EP0000933A1 - Mousses de polyuréthanes hydrophobes, procédé pour leur préparation et leur application dans l'absorption d'huiles et de composés hydrophobes contenant éventuellement de l'halogène flottant sur l'eau - Google Patents

Mousses de polyuréthanes hydrophobes, procédé pour leur préparation et leur application dans l'absorption d'huiles et de composés hydrophobes contenant éventuellement de l'halogène flottant sur l'eau Download PDF

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Publication number
EP0000933A1
EP0000933A1 EP78100702A EP78100702A EP0000933A1 EP 0000933 A1 EP0000933 A1 EP 0000933A1 EP 78100702 A EP78100702 A EP 78100702A EP 78100702 A EP78100702 A EP 78100702A EP 0000933 A1 EP0000933 A1 EP 0000933A1
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EP
European Patent Office
Prior art keywords
polyurethane foams
hydrophobic
water
compounds
oil
Prior art date
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Granted
Application number
EP78100702A
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German (de)
English (en)
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EP0000933B1 (fr
Inventor
Wolfgang Dr. Jarre
Rolf Dr. Wurmb
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/0014—Use of organic additives
    • C08J9/0028—Use of organic additives containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/68—Treatment of water, waste water, or sewage by addition of specified substances, e.g. trace elements, for ameliorating potable water
    • C02F1/681—Treatment of water, waste water, or sewage by addition of specified substances, e.g. trace elements, for ameliorating potable water by addition of solid materials for removing an oily layer on water
    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/281—Monocarboxylic acid compounds
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
    • C08G18/3825—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing amide groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/0014—Use of organic additives
    • C08J9/0023—Use of organic additives containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0041—Foam properties having specified density
    • C08G2110/005—< 50kg/m3
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0083—Foam properties prepared using water as the sole blowing agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S521/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S521/905—Hydrophilic or hydrophobic cellular product

Definitions

  • the invention relates to polyurethane foams having densities of from 8 to '25 g / liter, the hydrophobic virtue of their nature and their content of closed and open cells especially for the absorption of oil and optionally halogen-containing hydrophobic compounds in water are suitable.
  • polyurethane foams from polyisocyanates, polyhydroxy compounds, optionally chain extenders, auxiliaries and additives is known from numerous patent and literature publications. For example, we would like to refer to the monographs by J.H. Saunders and K.C. Frisch, High Polymers, Volume XVI "Polyurethanes” Parts I and II (Interscience Publishers, New York) and R. Vieweg and A. Höchtlen, Plastics Manual, Volume VII, Polyurethane, Carl Hanser Verlag, Kunststoff.
  • open-cell foams made of polyurethanes, urea-formaldehyde condensates, polystyrene, cellulose acetate and others for oil absorption from water surfaces.
  • No. 3,779,908 a dispersion of crude oil in water is allowed to flow through a flexible, open-cell foam for oil absorption.
  • Oleophilic semi-hard to hard foams are further distributed according to US Pat. No. 3,886,067 on oil-containing water surfaces and, after oil absorption on the foam, collected and removed again.
  • the object of the present invention was to develop polyurethane foams which do not have these disadvantages.
  • the polyurethane foams should be quickly produced on site from polyurethane systems that are space-saving in liquid form and therefore inexpensive to transport.
  • polyurethane foams are particularly suitable for absorbing oil and halogen-containing hydrophobic solvents from water if they are hydrophobic and at the same time have closed and open cells in certain proportions.
  • the present invention thus relates to hydrophobic polyurethane foams, which are characterized in that they have a density of 8 to 25 g / liter, preferably 10 to 20 g / liter, and the number of closed cells 3 to 30%, preferably 10 to 20% and the open cells 97 to 70%, preferably 90 to 80%, based on the total number of cells.
  • hydrophobic polyurethane foams according to the invention are made both from the prepolymer process and preferably from the one-shot process from organic polyisocyanates, polyhydroxy compounds, blowing agents, catalysts, optionally chain extenders, auxiliaries and additives with the additional use of lipophilic compounds, preferably based on fatty acids and / or Fatty acid derivatives, advantageously produced on site.
  • Linear and / or branched hydroxyl-containing polyethers having molecular weights of about 300 to about 10,000, preferably from about 1,000 to about 6,000 and hydroxyl numbers from about 700 to about 20, preferably from 200 to 40, are expediently used as the polyhydroxy compounds.
  • the hydroxyl-containing polyethers are prepared by reacting one or more, optionally substituted, alkylene oxides having 2 to 4 carbon atoms in the alkylene radical with a starter molecule which contains at least two active hydrogen atoms bonded.
  • alkylene oxides are: tetrahydrofuran, 1,2- and 2,3-butylene oxide and preferably Propylene oxide. Mixtures of propylene oxide and ethylene oxide with an ethylene oxide content preferably less than 20% by weight, based on the total weight of the mixture, can also be used.
  • the alkylene oxides can be used individually, alternately in succession or as mixtures.
  • starter molecules are: water, aliphatic and aromatic dicarboxylic acids, such as adipic acid and terephthalic acid, and preferably dihydric and polyhydric alcohols, such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1-hexanediol , 6, glycerin, trimethylolpropane, 2,4,6-hexanetriol, pentaerythritol, sorbitol and sucrose.
  • dihydric and polyhydric alcohols such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1-hexanediol , 6, glycerin, trimethylolpropane, 2,4,6-hexanetriol, pentaerythritol, sorbitol and sucrose.
  • the preferred polyhydroxy compounds are di- and trifunctional hydroxyl-containing polypropylene oxides with molecular weights of 2,000 to. 6,000 used.
  • Suitable lipophilic compounds are, for example, optionally substituted, saturated and / or unsaturated aliphatic fatty acids with 10 to 25, preferably 12 to 20 carbon atoms in the molecule and their derivatives, preferably their esters with 2 to 20 carbon atoms in the alcohol radical and amides. Lipophilic fatty acid esters and amides which contain isocyanate-reactive groups and are thus incorporated into the polyurethane foam structure are particularly preferred.
  • Examples include: fatty acids such as capric, lauric, myristic, palmitic, stearic, arachinic, lignoceric, palmitic, oleic, ricinoleic, linoleic and linolenic acid; Fatty acid esters, such as castor oil, tall oil and adducts from the fatty acids mentioned and propylene and / or ethylene oxide and fatty acid amides, such as oleic acid mono- and diethanolamide, ricinoleic mono- and diethanolamide and their N, N-dialkylamides, such as ricinoleic acid dimethylaminopropylamide.
  • fatty acids such as capric, lauric, myristic, palmitic, stearic, arachinic, lignoceric, palmitic, oleic, ricinoleic, linoleic and linolenic acid
  • Fatty acid esters such as castor oil, tall oil and
  • the above-mentioned polyhydroxy compounds and lipophilic compounds are used in molar proportions of 1: 3 to 1:20, preferably from 1: 6 to. 1:15 and in particular about 1:10.
  • chain extenders in addition to the higher molecular weight polyhydroxy compounds.
  • the chain extenders have molecular weights less than 300, preferably from 80 to 200, and preferably have two active hydrogen atoms.
  • the polyurethane foams according to the invention are preferably produced without the use of chain extenders.
  • Water is used as the blowing agent, which reacts with isocyanate groups to form carbon dioxide. If the hydrophobic polyurethane foams according to the invention are produced by the prepolymer process, it has proven to be advantageous to foam the prepolymer having NCO end groups under water, that is to say in the presence of a large excess of water.
  • the quantitative ratio of water molecule to NCO group of the prepolymer can accordingly be as large as desired, but the value should not be less than about 5: 1. For example, molar ratios of water to NCO group in the prepolymer from 8: 1 to 1,000: 1 and larger have proven successful.
  • hydrophobic polyurethane foams according to the invention are produced by the one-shot process, it may be advantageous, depending on the type of polyhydroxy compounds and lipophilic compounds used, to mix the water used as blowing agent with a solubilizer.
  • Suitable solubilizers are all organic solvents with boiling points of 20 ° to 110 ° C., preferably 30 ° to 70 ° C., which are infinitely miscible with water and inert to isocyanate groups under the reaction conditions. Examples include acetone, methyl ethyl ketone, dioxane and tetrahydrofuran; acetone is preferably used.
  • the water is mixed with the solubilizer in such amounts that the weight ratio of water to solubilizer is 1: 1 to 10: 1, preferably 2: 1 to 4: 1.
  • the polyurethane foams according to the invention can be produced directly on site in the water. In these cases it has proven advantageous to accelerate the reaction between the polyhydroxy compounds, the water, optionally chain extenders and the lipophilic compounds, provided that these Zerewitinoff contain active groups bound in the molecule, and the highly reactive catalysts known to the organic polyisocanates, for example tertiary ones Amines, such as dimethylbenzylamine, N-methyl- or N-ethylmorpholine, dimethylpiperazine, 1,2-dimethylimidazole, 1-azabicyclo- (3,3,0) -oetane and preferably triethylenediamine and metal salts, such as tin dioctoate, lead octoate and tin diethylhexoate and preferably tin (II) salts and dibutyltin dilaurate and preferably mixtures of tertiary amines and organic tin salts.
  • Amines such as dimethylbenzyl
  • the amount to be used is determined empirically.
  • Polyurethane foams according to the invention by the one-shot process produced locally the catalysts must and quantities selected so that the start times at reaction temperatures of 0 ° to 35 0 C for about 2 to 10 S e-customer, preferably 2 to 5 Seconds.
  • the start time (cream time) is to be understood here as the time of the trouble-free pourability of the foamable mixture, ie the time available from mixing to the start of a visible reaction, in which mixing of the starting materials, discharge from the mixing element and spraying of the reaction mass is carried out Need to become.
  • polyurethane block foams are produced from the starting components mentioned above using conventional catalysts for the production of block foam, which as such are spread out on the oil-containing water surface, can be collected and pressed out after the absorption of oil, or can be comminuted and used as filler material for absorption columns can.
  • Auxiliaries and additives can also be incorporated into the reaction mixture. Examples include stabilizers, hydrolysis protection agents, pore regulators and surface-active substances.
  • surface-active substances are considered which serve to support the homogenization of the starting materials and, if appropriate, are also suitable for regulating the cell structure of the foams.
  • examples include siloxane-oxyalklene copolymers and other organopolysiloxanes, oxyethylated alkylphenols, oxyethylated fatty alcohols, paraffin oils, castor oil or castor oil esters and Vietnamese red oil, in quantities of 0.2 to 6 parts by weight per 100 parts by weight of polyisocyanate are used.
  • the polyurethane foams according to the invention can be produced by the prepolymer and preferably by the one-shot process.
  • a mixture of polybydroxy compound, lipophilic compound, water and optionally chain extender with the organic polyisocyanate is usually used in the presence of auxiliaries and additives at temperatures from 0 to 35 ° C., preferably 15 ° to 25 ° C implemented in such amounts that the ratio of Zerewitinoff active hydrogen atoms of the polyhydroxy compounds, lipophilic compounds and optionally chain extenders to the NCO group of the polyisocyanate is 0.7 to 1.3: 1, preferably about 1: 1 and the ratio all Zerewitinoff active hydrogen atoms - bonded to polyhydroxy compound, lipophilic compound, optionally chain extender and water to the NCO group of the polyisocyanate is approximately 1.3 to 5: 1, preferably 1.5 to 3: 1.
  • the starting components can be fed individually and mixed intensively in the mixing chamber.
  • catalysts, auxiliaries and additive fen to component A and to use the organic polyisocyanates as component B.
  • auxiliaries and additive fen to component A and to use the organic polyisocyanates as component B.
  • hydrophobic polyurethane foams according to the invention on water and the separation of those containing oil and / or halogen; Polyurethane foams impregnated with hydrophobic solvents from the water surface are made using known devices which are expediently installed on ships or in aircraft.
  • the prepolymers containing NCO groups are advantageously atomized under water.
  • the solvent By varying the solvent, the sinking, climbing or floating behavior can be varied within certain limits via the density of the prepolymer solution.
  • Suitable solvents are preferably those. which are readily miscible with the prepolymers containing NCO groups and the oil to be absorbed. Mention may be made, for example, of methylene chloride, toluene, cyclohexane, hexane and others.
  • the time of the conversion to polyurethanes can be influenced by the choice of catalyst.
  • the foamable prepolymer mixture is expanded with simultaneous foaming due to the carbon dioxide formed during the reaction of the prepolymers containing NCO groups with water.
  • the expanding and already expanded material rises to the water surface and absorbs the overlying oil or solvent layer from below.
  • the polyurethanes impregnated with oil and optionally halogen-containing, hydrophobic solvents can then be removed from the water using known methods surface to be separated.
  • the prepolymers containing NCO groups the polyisocyanates and mixtures of polyhydroxy compounds and lipophilic compounds already mentioned are reacted in the presence of any auxiliaries and additives in amounts such that the ratio of NCO groups to total hydroxyl of the mixture is 50: 1 to 2: 1, preferably 15: 1 to 5: 1.
  • the hydrophobic polyurethane foams according to the invention have a high absorption capacity for oil, for example crude, heating and diesel oil, and for optionally halogen-containing hydrophobic compounds, for example solvents such as hexane, benzene, toluene, Aniline, chloroform, carbon tetrachloride, dichloroethane and hexachlorocyclopentadiene.
  • oil for example crude, heating and diesel oil
  • halogen-containing hydrophobic compounds for example solvents such as hexane, benzene, toluene, Aniline, chloroform, carbon tetrachloride, dichloroethane and hexachlorocyclopentadiene.
  • the prepolymer solution containing NCO groups is then atomized under water.
  • the specific weight of the prepolymer containing NCO groups is 1.3546 g / cm 3 without solvent.
  • the density of the prepolymer solution can be varied from 0.922 to 1.333 g / cm 3 by mixing the prepolymer with organic solvents.
  • the tests show the very high oil absorption capacity of the foams according to the invention in comparison to conventional rigid and flexible foams.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Emergency Medicine (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
EP78100702A 1977-08-25 1978-08-18 Mousses de polyuréthanes hydrophobes, procédé pour leur préparation et leur application dans l'absorption d'huiles et de composés hydrophobes contenant éventuellement de l'halogène flottant sur l'eau Expired EP0000933B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772738268 DE2738268A1 (de) 1977-08-25 1977-08-25 Hydrophobe polyurethanschaumstoffe zur oelabsorption
DE2738268 1977-08-25

Publications (2)

Publication Number Publication Date
EP0000933A1 true EP0000933A1 (fr) 1979-03-07
EP0000933B1 EP0000933B1 (fr) 1983-03-30

Family

ID=6017233

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100702A Expired EP0000933B1 (fr) 1977-08-25 1978-08-18 Mousses de polyuréthanes hydrophobes, procédé pour leur préparation et leur application dans l'absorption d'huiles et de composés hydrophobes contenant éventuellement de l'halogène flottant sur l'eau

Country Status (4)

Country Link
US (1) US4237237A (fr)
EP (1) EP0000933B1 (fr)
JP (1) JPS5450099A (fr)
DE (2) DE2738268A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0013412A2 (fr) * 1979-01-15 1980-07-23 BASF Aktiengesellschaft Procédé pour la séparation de liquides organiques hydrophobes de l'eau
EP0044566A2 (fr) * 1980-07-23 1982-01-27 Champion International Corporation Dispositif et procédé pour la séparation de solides en suspension d'un courant
US4522953A (en) * 1981-03-11 1985-06-11 Lever Brothers Company Low density porous cross-linked polymeric materials and their preparation and use as carriers for included liquids
EP0714929A1 (fr) * 1994-11-30 1996-06-05 Inoac Corporation Mousse plastique imperméable à l'eau
GB2324798A (en) * 1997-05-01 1998-11-04 Ici Plc Open-celled cellular polyurethane products
WO1999005066A1 (fr) * 1997-07-23 1999-02-04 Huntsman Ici Chemicals Llc Mousse pour absorption de liquides hydrophobes
US6353037B1 (en) 2000-07-12 2002-03-05 3M Innovative Properties Company Foams containing functionalized metal oxide nanoparticles and methods of making same
US6495611B1 (en) 1999-06-23 2002-12-17 Basf Aktiengesellschaft Polyisocyanate polyaddition products
US6573305B1 (en) 1999-09-17 2003-06-03 3M Innovative Properties Company Foams made by photopolymerization of emulsions
DE102009000578A1 (de) * 2009-02-03 2010-08-12 Alexander Noskow Polyurethansorbens zur Entfernung von Kohlenwasserstoffen und Verfahren zur Reinigung von mit Kohlenwasserstoffen verunreinigten wässrigen Umgebungen und festen Oberflächen, welches das Polyurethansorbens verwendet

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Publication number Priority date Publication date Assignee Title
US4764282A (en) * 1986-09-26 1988-08-16 The Uniroyal Goodrich Tire Company Disposal of toxic and polymeric wastes
DE3711416A1 (de) * 1987-04-04 1988-05-19 Stuermer & Schuele Ohg Verfahren zur reinigung von wasser und vorrichtung dafuer
DE3718856A1 (de) * 1987-06-05 1988-12-22 Heinz Schnieders Wasser-aufbereitungsanlage fuer mit umweltschaedlichen, organischen substanzen, wie z.b. chlorierten kohlenwasserstoffen, verunreinigtes wasser
US4929359A (en) * 1988-01-26 1990-05-29 The United States Of America As Represented By The United States Department Of Energy Treatment of concentrated industrial wastewaters originating from oil shale and the like by electrolysis polyurethane foam interaction
US5074709A (en) * 1990-01-29 1991-12-24 Stensland Gary E Device and method for containing fluid spills
US5114272A (en) * 1990-07-02 1992-05-19 Brunhoff Frederic P Detachable boom and method for its use
US5248436A (en) * 1991-02-25 1993-09-28 Kovaletz Mark P Method for dispensing a fluidic media for treatment of waterborne spilled petroleum
EP0561760B1 (fr) * 1992-03-20 1998-08-26 Monsanto Company Extraction de composés organiques de solutions aqueuses
US5507949A (en) * 1992-03-20 1996-04-16 Monsanto Company Supported liquid membrane and separation process employing same
US6764603B2 (en) 1992-08-07 2004-07-20 Akzo Nobel Nv Material for extracting hydrophobic components dissolved in water
CA2103742C (fr) * 1992-08-11 2001-07-17 Robert Ziolkowski Greenley Polymere polyamphiphile solide utile dans un procede de separation
US6100363A (en) * 1998-03-13 2000-08-08 Basf Corporation Energy absorbing elastomers
US6747068B2 (en) 2001-02-15 2004-06-08 Wm. T. Burnett & Co. Hydrophobic polyurethane foam
US20030013777A1 (en) * 2001-05-01 2003-01-16 James Thornsberry Closed-cell thermosetting plastic foams & methods of producing thereof using acetone and water as blowing agents
US7138436B2 (en) 2001-06-13 2006-11-21 3M Innovative Properties Company Uncrosslinked foams made from emulsions
US7169318B1 (en) * 2003-03-18 2007-01-30 Hall Richard H Imbibed organic liquids, especially halogenated organics
DE102004013827A1 (de) * 2004-03-16 2005-10-06 Bulling, Walter Verfahren zum Herstellen eines Elementes aus weichelastischem PU-Schaumkunststoff und danach hergestelltes Element
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US4237237A (en) 1980-12-02
EP0000933B1 (fr) 1983-03-30
DE2738268A1 (de) 1979-03-08
DE2862213D1 (en) 1983-05-05
JPS5450099A (en) 1979-04-19

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