EP0214542B1 - Systèmes épaississants pour fluides fonctionnels contenant une quantité élevée d'eau et fluides fonctionnels contenant une quantité élevée d'eau comprenant ces systèmes - Google Patents
Systèmes épaississants pour fluides fonctionnels contenant une quantité élevée d'eau et fluides fonctionnels contenant une quantité élevée d'eau comprenant ces systèmes Download PDFInfo
- Publication number
- EP0214542B1 EP0214542B1 EP86111729A EP86111729A EP0214542B1 EP 0214542 B1 EP0214542 B1 EP 0214542B1 EP 86111729 A EP86111729 A EP 86111729A EP 86111729 A EP86111729 A EP 86111729A EP 0214542 B1 EP0214542 B1 EP 0214542B1
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- European Patent Office
- Prior art keywords
- water
- weight
- combinations
- mol
- functional fluids
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- Expired - Lifetime
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M173/00—Lubricating compositions containing more than 10% water
- C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
- C10M149/18—Polyamides
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/043—Mannich bases
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/044—Polyamides
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/045—Polyureas; Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/043—Ammonium or amine salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/01—Emulsions, colloids, or micelles
Definitions
- the invention relates to the use of combinations of special polymeric thickeners and surfactants as thickener systems for highly water-containing functional liquids.
- functional fluids are understood to mean hydraulic fluids, metalworking fluids (cooling lubricants) and metal hardening media.
- functional liquids are referred to as "highly water-containing", the water content of which is either more than 90% by weight, if no low-molecular glycols are used, or more than 70% by weight, preferably more than 80% by weight. -%, for the case that in addition to the water as a diluent, larger proportions of low molecular weight glycols, such as ethylene glycol, diethylene glycol, propylene glycol or dipropylene glycol, are used.
- the invention therefore relates to the use of combinations of water-soluble polymeric polyether polyols in which at least 50% of the hydroxyl end groups are blocked by reaction with a monoisocyanate having a C 12 -C 30 -alkyl or C 12 -C 30 -alkylene radical, and anionic and / or nonionic surfactants as thickener systems for highly water-containing functional liquids.
- the invention further relates to highly water-containing functional liquids containing, in addition to water, combinations of water-soluble polymeric polyether polyols in which at least 50% of the hydroxyl end groups by reaction with a monoisocyanate having a C 12 -C 31 alkyl or C 12 -C 30 alkylene radical are capped, and anionic and / or nonionic surfactants and optionally lubricity improvers, metal deactivators, corrosion inhibitors, defoamers, substances for adjusting or buffering certain pH values, anti-aging agents, biocides, colorants and / or glycols.
- the surfactants are contained in an amount such that 0.1 to 3 parts by weight, preferably 0.25, of polyether polyol capped to 1 part by weight up to 2.5 parts by weight of surfactant are eliminated.
- Nonionic and anionic surfactants are used as surfactants.
- Nonionic or anionic surfactants with a low tendency to foam are preferred. Both individual surfactants and mixtures of different surfactants can be used.
- anionic and nonionic surfactants which can be used in the combinations to be used according to the invention are e.g. in the review "Tenside”, by K. Kosswig in Ullmann's encyclopedia of techn. Chemistry, 4th ed., Volume 22, pages 468-494 and 498.
- the anionic surfactants are carboxylates, for example carboxymethylated oxethylates and derivatives of amino acids; Sulfonates, for example alkylbenzenesulfonates, alkylnaphthalenesulfonates, alkanesulfonates, ⁇ -olefinsulfonates, ⁇ -sulfofatty acid esters, sulfosuccinic acid esters, alkoxy, acyloxy and acylaminoalkanesulfonates; as sulfates, for example alkyl sulfates and ether sulfates, phosphonates and phosphates.
- carboxylates for example carboxymethylated oxethylates and derivatives of amino acids
- Sulfonates for example alkylbenzenesulfonates, alkylnaphthalenesulfonates, alkanesulfonates, ⁇ -olefinsulfonates, ⁇
- Alkanesulfonates be preferably having 8 to 30 carbon atoms, phenols, alkyl sulfosuccinic acid esters of ethoxylated with 8 to 30 moles of ethylene oxide C, 2-C, e fatty alcohols, of reacted with 8 to 70 moles of ethylene oxide C s -C 2o, from 8 to 30 moles of ethylene oxide ethoxylated C 12 -C 18 fatty acids or C 12 -C 18 fatty alcohols; C 12 -C 18 n-alkyl sulfates; Sulphates of C 12 ⁇ C 18 fatty alcohols, C 12 ⁇ C 18 fatty acids and Cg-C20 alkylphenols ethoxylated with 8 to 30 moles of ethylene oxide.
- Suitable nonionic surfactants are oxethylates, terminally blocked oxyethylates and fatty acid esters of polyhydroxy compounds, and also block polymers of propylene oxide and ethylene oxide.
- Reacted as nonionic surfactants with 8 to 50 moles of ethylene oxide are preferably C 12 -C 18 fatty acids, with 8 to 40 moles of ethylene oxide, ethoxylated C 12 -C 18 fatty acid amides with 8 to 30 moles of ethylene oxide, ethoxylated C 12 -C 18 fatty alcohols, Cg-C 20 alkylphenols ethoxylated with 8 to 50 moles of ethylene oxide and styrene or benzylated phenols ethoxylated with 8 to 60 moles of ethylene oxide.
- Nonionic surfactants with an HLB value ⁇ 18 are preferably used.
- the monoisocyanate-capped water-soluble polymeric polyether polyols to be used in the combinations to be used according to the invention are reaction products of known polymeric water-soluble polyether polyols which have an average molecular weight of 5,000 to 70,000 (determined by determining the OH end groups; the number of OH end groups becomes average molecular weight calculated using the following formula: have, with a C 12 -C 30 alkyl or C 12 -C 30 alkylene having monoisocyanate.
- the C 12 -C 30 alkyl radicals are, in particular, the dodecyl, hexadecyl, octadecyl and the behenyl radical, and the C 12 -C 30 alkylene radical in particular the oleyl radical.
- These aliphatic hydrocarbon radicals do not necessarily have to be bonded directly to the isocyanate group, but can also be bonded to the isocyanate group via other groups, for example aromatic rings and / or urethane groups.
- Such monoisocyanates in which the long-chain aliphatic hydrocarbon radicals are not directly bound to the isocyanate group are, for example, the addition products from 1 mol of a C 12 -C 30 -n-alkanol, for example lauryl, myristyl, cetyl, stearyl or behenyl alcohol or of oleyl alcohol to 1 mole of an aliphatic, cycloaliphatic, aromatic or heterocyclic diisocyanate.
- the amount of monoisocyanate is such that at least 50%, preferably 70 to 100%, particularly preferably 85 to 100% of the hydroxyl end groups present in the water-soluble polymeric polyether polyols are capped.
- the capping of the OH end groups of the polymeric water-soluble polyether polyols with the monoisocyanates having a C 12 -C 30 alkyl or C 12 ⁇ C 30 alkylene radical is a reaction which is known in principle (see, for example, Ullmann's Enzyklopadie der techn. Chemie, 4th ed ., Volume 19, pages 309-310).
- the end of the reaction can be determined by IR spectroscopy on the basis of the disappearance of the absorption band typical of isocyanates at about 2,270 cm -1 . determine.
- This addition reaction can be accelerated in a known manner by using known catalysts.
- the water-soluble polymeric, optionally urethane or ester group-containing polyether polyols of average molecular weight 5,000 to 70,000 on which the blocked water-soluble polyether polyols are based are known or can be obtained by processes known per se, for example by polymerizing ethylene oxide or copolymerizing ethylene oxide with other alkylene oxides in the presence of compounds, which have at least two active hydrogen atoms, and optionally modifying the water-soluble polymeric polyether polyols thus obtained by reaction with diisocyanates or dicarboxylic acids to give water-soluble urethane or ester groups polymeric polyether polyols or by polymerizing ethylene oxide or copolymerizing ethylene oxide and other alkylene oxides in the presence of compounds which have two active hydrogen atoms and reacting the water-soluble polyether diols obtained with polyisocyanates, while maintaining a ratio of isocyanate groups / OH groups of at most 0.5 : 1, to water-soluble polymeric polyether polyol
- the combinations of special monoisocyanate-capped water-soluble polymeric polyether polyols and anionic and / or nonionic surfactants to be used according to the invention are produced by mixing both components together in a liquid state to form a homogeneous liquid. Since they are often solid at room temperature, the components are generally heated to the melting temperature, ie temperatures from 60 to 100 ° C., and stirred at this temperature until a homogeneous liquid has formed. When using surfactant mixtures, it may be advantageous to first mix only one surfactant with the masked polyether polyol in the liquid state and then to stir the second or the remaining surfactants into the homogeneous melt.
- the combinations of special capped water-soluble polymeric polyether polyols and anionic and / or nonionic surfactants obtained in this way are diluted by adding water to liquid concentrates, the water content of which is about 30 to 70% by weight, preferably 40 to, for better manageability in the preparation of the functional liquids 60% by weight, based on the weight of the concentrate.
- the ready-to-use hydraulic fluids, metalworking fluids (cooling lubricants) and metal hardening media are produced from these concentrates by further dilution with water.
- the concentrates, or the functional liquids prepared from them by dilution can also contain additives which are usually used in these functional liquids. These are lubricity improvers, metal deactivators, corrosion inhibitors, defoamers, substances for adjusting or buffering certain pH values, anti-aging agents, biocides, identification dyes in the usual amounts for these additives, as well as monomeric and / or oligomeric glycols.
- the highly water-containing functional liquids which are thickened according to the invention preferably contain 3 to 7% by weight of the combination to be used according to the invention as a thickener system and optionally additionally 0.5 to 3, preferably 1 to 3% by weight % of the above-mentioned additives commonly used in functional liquids, and optionally up to 25% by weight, for example 0.5 to 20% by weight of monomeric and / or oligomeric glycols.
- a mixture of 1346.4 g of polyether polyol A (0.06 mol), 0.15 g of 1,4-diazabicycio-2,2,2-octane (DABCO) and 500 g of dry dioxane is heated to the reflux temperature with stirring.
- 50.6 g of dodecyl isocyanate (0.24 mol) are added dropwise within one hour.
- the reaction mixture is then stirred at the reflux temperature until no isocyanate band can be detected in the infrared spectrum of a reaction mixture sample.
- the dioxane has been distilled off at about 130 ° C./15 hPa, a reaction product which is viscous at elevated temperatures and solidifies at low temperatures remains.
- Masked polyether polyol 12 (not according to the invention, comparative compound):
- the polyether chain contains 25% by weight propylene oxide and 75% by weight ethylene oxide units in a statistical distribution. Average molecular weight: 22,400.
- Reaction product of pentaerythritol, ethylene oxide and propylene oxide The polyether chains contain 25% by weight of propylene oxide and 75% by weight of ethylene oxide units in a statistical distribution. Average molecular weight: 15,500.
- Polyethylene glycol with an average molecular weight of 5555 is Polyethylene glycol with an average molecular weight of 5555.
- capped polyether polyol and surfactant given in the table below are liquefied by heating to about 90 ° C. and stirred into a homogeneous liquid. This is then diluted by adding water to a concentrate containing 50% by weight of water.
- the amount of capped polyether polyol given in the table is first liquefied with only one of the surfactants to be used in the amount given for this surfactant in the table by heating to about 90 ° C. and stirred into a homogeneous liquid.
- the other or the other surfactants in the amount specified for this or these surfactants in the table are then also stirred into this at an elevated temperature until a homogeneous liquid has also formed again. This is again diluted by adding water to a concentrate containing 50% by weight of water.
- the concentrates obtained according to a) or b) are diluted to 100 parts by weight of solution with stirring by adding further water.
- a mixture of 80% by weight of water, 10% by weight of diethylene glycol and 10% by weight of dipropylene glycol is diluted to 100 parts by weight of solution.
- the water content of which, depending on the amount of thickener system used, is from 91 to 95.5% by weight the viscosities at 40 and 50 ° C. and the change in viscosity are reduced Influence of shear forces (according to DIN 51 382; modification: 300 cycles instead of 30 cycles) determined.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Lubricants (AREA)
Claims (7)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE19853531915 DE3531915A1 (de) | 1985-09-07 | 1985-09-07 | Verdickungssysteme fuer hoch wasserhaltige funktionelle fluessigkeiten und die diese verdickungssysteme enthaltenden hoch wasserhaltigen funktionellen fluessigkeiten |
DE3531915 | 1985-09-07 |
Publications (3)
Publication Number | Publication Date |
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EP0214542A2 EP0214542A2 (fr) | 1987-03-18 |
EP0214542A3 EP0214542A3 (en) | 1989-05-10 |
EP0214542B1 true EP0214542B1 (fr) | 1990-10-31 |
Family
ID=6280325
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86111729A Expired - Lifetime EP0214542B1 (fr) | 1985-09-07 | 1986-08-25 | Systèmes épaississants pour fluides fonctionnels contenant une quantité élevée d'eau et fluides fonctionnels contenant une quantité élevée d'eau comprenant ces systèmes |
Country Status (6)
Country | Link |
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US (1) | US4770804A (fr) |
EP (1) | EP0214542B1 (fr) |
JP (1) | JPS6259696A (fr) |
BR (1) | BR8604275A (fr) |
CA (1) | CA1288413C (fr) |
DE (2) | DE3531915A1 (fr) |
Families Citing this family (15)
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DE3905939A1 (de) * | 1989-02-25 | 1990-08-30 | Huels Chemische Werke Ag | Tensidkombination |
GB9003192D0 (en) * | 1990-02-13 | 1990-04-11 | Du Pont | Improvements in or relating to polymeric compounds |
US5141662A (en) * | 1990-02-15 | 1992-08-25 | Dexheimer Edward M | Heat transfer fluids comprising oxyalkylenated polyols |
DE4017688A1 (de) * | 1990-06-01 | 1991-12-05 | Bayer Ag | Verbesserte funktionelle fluessigkeiten und neue polyoxyalkylenpolymere |
DE4017687A1 (de) * | 1990-06-01 | 1991-12-05 | Bayer Ag | Verbesserte funktionelle fluessigkeiten |
JPH0776695A (ja) * | 1993-09-07 | 1995-03-20 | Sanyo Chem Ind Ltd | 水−グリコール型作動液 |
JP3581450B2 (ja) * | 1995-09-01 | 2004-10-27 | 旭電化工業株式会社 | エマルション塗料組成物 |
WO1997021743A1 (fr) * | 1995-12-08 | 1997-06-19 | Henkel Corporation | Epaississants polymeres pour compositions aqueuses |
US6107394A (en) * | 1995-12-08 | 2000-08-22 | Henkel Corporation | Polymeric thickeners for aqueous compositions |
JP2000094951A (ja) * | 1998-09-02 | 2000-04-04 | Webasto Thermosyst Internatl Gmbh | 濃化された氷貯蔵媒体を有する氷貯蔵要素 |
GB0027216D0 (en) * | 2000-11-08 | 2000-12-27 | Avecia Ltd | Polyether/polyurethane association thickeners |
JP5089179B2 (ja) * | 2007-01-19 | 2012-12-05 | Jx日鉱日石エネルギー株式会社 | 極微量油剤供給式切削・研削加工方法 |
DE102007056532A1 (de) * | 2007-11-23 | 2009-05-28 | Clariant International Ltd. | Mischungen von phosphorhaltigen Verbindungen, ein Verfahren zu deren Herstellung und deren Verwendung als Flammschutzmittel |
JP6892100B2 (ja) | 2016-12-27 | 2021-06-18 | 出光興産株式会社 | 水系焼入れ液組成物及びそれを用いた金属材料の製造方法 |
JP6355033B1 (ja) * | 2017-08-22 | 2018-07-11 | 大同化学工業株式会社 | 水溶性熱処理剤組成物 |
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DE1495749C3 (de) * | 1963-10-12 | 1974-09-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung wasserlöslicher bzw. in Wasser quellbarer oberflächenaktiver Umsetzungsprodukte aus Polyäthylenglykoläthern und Isocyanaten |
US3813341A (en) * | 1970-03-09 | 1974-05-28 | Buemah Oil Trading Ltd | Derivatives of glycols,glycol ethers and glycol esters |
GB1439741A (en) * | 1974-01-31 | 1976-06-16 | Air Prod & Chem | Copolyers of polyfunctional polyether polyols and cyclic nitrogen ous and ester monomers |
US4257902A (en) * | 1976-08-04 | 1981-03-24 | Singer & Hersch Industrial Development (Pty.) Ltd. | Water-based industrial fluids |
US4180491A (en) * | 1976-12-01 | 1979-12-25 | Rohm And Haas Company | Nonionic polyurethane thickener with surfactant cothickener and organic diluent, clear concentrates, aqueous print pastes, coloring compositions, methods of making and printing |
JPS5641300A (en) * | 1979-09-12 | 1981-04-17 | Asahi Denka Kogyo Kk | Aqueous hydraulic fluid |
US4354956A (en) * | 1979-10-22 | 1982-10-19 | Basf Wyandotte Corporation | Thickening aqueous systems with alpha-olefin oxide-modified liquid polyether thickeners |
US4428860A (en) * | 1979-10-22 | 1984-01-31 | Basf Wyandotte Corporation | Polyether thickeners for aqueous systems containing additives for increased thickening efficiency |
US4395351A (en) * | 1979-10-22 | 1983-07-26 | Camp Ronald L | Polyether-based thickeners with additives for increased efficiency in aqueous systems |
CA1163041A (fr) * | 1979-10-22 | 1984-02-28 | Assadullah Nassry | Fluide hydraulique epaissi par synergie, utilisant des polyethers modifies par un oxyde-olefinique |
US4312775A (en) * | 1979-10-22 | 1982-01-26 | Basf Wyandotte Corporation | Polyether thickeners for aqueous systems containing additives for increased thickening efficiency |
US4312768A (en) * | 1979-10-22 | 1982-01-26 | Basf Wyandotte Corporation | Synergistic polyether thickeners for water-based hydraulic fluids |
US4288639A (en) * | 1979-10-22 | 1981-09-08 | Basf Wyandotte Corporation | Alpha-olefin oxide-modified liquid polyether thickeners |
US4310436A (en) * | 1979-10-22 | 1982-01-12 | Basf Wyandotte | Polyether-based thickeners with additives for increased efficiency in aqueous systems |
US4411819A (en) * | 1979-10-22 | 1983-10-25 | Basf Wyandotte Corporation | Thickening aqueous compositions with polyethers modified with alpha-olefin oxides |
CA1177988A (fr) * | 1979-12-26 | 1984-11-13 | Robert J. Knopf | Obtention de copolymeres sequences de polyether- urethane, liquides et de viscosite elevee |
US4481367A (en) * | 1979-12-26 | 1984-11-06 | Union Carbide Corporation | High viscosity polyoxyalkylene glycol block copolymers and method of making the same |
US4390439A (en) * | 1981-03-30 | 1983-06-28 | Basf Wyandotte Corporation | Water-based hydraulic fluids having improved lubricity and corrosion inhibiting properties employing neodecanoic acid |
AU548443B2 (en) * | 1981-04-01 | 1985-12-12 | Basf Wyandotte Corp. | Polyether thickener |
GR76105B (fr) * | 1981-04-01 | 1984-08-03 | Basf Wyandotte Corp | |
US4390440A (en) * | 1981-06-08 | 1983-06-28 | Basf Wyandotte Corporation | Thickened water-based hydraulic fluids |
DE3302465C2 (de) * | 1982-03-03 | 1984-10-11 | Akzo Gmbh, 5600 Wuppertal | Verdickungsmittel auf der Basis Polyätherderivate |
US4481125A (en) * | 1982-05-03 | 1984-11-06 | E.F. Houghton & Co. | Water-based hydraulic fluid |
EP0116564A1 (fr) * | 1982-07-08 | 1984-08-29 | E.F. HOUGHTON & Co. | Epaississants polyethers pour fluides hydrauliques a base d'eau |
US4491526A (en) * | 1983-04-04 | 1985-01-01 | Basf Wyandotte Corporation | Thickened, water-based hydraulic fluid with reduced dependence of viscosity on temperature |
US4499233A (en) * | 1983-05-03 | 1985-02-12 | Nl Industries, Inc. | Water dispersible, modified polyurethane and a thickened aqueous composition containing it |
US4636326A (en) * | 1984-12-12 | 1987-01-13 | S. C. Johnson & Son, Inc. | Thickener compositions for water-based hydraulic and metalworking fluid compositions |
-
1985
- 1985-09-07 DE DE19853531915 patent/DE3531915A1/de not_active Withdrawn
-
1986
- 1986-08-25 EP EP86111729A patent/EP0214542B1/fr not_active Expired - Lifetime
- 1986-08-25 DE DE8686111729T patent/DE3675302D1/de not_active Expired - Lifetime
- 1986-08-25 US US06/900,064 patent/US4770804A/en not_active Expired - Fee Related
- 1986-09-01 JP JP61203894A patent/JPS6259696A/ja active Pending
- 1986-09-05 BR BR8604275A patent/BR8604275A/pt unknown
- 1986-09-05 CA CA000517526A patent/CA1288413C/fr not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP0214542A3 (en) | 1989-05-10 |
DE3675302D1 (de) | 1990-12-06 |
DE3531915A1 (de) | 1987-03-19 |
CA1288413C (fr) | 1991-09-03 |
BR8604275A (pt) | 1987-05-05 |
JPS6259696A (ja) | 1987-03-16 |
US4770804A (en) | 1988-09-13 |
EP0214542A2 (fr) | 1987-03-18 |
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