the by-products formed during their production is their very poor biodegradability. This also poses corrosion risks in many applications Presence of, albeit seemingly small amounts, chloride ions, which cannot be removed even with considerable washing effort. For various reasons, the commercial forms of N, N-dialkyldimethylammonium chloride contain up to 15% 2-propanol, which, when used to produce organobentonites, entails additional risks and environmental problems.
Die Erfindung hat sich die Aufgabe gestellt, hydrophobe, rheologisch wirksame Mittel auf Basis von ionenaustauschfähigen Tonen und/oder Tonmineralien zur Verfügung zu stellen, die biologisch wesentlich besser abbaubar sind, keine Chloridionen enthalten und nach Möglichkeit auch 2- propanolfrei hergestellt werden können. Sie vermögen die bisherigen Produkte in allen Bereichen, wie Farben, Lacken, Beschichtungssystemen, Bautechnik, Kosmetik, medizinisch-pharmazeutischen Produkten, Schmierstoffen usw. ohne viel Aufwand zu ersetzen.The object of the invention is to provide hydrophobic, rheologically active agents based on ion-exchangeable clays and / or clay minerals which are much more readily biodegradable, contain no chloride ions and, if possible, can also be prepared 2-propanol-free. They can replace the previous products in all areas, such as paints, varnishes, coating systems, construction technology, cosmetics, medical-pharmaceutical products, lubricants etc. without much effort.
Diese Aufgabe wird gelöst dadurch, daß die Kationen in den austauschfähigen Tonen und/oder Tonmineralien hydrophobierend wirkende Kationen der quartären Diester, nämlich der N,N-di(acyloxy-2- ethyl)-N-hydroxy-2-ethyl, N-methylammoniummethosulfate der Formel I, der -methophosphate und/oder -dimethophosphate der Formel II und III sind, in denen R Alkylgruppen darstellen.This object is achieved in that the cations in the exchangeable clays and / or clay minerals have hydrophobic cations of the quaternary diesters, namely the N, N-di (acyloxy-2-ethyl) -N-hydroxy-2-ethyl, N-methylammonium methosulfates of the formula I, the -methophosphates and / or -dimethophosphates of the formula II and III, in which R represents alkyl groups.
CH2-CH2-OHCH 2 -CH 2 -OH
II.
R-C-O-CH2-CH2 - N - CH2-CH2-O-C-R CH3-OSO3RCO-CH 2 -CH 2 - N - CH 2 -CH2-OCR CH3-OSO3
I! I I'I! I I '
O CH3 O R- CH3-O-PO3O CH 3 O R- CH 3 -O-PO3
CH2-CH2-OHCH 2 -CH 2 -OH
R-C-O-CH2-CH2 - N -CH2-CH2-O-C-F (CH3-0)2-P02 RCO-CH 2 -CH 2 - N -CH 2 -CH 2 -OCF (CH 3 -0) 2 -P0 2
II I IIII I II
O CH3 OO CH 3 O
IIIIII
Vorzugsweise bestehen die Acylgruppen hierin vorwiegend aus gesättigten und/oder ungesättigten Fettsäuren mit 8 bis 22 Kohlenstoffatomen, wobei Fettsäuren mit 16 bis 18 Kohlenstoffatomen aus tierischem und/oder pflanzlichem und/oder synthetischem Ursprung bevorzugt werden.The acyl groups here preferably consist predominantly of saturated and / or unsaturated fatty acids having 8 to 22 carbon atoms, fatty acids having 16 to 18 carbon atoms of animal and / or vegetable and / or synthetic origin being preferred.
Als ionenaustauschfähige Tone und/oder Tonmineralien werden Bentonite bevorzugt. Insbesonders kommen montmorillonit- oder hectoritreiche Ausgangsmaterialien zum Einsatz, daneben auch Attapulgite. Sie werden beispielsweise durch Windsichten und Sieben, durch Sedimentieren von Aufschlämmungen in Wasser mit 30 oder weniger g Bentonit/I Aufschlämmung oder durch Hydrozentrifugieren vorgereinigt. Wesentlich ist die Kenntnis der Ionenaustauschkapazität des gereinigten Ausgangsmaterials in mmol/100 g. Zum vollständigen Umsatz wird die gleiche Molmenge quartärer Ester der Formel I, II und/oder III in mmol eingesetzt. Das Molverhältnis beider Reaktanten kann, je nach den gewünschten Eigenschaften des Produktes von 1:1 (unpolar) bis 1:0,1 (stark polar) gewählt werden. Das so entstehende praktisch wasserunlösliche Produkt wird durch Filtration oder Zentrifugieren von der Mutterlauge getrennt und, wenn nötig, möglichst salzfrei gewaschen. Das stark wasserhaltige Produkt wird einer schonenden Trocknung unterworfen, anschließend zerkleinert und feingemahlen. Es ist im Gegensatz zu den bisherigen Organobentoniten chloridfrei. Damit entfällt jedes Risiko von Folgeschäden durch eine chloridinduzierte Korrosion. Auch der Gehalt an 2-Propanol wird dabei praktisch auf Null reduziert.Bentonites are preferred as ion-exchangeable clays and / or clay minerals. In particular, montmorillonite- or hectorite-rich starting materials are used, as well as attapulgite. They are pre-cleaned, for example, by air sifting and sieving, by sedimentation of slurries in water with 30 or less g of bentonite / l slurry or by hydrocentrifugation. Knowledge of the ion exchange capacity of the purified starting material in mmol / 100 g is essential. For complete conversion, the same molar amount of quaternary esters of the formula I, II and / or III is used in mmol. The molar ratio of the two reactants can be selected from 1: 1 (non-polar) to 1: 0.1 (strongly polar), depending on the desired properties of the product. The practical result Water-insoluble product is separated from the mother liquor by filtration or centrifugation and, if necessary, washed as salt-free as possible. The product, which contains a lot of water, is subjected to gentle drying, then crushed and finely ground. In contrast to the previous organobentonites, it is chloride-free. This eliminates any risk of consequential damage from chloride-induced corrosion. The 2-propanol content is practically reduced to zero.
Die erfindungsgemäß verwendeten quartären Ester der Formel I sind bisher nur als Textilhilfsmittel, d.h. als Weichspüler eingesetzt worden.The quaternary esters of formula I used according to the invention have so far only been used as textile auxiliaries, i.e. been used as a fabric softener.
Die Methophosphate und/oder die Dimethophosphate der Formeln II und III sind herstellbar durch Umsetzung des Zwischenproduktes N,N-di(acyl- oxy-2-ethyl)-N-hydroxy-2-ethyl-amin mit Trimethophosphit (CH3-0)3P und anschließende Oxidation mit Luftsauerstoff. Trimethophosphit ist beispielweise herstellbar aus Phosphortrichlorid und Methanol. Die Methophosphate und Dimethophosphate besitzen den Vorteil, daß sie nicht ausgewaschen werden müssen, da herstellungsbedingte Verunreinigungen durch Phosphorsäure oder Phosphorsäurederivate keine Korrosionsgefahr auslösen, sondern eher als Korrosionsschutzmittel wirken. Sie können sogar auf angerostetem Eisen zur Haftverbesserung führen und somit die Haftfestigkeit von entsprechend thixotropierten Farben verbessern. In den Fällen, wo der niedrige pH-Wert stören könnte, kann auch in diesen Fällen, beispielsweise mit Schlämmkreide neutralisiert werden. Schließlich kann auch mit Hilfe von Triethanolamin neutralisiert werden, wobei dann Triethanolaminphosphat entsteht, welches als Korrosionsinhibitor für Eisen bekannt ist. In den nachfolgenden Beispielen ist die Herstellung der erfindungsgemäßen hydrophoben, rheologisch wirksamen Mittel beschrieben. Selbstverständlich können auch andere Tone und Tonmineralien und andere N,N-di(acyloxy-2-ethyl)-N-hydroxy-2-ethyl-N-methylammonium- methosulfate, -methophosphate und/oder -dimethophosphate eingesetzt werden.The methophosphates and / or the dimethophosphates of the formulas II and III can be prepared by reacting the intermediate N, N-di (acyloxy-2-ethyl) -N-hydroxy-2-ethylamine with trimethophosphite (CH 3 -0) 3 P and subsequent oxidation with atmospheric oxygen. Trimethophosphite can be produced, for example, from phosphorus trichloride and methanol. The methophosphates and dimethophosphates have the advantage that they do not have to be washed out, since production-related impurities caused by phosphoric acid or phosphoric acid derivatives do not pose any risk of corrosion, but rather act as anti-corrosion agents. They can even improve adhesion on rusted iron and thus improve the adhesive strength of correspondingly thixotropic colors. In cases where the low pH could interfere, neutralization can also be carried out in these cases, for example with chalk. Finally, it can also be neutralized with the help of triethanolamine, which then produces triethanolamine phosphate, which is known as a corrosion inhibitor for iron. The preparation of the hydrophobic, rheologically active agents according to the invention is described in the following examples. Of course, other clays and clay minerals and other N, N-di (acyloxy-2-ethyl) -N-hydroxy-2-ethyl-N-methylammonium methosulfates, methophosphates and / or dimethophosphates can also be used.
Beispiel 1example 1
Handelsüblicher Bentonit der Firma CECA ATO (Handelsprodukte mit der Bezeichnung "Clarsol") wird entsprechend seiner praktischen Austauschkapazität in mmol/100 g im Molverhältnis 1: 1 mit ebenfalls handelsüblichen N,N-di(acyloxy-2-ethyl)-N-hydroxy-2-ethyl-N-methyl- ammoniummethosulfaten (Noxamium 91, Noxamium 920 oder Noxamium 960) umgesetzt. Es sind ebenfalls Produkte der Firma CECA ATO. Die Reaktion erfolgt durch kontinuierliche, portionenweise Zugabe des Noxamiums zur kräftig bewegten 70 bis 80°C warmen Aufschlämmung des durch Sedimentation vorgereinigten Clarsols. Nach kurzer Zeit scheidet sich feinteiliger, weißer Organobentonit ab. Nach wenigen Minuten wird das Produkt durch Zentrifugieren von der Mutterlauge getrennt und auf der Zentrifuge mit vier Portionen heißem Wasser gewaschen. Nach dem Trocknen im Warmluftstrom von maximal 60°C wird in der Schlagmühle zerkleinert und in der Kugelmühle fein gemahlen und durch das Sieb DIN 100 klassiert. Man erhält so ein wenig polares, chloridfreies Thixotropierungs- und Verdickungsmittel, welches in allen interessierenden Bereiche wie Bautechnik, Farben-Lacken- Beschichtungen-Kitten, Kosmetik, Pharmazie, Medizin usw. eingesetzt werden kann.Commercially available bentonite from CECA ATO (commercial products with the name "Clarsol") is, in accordance with its practical exchange capacity in mmol / 100 g in a molar ratio of 1: 1, also with commercially available N, N-di (acyloxy-2-ethyl) -N-hydroxy- 2-ethyl-N-methylammonium methosulfates (Noxamium 91, Noxamium 920 or Noxamium 960) implemented. They are also products from the company CECA ATO. The reaction is carried out by continuous, portionwise addition of the noxamium to the vigorously agitated 70 to 80 ° C warm slurry of the clarsol pre-cleaned by sedimentation. After a short time, finely divided, white organobentonite separates out. After a few minutes, the product is separated from the mother liquor by centrifugation and washed on the centrifuge with four portions of hot water. After drying in a warm air stream of max. 60 ° C, crushing is carried out and finely ground in the ball mill and classified by the DIN 100 sieve. This gives a slightly polar, chloride-free thixotropic and thickening agent, which is used in all areas of interest such as construction technology, paint and varnish. Coatings-Kitten, cosmetics, pharmacy, medicine etc. can be used.
Noxamium 91 und Noxamium 920 enthalten als Acylgruppen überwiegend die Fettsäuren von filtriertem Talg. Noxamium 960 enthält überwiegend die Fettsäuren des Palmöls. Die biologische Abbaubarkeit der Produkte erfüllt die Bedingungen der Methode NF-T 90306 oder den Direktiven OECD 301 B.Noxamium 91 and Noxamium 920 mainly contain the fatty acids of filtered sebum as acyl groups. Noxamium 960 mainly contains the fatty acids of palm oil. The biodegradability of the products fulfills the conditions of the NF-T 90306 method or the OECD 301 B directives.
Die Handelsprodukte Noxamium 91, 920 und 960 enthalten gewisse Mengen 2-Propanol. Es ist möglich, dieses 2-Propanol vorher beispielsweise durch Destillation zu entfernen. Die oben beschriebene Reaktion verläuft dennoch in gleicher Weise. Man erhält so völlig 2- propanolfreie Endprodukte.The commercial products Noxamium 91, 920 and 960 contain certain amounts of 2-propanol. It is possible to remove this 2-propanol beforehand, for example by distillation. The reaction described above is still the same. Completely 2-propanol-free end products are thus obtained.
Beispiel 2Example 2
Die Ausgangsmaterialien des Beispiels 1, nämlich Noxamium 91, 920 oder 960 und Bentonit, der jedoch nur durch Mahlen und Windsichten vorgereinigt ist, werden zusammen mit der Suspension einer Farbe, enthaltend Lösungsmittel, Pigmente und gegebenenfalls sonstige Zusätze, intensiv gemischt. Dabei bildet sich der Organobentonit und thixotropiert die Gesamtmischung. Um das dabei auch ebenfalls gebildete Alkalimethosulfat zu neutralisieren, kann gewünschtenfalls als Zusatz feinteiliges Calciumcarbonat verwendet werden. Man erhält so eine chloridfreie thixotropierte Farbe, die gewünschtenfalls durch weiteres Lösungsmittel auf die gewünschte Viskosität eingestellt wird. The starting materials of Example 1, namely noxamium 91, 920 or 960 and bentonite, which, however, is only pre-cleaned by grinding and air classifying, are mixed intensively together with the suspension of a paint containing solvents, pigments and optionally other additives. The organobentonite forms and thixotropes the entire mixture. In order to neutralize the alkali methosulfate, which is also formed, finely divided calcium carbonate can be used if desired. This gives a chloride-free thixotropic color which, if desired, is adjusted to the desired viscosity by means of a further solvent.

Claims

Patentansprüche claims
1. Hydrophobe, rheologisch wirksame Mittel auf Basis von ionenaustauschfähigen Tonen und/oder Tonmineralien, dadurch gekennzeichnet, daß sie als hydrophobierende Kationen N,N- di(acyloxy-2-ethyl)-N-hydroxy-2-ethyl-N-methylammoniummetho- sulfate, -methophosphate und/oder -dimethophosphate enthalten.1. Hydrophobic, rheologically active agents based on ion-exchangeable clays and / or clay minerals, characterized in that they are hydrophobic cations N, N- di (acyloxy-2-ethyl) -N-hydroxy-2-ethyl-N-methylammoniummetho- contain sulfates, methophosphates and / or dimethophosphates.
2. Hydrophobe, rheologisch wirksame Mittel gemäß Anspruch 1, dadurch gekennzeichnet, daß die Acylgruppen überwiegend aus gesättigten und/oder ungesättigten Fettsäuren mit 8 bis 22, vorzugsweise 16 bis 18 Kohlenstoffatomen, aus tierischem und/oder pflanzlichem und/oder synthetischem Ursprung bestehen.2. Hydrophobic, rheologically active agent according to claim 1, characterized in that the acyl groups consist predominantly of saturated and / or unsaturated fatty acids having 8 to 22, preferably 16 to 18 carbon atoms, of animal and / or vegetable and / or synthetic origin.
3. Hydrophobe, rheologisch wirksame Mittel gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, daß die ionenaustauschfähigen Tone und/oder Tonmineralien überwiegend Montmorillonite, Hectorite und/oder Attapulgite sind.3. Hydrophobic, rheologically active agents according to claim 1 or 2, characterized in that the ion-exchangeable clays and / or clay minerals are predominantly montmorillonites, hectorites and / or attapulgites.
4. Verfahren zur Herstellung von hydrophoben, rheologisch wirksamen Mitteln durch Umsetzung von ionenaustauschfähigen Tonen und/oder Tonmineralien mit hydrophobierenden Kationen, dadurch gekennzeichnet, daß die Tone und/oder Tonmineralien mit N,N-di(acyloxy-2-ethyl)-N-hydroxy-2-ethyl-N-methylammonium- methosulfaten, -methophosphaten und/oder -dimethophosphaten im Molverhältnis 1 : 1 bis 1 :0,1 umgesetzt werden. Verwendung von ionenaustauschfähigen Tonen und/oder Tonmineralien, die mit N,N-di(acyloxy-2-ethyl)-N-hydroxy-2-ethyl-N- methylammoniummethosulfaten, -methophosphaten und/oder -di- methophosphaten, hydrophobiert sind, als rheologisch wirksame Mittel in technischen, kosmetischen und medizinisch-pharmazeutischen Produkten. 4. A process for the preparation of hydrophobic, rheologically active agents by reacting ion-exchangeable clays and / or clay minerals with hydrophobic cations, characterized in that the clays and / or clay minerals with N, N-di (acyloxy-2-ethyl) -N- Hydroxy-2-ethyl-N-methylammonium methosulfates, methophosphates and / or dimethophosphates are reacted in a molar ratio of 1: 1 to 1: 0.1. Use of ion-exchangeable clays and / or clay minerals which are hydrophobized with N, N-di (acyloxy-2-ethyl) -N-hydroxy-2-ethyl-N-methylammonium methosulfates, -methophosphates and / or -dimethophosphates, as rheologically active agents in technical, cosmetic and medical-pharmaceutical products.
EP00912474A 1999-02-25 2000-02-17 Hydrophobic, rheologically active agent, method for producing the same and use thereof Withdrawn EP1156780A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE1999108006 DE19908006C1 (en) 1999-02-25 1999-02-25 New clay derivatives hydrophobilized with N,N-di(2-acyloxyethyl)-N-(2-hydroxyethyl)-N-methylammonium methylsulfates, useful as thixotropizing agents in technical, cosmetic and pharmaceutical products
DE19908006 1999-02-25
DE19946027 1999-09-25
DE19946027 1999-09-25
PCT/EP2000/001294 WO2000050003A1 (en) 1999-02-25 2000-02-17 Hydrophobic, rheologically active agent, method for producing the same and use thereof

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EP1156780A1 true EP1156780A1 (en) 2001-11-28

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AU (1) AU3423200A (en)
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Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4402881A (en) * 1980-11-12 1983-09-06 International Minerals & Chem. Corp. Method of making organophilic clays
JPH02139480A (en) * 1988-11-21 1990-05-29 Kao Corp Softening finishing agent
NL8901240A (en) * 1989-05-18 1990-12-17 Pelt & Hooykaas PROCESS FOR IMMOBILIZING ENVIRONMENTALLY HARMFUL METALS AND ORGANIC SUBSTANCES.
DE19602856A1 (en) * 1996-01-26 1997-07-31 Henkel Kgaa Biodegradable ester quats as flotation aids
DE19732015C1 (en) * 1997-07-25 1998-07-23 Henkel Kgaa Self-emulsifying formulation useful in production of cosmetics, e.g. hair conditions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0050003A1 *

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WO2000050003A1 (en) 2000-08-31

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