WO2000014143A1 - Catalyseurs destines a produire des polyetherols par polymerisation par ouverture de noyau d'oxydes d'alkylene - Google Patents

Catalyseurs destines a produire des polyetherols par polymerisation par ouverture de noyau d'oxydes d'alkylene Download PDF

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Publication number
WO2000014143A1
WO2000014143A1 PCT/EP1999/006225 EP9906225W WO0014143A1 WO 2000014143 A1 WO2000014143 A1 WO 2000014143A1 EP 9906225 W EP9906225 W EP 9906225W WO 0014143 A1 WO0014143 A1 WO 0014143A1
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WO
WIPO (PCT)
Prior art keywords
compounds
catalysts
polyetherols
inorganic
ring
Prior art date
Application number
PCT/EP1999/006225
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German (de)
English (en)
Inventor
Georg Heinrich Grosch
Harald Larbig
Reinhard Lorenz
Dieter Junge
Kathrin Harre
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 WO2000014143A1 publication Critical patent/WO2000014143A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/007—Mixed salts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/20—Carbon compounds
    • B01J27/232—Carbonates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/20—Carbon compounds
    • B01J27/232—Carbonates
    • B01J27/236—Hydroxy carbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4866—Polyethers having a low unsaturation value
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • C08G65/2645—Metals or compounds thereof, e.g. salts
    • C08G65/2654—Aluminium or boron; Compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • C08G65/2645—Metals or compounds thereof, e.g. salts
    • C08G65/2654—Aluminium or boron; Compounds thereof
    • C08G65/2657—Aluminosilicates; Clays; Zeolites

Definitions

  • the invention relates to catalysts, their preparation and their use for the preparation of polyether alcohols.
  • Polyether alcohols also known as polyetherols, are important feedstocks in the production of polyurethanes. They are usually produced by catalytic addition of lower alkylene oxides, in particular ethylene oxide and / or propylene oxide, to H-functional starter substances. Usually soluble basic metal hydroxides or salts are used as catalysts, with potassium hydroxide having the greatest practical importance.
  • the polyether will propose in EP-A-268 922 to use cesium hydroxide as catalyst.
  • cesium hydroxides which dissolve in the polyether polyols, have the major disadvantage that they have to be extracted from the polyetherol with great effort after the synthesis and the resulting waste has to be disposed of.
  • DD-A-203 734 and DD-A-203 735 describe a process for the preparation of polyether alcohols using zinc hexacyanocobaltate.
  • the production of zinc hexacyanometalates is also known. It is usually carried out by reacting solutions of metal salts, mostly zinc chloride, with solutions of alkali metal or alkaline earth metal cyanometallates, such as potassium hexacyanocobaltate.
  • a water-miscible component containing one or more heteroatoms is normally added to the precipitation suspension formed immediately after the precipitation process. This component can already be present in one or in both educt solutions.
  • the water-miscible component containing heteroatoms can preferably be an ether, polyether, alcohol, ketone or a mixture of at least two of the compounds mentioned. Such methods are described, for example, in US Pat. No. 3,278,457, US Pat. No. 3,278,458, US Pat. No.
  • the object of the invention was therefore to provide catalysts for the ring-opening polymerization of alkylene oxides on H-functional starters which can be easily separated from the polyetherol and which, if appropriate, permit a continuous procedure in the synthesis of polyether alcohol.
  • the object could be achieved by applying sparingly soluble, catalytically active compounds on solid supports, in solid supports or shaping the sparingly soluble, catalytically active compounds into shaped bodies.
  • the term “sparingly soluble” means that the concentration of the metal ions which are present in the compounds used as catalysts in the starting, intermediate and end products of polyether alcohol synthesis is less than 50 ppm per type of metal ion.
  • the term “catalytically active” means that the compounds catalyze the ring-opening polymerization of alkylene oxides.
  • the invention accordingly relates to catalysts for the preparation of polyether alcohols by ring-opening polymerization of alkylene oxides, characterized in that one or more ⁇ / compounds of the general formula (I)
  • M ' is at least one metal ion selected from the group lithium, sodium, potassium, rubidium, cesium, magnesium, calcium, strontium, barium, nickel or zinc, and mixtures thereof,
  • M '' is at least one metal ion selected from Groups IIIA, IVA, IB to VIIIB and As, Sb and Bi, and mixtures thereof,
  • A is at least one monovalent or polyvalent, inorganic or organic anion
  • L is an inorganic or organic ligand
  • a is a rational number greater than zero
  • a, b, c, d, e and f are selected so that the electroneutrality of the compound is ensured
  • inert means that the materials used as carriers are inert in the reaction medium of the polyether alcohol synthesis.
  • the inert supports used according to the invention are macroscopic shaped bodies as are customary and known as catalyst supports, for example strands, grit, tablets, nets, packs, fabrics, fibers, spheres and the inner walls of reactors.
  • the macroscopic shaped bodies can consist of inorganic and / or organic materials.
  • Inorganic materials are, for example, oxides, carbides, nitrides or inert metals.
  • carbides are transition metal carbides, such as tungsten carbide, and silicon carbide or boron carbide.
  • Suitable nitrides are, for example, boron nitride, silicon nitride or aluminum nitride.
  • inert metals are steels, aluminum, precious metals, nickel, stainless steel, titanium, tantalum, kanthai.
  • Metal oxides which are inert under the reaction conditions mentioned can be used, in particular those of metals from groups IIA to IVA and IB to Vlllb, and also oxidic compounds which contain elements from groups IA to VIIA and / or the metals from groups Ib to Vlllb.
  • the catalysts according to the invention can be prepared by applying the compounds of the general formula (I) to the surface of the shaped support or by mixing compounds of the general formula (I) with an unformed support material and subsequent shaping. It is also possible to deform powdered compounds of the general formula (I) into unsupported catalysts.
  • these compounds can be made by coprecipitation.
  • the desired metal ions are placed in a common solution and precipitated by adding further reagents, for example by shifting the pH by adding a base.
  • the precipitated solids can also be subjected to a hydrothermal treatment for further crystallization.
  • An intimate mixing of the components by rotating the common solution in is also possible.
  • the materials thus produced can then be dried and calcined.
  • such compounds can be produced by impregnation or impregnation.
  • a solid which already contains at least one of the desired components is mixed with at least one solution which can contain the other metal ions.
  • a drying and / or calcining step can also be carried out.
  • the solids obtained in this way can then be subjected to further treatments by treating them with organic or inorganic ligands.
  • Preferred compounds of the general formula (I) are those which, as M ', preferably contain alkaline earth or zinc ions, optionally together with the other aforementioned metal ions.
  • the pure oxides and hydroxides such as magnesium oxide, calcium oxide, strontium oxide, barium oxide, zinc oxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide or zinc hydroxide are to be mentioned here as special compounds.
  • magnesium oxide, calcium oxide, strontium oxide, barium oxide, zinc oxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide or zinc hydroxide are to be mentioned here as special compounds.
  • Inorganic anions can be used as anions, for example halides, anions containing sulfur, phosphorus, nitrogen or carbon, and also organic anions such as alkoxides, carboxylates, amides, sulfides.
  • One method of applying the compounds of the general formula (I) to an inert shaped body is to spray on a suspension of these compounds in an inert liquid.
  • the spray suspension can either be the precipitation mash of the compounds or the already synthesized and possibly dried compound can be suspended in a suitable suspension liquid.
  • inorganic or organic substances which have a binding effect can also be added to the spray suspension.
  • the moldings produced in this way can then be subjected to a calcining step. This can have a positive effect on the adhesion to the molded body and can also promote the formation of the active phase.
  • reactive, inorganic or organic substances in pure form in the form of their solutions, dispersions or emulsions, which can react either thermally or photochemically, i.e. are crosslinked and thus enable the compound of the general formula (I) to be held firmly on the support.
  • Reactive organic polymers whose crosslinking products form porous structures are preferred.
  • the powder of these compounds can be applied directly to the shaped body analogously to a high-solids coating process - one of which is described in DE 4,44,23,46, among others .
  • the moldings are sprayed with an adhesion-promoting liquid parallel to the feed of the powder.
  • spraying it is possible to add substances to the adhesion-promoting liquid which, through their binding action, increase the adhesion of Ensure connection of the general formula (I) on the shaped body.
  • Synthesis of the compound or its precursor on the shaped body For this purpose, the various solutions containing the educts are brought into contact with the shaped body either at the same time or in a short time offset.
  • the shaped body can be brought into contact with the solutions by spraying, dipping, soaking, impregnating or similar procedures. Mixing the liquids on the shaped body can lead to precipitation of the compound of the general formula (I) or its precursor on the shaped body. It is also possible to apply the desired metal ions by successive soaking or impregnation.
  • the shaped bodies obtained in this way can, if necessary, also be subjected to hydrothermal crystallization. Furthermore, the shaped bodies obtained in this way can be subjected to a temperature step, if this should be necessary in order to first produce the compounds of the general formula (I).
  • substances that promote adhesion can be added before or after the temperature step.
  • the compounds of the general formula (I) are applied to inert moldings.
  • deformed compounds of the general formula (I) can also be prepared by making full contacts from the powders. This can be done by tableting, extruding or extruding. Depending on the level of the production costs for the compounds of the general formula (I), one will either choose to support them on inert shaped bodies or to deform them into full contacts.
  • additional lubricants These can be graphite, boron nitride or organic molecules such as stearates or alginates. A temperature step can follow the tabletting in order to burn out the organic tabletting aids again.
  • the powdery compounds of the general formula (I) are first mixed with a pasting liquid in a kneader, pan or similar device processed plastic mass.
  • a kneading step further ingredients can be added to the resulting mass, which either improve the properties of the plastic mass during the actual shaping step or give the shaped body produced from this mass better cohesion.
  • the contents of the additives are not critical, they should be so high that they have their full effect, but not so high that the catalytic activity of the catalysts is reduced.
  • Another possibility is to include a compound of general formula (I) in a solid matrix.
  • the solid matrix can be inorganic or organic in nature.
  • the compounds of the general formula (I) can be suspended in metal acid esters or alkoxymetalates.
  • the metal acid esters can be polymerized to solid substances.
  • the esters of silicon, aluminum, titanium and / or zirconic acid are preferred.
  • the polymerization should be carried out so that the resulting solid particles can be used in a fixed bed arrangement. Furthermore, the solid particles obtained should have sufficient porosity to enable the starting materials and products to be transported to and from the catalytically active centers. To improve the porosity, it is possible to add auxiliaries during the polymerization which are removed again after the polymerization by physical or chemical treatments.
  • the polymerization can also be carried out in such a way that an open-pore foam is formed in which the compound of the general formula (I) is fixed.
  • the catalysts described above are outstandingly suitable for the continuously operated polymerization of alkylene oxides to polyether polyols.
  • the catalyst can be in a fixed bed, floating bed or fluid bed.
  • the fixed bed or floating bed is preferred.
  • the polyether polyols are produced under the conditions customary for this purpose, namely at temperatures between 20 and 250 ° C and pressures between 0.10 to 100 bar, in particular 1 and 60 bar.
  • the removal of the supported or 5 shaped catalysts according to the invention from the finished polyether is very simple. In the fixed bed mode of operation, the previously required filtration step can be completely dispensed with. The catalytic activity of the catalysts is not impaired by the application to the supports or the shaping.
  • the strands are dried at 120 ° C and calcined at 500 ° C for 5 hours.
  • Example 5 200 g of powder from Example 2 are compacted with 52 ml of an aqueous formic acid solution (2% by weight of formic acid) for 45 hours in a kneader and shaped into round strands with a diameter of 2 mm. The strands are dried at 120 ° C.
  • Example 5 200 g of powder from Example 2 are compacted with 52 ml of an aqueous formic acid solution (2% by weight of formic acid) for 45 hours in a kneader and shaped into round strands with a diameter of 2 mm. The strands are dried at 120 ° C.
  • an aqueous formic acid solution 2% by weight of formic acid
  • magnesium hydroxide carbonate (4 MgC03 • Mg (OH) 2) are compacted with 33.3 g of boehmite (Pural® S3, from Condea) and 78 ml of an aqueous formic acid solution (2% by weight of formic acid) in a kneader and added Round strands with a 2 mm diameter deformed.
  • the strands are dried at 120 ° C and calcined at 500 ° C for 5 hours.
  • the synthesis was carried out in a cleaned and dried 5-1 stirred reactor. 779.5 g of glycerol and 35.3 g of split catalyst according to Example 1 were added to the reactor at room temperature. The contents of the vessel were then rendered inert by evacuating and filling the reactor three times with nitrogen. At 95 ° C, vacuum was less than 1 mbar abs for 5 hours. created. A total of 1648 g of propylene oxide were then added in portions at 125 ° C. in such a way that an internal reactor pressure of 7.2 bar abs. was not exceeded. After the end of the feed and reaction, a water jet vacuum was applied (at 125 ° C.) for 30 min.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyethers (AREA)

Abstract

L'invention concerne la production de polyétherols par polymérisation par ouverture de noyau d'oxydes d'alkylène. Cette invention est caractérisée en ce qu'au moins un composé de type (I) M'aM''b (OH)c Od * Ae * Lf est appliqué sur ou introduit dans des supports inertes fixes ou moulé en corps moulés, sachant que M' représente au moins un ion métallique choisi parmi les groupes IA, IIA et Ni ou Zn, et leurs mélanges, M'' représente au moins un ion métallique dans les groupes IIIA,IVA, IB à VIIIB, As, Sb et Bi, et leurs mélanges, A représente au moins un anion inorganique ou organique monovalent ou polyvalent, L représente un ligand inorganique ou organique, sachant que a est un nombre rationnel, b, c, d, e et f sont des nombres rationnels supérieurs ou égaux à zéro, c et d ne pouvant pas être simultanément égaux à zéro et a, b, c, d, e et f sont choisis de telle façon que l'électroneutralité de la liaison soit garantie.
PCT/EP1999/006225 1998-09-05 1999-08-25 Catalyseurs destines a produire des polyetherols par polymerisation par ouverture de noyau d'oxydes d'alkylene WO2000014143A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19840587.1 1998-09-05
DE19840587A DE19840587A1 (de) 1998-09-05 1998-09-05 Katalysatoren zur Herstellung von Polyetherolen durch ringöffnende Polymerisation von Alkylenoxiden

Publications (1)

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WO2000014143A1 true WO2000014143A1 (fr) 2000-03-16

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WO (1) WO2000014143A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008004343A1 (de) 2007-01-19 2008-07-24 Basf Se Verfahren zur Herstellung von Polyesteralkoholen
DE102008042715A1 (de) 2007-10-12 2009-04-16 Basf Se Polyetherpolyole
US7528288B2 (en) 2005-08-30 2009-05-05 Basf Aktiengesellschaft Method for production of polyether alcohols
US7750191B2 (en) 2004-06-30 2010-07-06 Basf Aktiengesellschaft Method for producing polyether alcohols
US9587788B2 (en) 2010-06-04 2017-03-07 Dow Global Technologies Llc Suspensions for enhanced oil recovery

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1336866A (en) * 1969-12-12 1973-11-14 Kyowa Chem Ind Co Ltd Composite metal hydroxides and process for their preparation
US4962237A (en) * 1985-12-13 1990-10-09 The Dow Chemical Company Catalytic process for the preparation of polyols
US5326891A (en) * 1990-10-29 1994-07-05 Henkel Kommanditgesellschaft Auf Aktien Hydrophobicized double layer hydroxide compounds
WO1994014700A1 (fr) * 1992-12-21 1994-07-07 Amoco Corporation Procede de preparation de gaz synthetique a l'aide de catalyseurs contenant du nickel
WO1996022161A1 (fr) * 1995-01-18 1996-07-25 Mannesmann Ag Catalyseur pour la deshydrogenation oxydante d'hydrocarbures paraffiniques et utilisation de ce catalyseur
WO1996023611A1 (fr) * 1995-01-30 1996-08-08 Aristech Chemical Corporation Liants basiques mineraux
DE19632440A1 (de) * 1996-08-12 1998-02-19 Basf Ag Verfahren zur Herstellung von aus Polykationen aufgebauten, geformten Mischhydroxiden
DE19734906A1 (de) * 1997-08-12 1999-02-18 Basf Ag Verfahren zur Alkoxylierung von Estern und Amiden

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1336866A (en) * 1969-12-12 1973-11-14 Kyowa Chem Ind Co Ltd Composite metal hydroxides and process for their preparation
US4962237A (en) * 1985-12-13 1990-10-09 The Dow Chemical Company Catalytic process for the preparation of polyols
US5326891A (en) * 1990-10-29 1994-07-05 Henkel Kommanditgesellschaft Auf Aktien Hydrophobicized double layer hydroxide compounds
WO1994014700A1 (fr) * 1992-12-21 1994-07-07 Amoco Corporation Procede de preparation de gaz synthetique a l'aide de catalyseurs contenant du nickel
WO1996022161A1 (fr) * 1995-01-18 1996-07-25 Mannesmann Ag Catalyseur pour la deshydrogenation oxydante d'hydrocarbures paraffiniques et utilisation de ce catalyseur
WO1996023611A1 (fr) * 1995-01-30 1996-08-08 Aristech Chemical Corporation Liants basiques mineraux
DE19632440A1 (de) * 1996-08-12 1998-02-19 Basf Ag Verfahren zur Herstellung von aus Polykationen aufgebauten, geformten Mischhydroxiden
DE19734906A1 (de) * 1997-08-12 1999-02-18 Basf Ag Verfahren zur Alkoxylierung von Estern und Amiden

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7750191B2 (en) 2004-06-30 2010-07-06 Basf Aktiengesellschaft Method for producing polyether alcohols
US7528288B2 (en) 2005-08-30 2009-05-05 Basf Aktiengesellschaft Method for production of polyether alcohols
DE102008004343A1 (de) 2007-01-19 2008-07-24 Basf Se Verfahren zur Herstellung von Polyesteralkoholen
DE102008042715A1 (de) 2007-10-12 2009-04-16 Basf Se Polyetherpolyole
US9587788B2 (en) 2010-06-04 2017-03-07 Dow Global Technologies Llc Suspensions for enhanced oil recovery
US10240079B2 (en) 2010-06-04 2019-03-26 Dow Global Technologies Llc Suspension for enhanced oil recovery

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