WO2003029338A1 - Composes a base de polyorganosiloxanes, procedes de production et utilisation desdits composes - Google Patents

Composes a base de polyorganosiloxanes, procedes de production et utilisation desdits composes Download PDF

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Publication number
WO2003029338A1
WO2003029338A1 PCT/EP2002/010641 EP0210641W WO03029338A1 WO 2003029338 A1 WO2003029338 A1 WO 2003029338A1 EP 0210641 W EP0210641 W EP 0210641W WO 03029338 A1 WO03029338 A1 WO 03029338A1
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weight
composition
silica
parts
alkali metal
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PCT/EP2002/010641
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German (de)
English (en)
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John Huggins
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Ge Bayer Silicones Gmbh & Co. Kg
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Publication of WO2003029338A1 publication Critical patent/WO2003029338A1/fr

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    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D19/00—Degasification of liquids
    • B01D19/02—Foam dispersion or prevention
    • B01D19/04—Foam dispersion or prevention by addition of chemical substances
    • B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D19/00—Degasification of liquids
    • B01D19/02—Foam dispersion or prevention
    • B01D19/04—Foam dispersion or prevention by addition of chemical substances
    • B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
    • B01D19/0409—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance compounds containing Si-atoms
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • 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
    • C08K5/54—Silicon-containing compounds

Definitions

  • the invention relates to compositions based on polyorganosiloxanes which contain pyrogenic silicas, a process for their preparation, emulsions and solid compositions thereof and the use thereof as defoamer preparations.
  • problems with increased levels of foaming occur, e.g. B. in the gassing of waste water with air, in the intensive stirring of liquids, in the production of pulp and paper, and in the washing or dyeing of textiles.
  • Foaming in these systems can often be effectively reduced by adding small amounts of defoaming agents.
  • Defoamers based on polydimethylsiloxanes have proven themselves particularly in strongly alkaline systems as well as at higher temperatures.
  • defoamers based on polysiloxanes can be increased significantly by means of hydrophobic solids, in particular hydrophobic silicas.
  • This type of defoamer preparation usually contains 0.5 to 30% hydrophobic silica, preferably 3 to 10% hydrophobic silica.
  • the effectiveness of the defoamer preparations is improved by distributing the silica in the polysiloxane as homogeneously as possible.
  • the polysiloxane can be partially replaced by other water-insoluble liquids, e.g. from the group of mineral oils or fatty acid esters.
  • preparations can also contain siloxane copolymers with polyglycols. These defoamer preparations are mainly used as aqueous emulsions because of their improved handling and meterability.
  • Defoamer preparations based on polysiloxanes and commercially available, hydrophobic silicas are also generally known. Defoamer preparations can be prepared from polysiloxanes with hydrophilic or partially hydrophobic silicas, the silicas being rendered hydrophobic in situ by reaction with the polysiloxane or an added hydrophobizing agent. From DE 12 39 276 it is known that a mixture of Polydimethylsiloxane with silica heated for several hours at temperatures from 100 ° C to 200 ° C. However, this process is slow and not very effective. US 3,235,509 discloses that polydimethylsiloxanes and silicas react in the presence of catalytic amounts of different acids at elevated temperatures.
  • the object of the invention is achieved by a composition based on polyorganosiloxanes, obtainable by reacting
  • compositions have a low viscosity with good storage stability and a high defoamer activity, especially at high silica contents.
  • compositions of the invention based on polysiloxanes and pyrogenic silicas, the addition of organic fatty acids in the in situ hydrophobization fills to a significantly lower viscosity.
  • fatty acids only have an influence on the viscosity together with pyrogenic silicas, but not with precipitated silicas.
  • the fatty acids also increase the viscosity stability of the resulting preparations and also their effectiveness as defoamers.
  • the compositions of the invention have as component (a) polyorganosiloxanes.
  • polyorganosiloxanes are understood to mean all polyorganosiloxanes.
  • the inventive composition based on polyorganosiloxanes is obtained by reacting
  • the polyorganosiloxanes (a) used according to the invention include both linear and branched polyorganosiloxanes or mixtures of various linear and / or branched polyorganosiloxanes.
  • Conventional (to C 25 ) saturated, (C to C 5 ) unsaturated or aromatic hydrocarbon radicals can be present as the organic group on the silicon.
  • saturated unbranched or branched hydrocarbon radicals examples of the unbranched hydrocarbons are methyl, ethyl, propyl, n-butyl, n-hexyl, n-octyl, n-decyl and n-dodecyl.
  • branched hydrocarbons examples include isopropyl, isobutyl, isopentyl and neopentyl.
  • Unbranched hydrocarbons from the group of methyl, ethyl, propyl, n-butyl, n-pentyl and n-hexyl are preferably used.
  • unsaturated hydrocarbon radicals examples include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, decenyl or dodecenyl. Vinyl is preferably used for the unsaturated hydrocarbon radicals.
  • aromatic hydrocarbons are exemplified by phenyl groups or naphthyl groups.
  • the groups which contain phenyl radicals are preferred.
  • the methyl group is preferred.
  • Trimethylsiloxy-terminated polydimethylsiloxanes are particularly preferred. It is generally known that polydimethylsiloxanes can contain small amounts of hydroxyl, alkoxy, acyloxy and aryloxy groups as well as monoorganosiloxane groups.
  • the viscosity of the polyorganosiloxanes or polysiloxane mixtures used is advantageously in the range between 50 and 3,000,000 Pa.s at 25 ° C, preferably at 50 and 100,000 mPa.s at 25 ° C.
  • the compositions of the invention have "pyrogenic silicas" as component (b).
  • the pyrogenic silicic acid is produced by flame hydrolysis. Corresponding ones are commercially available, for example, as Aerosil®, HDK® and Cab-O-Sil®.
  • hydrophilic, partially hydrophobicized and hydrophobic silicas which expediently have a BET surface area of at least 50-400 m 2 / g, preferably partially hydrophobicized and hydrophobicized pyrogenic silicas with at least 90 m Ig BET surface area.
  • partially hydrophobic silicas should be understood to mean those silicas which have already been partially treated by a hydrophobizing agent and which, according to IR determination, still have free SiOH groups. They have according to their treatment with methylsilanes, methylsiloxanes or hydrocarbons, which is typical in most cases, such as. B. at Aerosil®, R972, R 976, Wacker HDK H20, H30, Cab-O-Sil TS 720 of TS 610 a carbon content of 1-3% by weight and are no longer wettable with water without additives. Depending on the degree of hydrophobization, wettability can only be increased by the addition of e.g. Alcohols to water are achieved, evaluation method e.g. Methanol number.
  • the more completely hydrophobicized, water-non-wettable silicas such as Aerosil®812, HDK H 2000, Cab-O-Sil TS 530 accordingly have higher carbon contents of 1.5-7% by weight.
  • the SiOH groups have been reduced to the detection limit.
  • the amount of the necessary hydrophobicizing agent d) is reduced by the proportion of the amount of siloxane equivalent to the carbon content.
  • the amount of pyrogenic silica in the compositions according to the invention is in the range from 0.5 to 15% by weight, based on the total amount of components a) to d).
  • the silica content is set as high as possible within the limits specified.
  • the preferred silica content is on average in the range between 3 to 12% by weight, and particularly preferably in the range between 4 to 7.5% by weight.
  • the compositions of the invention have as component (c) “C 4 to C 3 o carboxylic acids”.
  • the C 4 to C 3 o-carboxylic acids are taken to mean all organic acids of the general structure
  • R represents a C 3 to C 29 organic radical.
  • the organic radical can be both saturated and unsaturated, aromatic, halogen-containing, hydroxy, ether or
  • Unbranched or branched, saturated or unsaturated (C 8 to C 22 ) carboxylic acids such as octanoic acid, dodecanoic acid, oleic acid,
  • Ricinoleic acid linolenic acid, stearic acid and mixtures thereof.
  • compositions of the invention have at least one “hydrophobizing agent” as component (d).
  • hydrophobizing agents are understood to mean all known organosilanes, organosiloxanes, organosilazanes and polyorganosiloxanes which react with the SiOH groups on the surface of the silica to form organosiloxane groups
  • Known hydrophobizing agents of this type are, for example, those selected from the group consisting of an organosilane, an organosiloxane, an organosilazane and a polyorganosiloxane, each of which contains at least one reactive hydroxyl, alkoxy, acyloxy, chlorine, Imino and / or amino group, for example silazanes such as hexamethyldisilazane and organochlorosilanes such as dimethyldichlorosilane, trimethylmonochlorosilane,
  • Octyltrichlorosilane or the like can be called.
  • Silazanes and hydroxyl-containing siloxanes and polysiloxanes, such as trimethylsilanol, hexamethyldisilazane, and ⁇ -hydroxy-terminated polyorganosiloxanes are preferred.
  • ⁇ , ⁇ -Hydroxy-terminated polyorganosiloxanes with viscosities between 20 and 1000 mPa.s at 25 ° C. and a content of SiOH groups between 0.5 to 25% by weight are particularly preferred.
  • Catalysts used according to the invention are all known acidic and basic substances which accelerate a reaction of the hydrophobizing agent (d) with the SiOH or Si-O-Si groups of the silica (b).
  • Basic catalysts as disclosed in US Pat. No. 3,560,401, are particularly preferred.
  • catalysts such as alkali metal and alkaline earth metal oxides, hydroxides, alkoxides, aryloxides and silanoates, Tetraalkylammonium hydroxides, alkoxides and silanolates, tetraalkylphosphonium hydroxides, alkoxides and silanolates, triarkylhydrazinium hydroxides, alkoxides and silanolates,
  • Trialkyl guanidine hydroxides, alkoxides and silanolates, and monoalkyl, dialkyl and trialkyl amines include sodium, potassium, magnesium, calcium, strontium and cesium hydroxides, sodium, potassium, magnesium, calcium and cesium oxides, sodium, potassium, magnesium, calcium and cesium methoxides , ethoxides, phenoxides, and -butoxide, sodium, potassium, magnesium, calcium and cesium salts of methylsilanetriol, dimethylsilanediol, and Phenylsilantriol, tetramethylammonium hydroxide, tetraethylammonium hydroxide, Phenyltrimemylammoniumhydroxid, Triethyloctadecylammoriiumhydroxid, Benzyltrimemylammoniumhydroxid, Cyclohexyltoibutylarnmoniurnhydroxid, Vinyltrimethylammoniumhydr
  • the catalyst is an alkali metal hydroxide, an alkali metal siloxanoate, an alkali metal alkoxide, a quaternary ammonium hydroxide or its siloxanoate.
  • catalysts based on alkali metal hydroxides, such as sodium, potassium and cesium hydroxide, and their siloxanoates and reaction products with polyorganosiloxanes are particularly preferred.
  • the preferred amount of carboxylic acid, hydrophobizing agent and the catalyst in the defoamer preparation according to the invention or the process for producing the defoamer preparation according to the invention depends on the properties of the silica, its surface, its amount and the conditions during the preparation of the preparation. The areas of use of the defoamer preparation can also determine the optimal amounts of silica.
  • the amount of carboxylic acid for an optimal effect is between 1 and 50% by weight of the amount of silica. Amounts of carboxylic acid between 5 and 20% by weight of the amount of silica are preferred.
  • the amount of water repellent depends on the content of silica, its surface, the chemical structure and reactivity of the water repellent. As a rule, amounts in the range from 10 to 100% by weight of the amount of silica are used.
  • the catalyst content corresponds to the desired reactivity. At lower temperatures, more catalyst is required than with the preparations at higher temperatures. Catalysts are preferred in an amount in the range between 0.0001 to 2% by weight, preferably 0.02 to 0.2% by weight, of the amount of polyorganosiloxane a) used.
  • Another object of the present invention is a process for the preparation of compositions based on polysiloxanes, wherein
  • a) 0.5 to 15 parts by weight of at least one pyrogenic silica are mechanically dispersed in 62.5 to 99.245 parts by weight of at least one polyorganosiloxane,
  • Parts by weight of at least one organosiloxane-containing water repellent is reacted at temperatures between 50 and 300 ° C.
  • Another object of the present invention is a further method for producing compositions based on polysiloxanes, wherein
  • the processes according to the invention are carried out at temperatures from 50 to 300.degree. Temperatures between 100 to 200 ° C. are preferred. The preferred temperature is mainly determined by the rate of reaction of the hydrophobizing agent with the silica under the action of the catalyst.
  • compositions according to the invention thus obtained can be used directly as defoamer preparations.
  • compositions can also be previously heated from volatile components at elevated temperature and / or with vacuum and freed of volatile components. Temperatures between 100 and 300 ° C are preferred. Temperatures between 130 and 220 ° C. at a vacuum of less than 50 mbar are particularly preferred in order to remove the volatile constituents.
  • compositions according to the invention In the preparation of the compositions according to the invention, all known dispersing apparatuses such as planetary mixers, rudder, dissolver, colloid mills, stirrers with dissolver disks, rotor-stator homogenizers, high-pressure homogenizers or ultrasound can be used to disperse the silica. Several dispersing devices can also be used simultaneously or in succession.
  • compositions according to the invention can be used as defoamer preparations for combating foam directly without dilution.
  • the preparations can also be packaged in the form of a solution, a preferably aqueous emulsion, or a solid composition in which they are applied to a solid carrier material. These phrases are then easy to dose when using. Solutions in polyglycols or alcohols are preferred in the context of the invention.
  • Suitable carrier materials include, for example: starch, cellulose derivatives, zeolites and other silicates, polyethylene oxides and urea.
  • compositions according to the invention are contained in the abovementioned emulsions, solutions and solid compositions in amounts of 5 to 80% by weight.
  • Defoamer emulsions are prepared by known processes using emulsifiers.
  • emulsifiers from the group consisting of sorbitan esters, such as sorbitan oleates, sobitan stearates, polyethylene stearates, ethoxylated fatty alcohols, ethoxylated sorbitan esters and ethoxylated glycerol mono- and diesters, can be used.
  • admixtures of thickeners such as polyacrylic acid and cellulose esters and their salts or urethane polyether copolymers can also be used.
  • Defoamer emulsions can be produced, for example, in simple stirred tanks, optionally in combination with rotor-stator homogenizers, colloid mills or high-pressure homogenizers.
  • compositions or defoaming preparations according to the invention are particularly effective defoamers in various aqueous, foaming systems.
  • the defoamer effectiveness is often defined by the knock-down effect and persistence.
  • the knock-down effect is the property of the defoamer to effectively and quickly destroy foam that has already formed.
  • persistence is used to effectively combat foam over a longer period of time.
  • the defoamer preparations according to the invention have a long-lasting effectiveness, in particular at elevated temperature under strongly alkaline conditions. Defoamer preparations from the prior art which contain the same content of finely divided hydrophobic silica are significantly less effective under such conditions. Preparations with hydrophobic precipitated silicas not according to the invention are in particular of lower persistence.
  • compositions according to the invention have stable viscosities, in particular with a high content of finely divided silica.
  • the viscosity stability of the preparations according to the invention can be observed over a longer period.
  • the Viscosity of comparable preparations from the prior art with a proportion of more than 5% by weight of hydrophobic pyrogenic silica generally becomes significantly higher after a few days' storage and leads to gel-like substances. Such gel-like defoamer substances are difficult to handle and less effective in combating foam.
  • Aerosil® R 812 a pyrogenic hydrophobic silica with a BET surface area of 260 m 2 / g and a carbon content of 2.6%, were incorporated for 15 minutes at 500 rpm.
  • a very viscous mixture was created.
  • 4.5 g of oleic acid and 22.5 g of an ⁇ , ⁇ -hydroxypoly-dimethylsiloxane with an SiOH group content of about 20% and a viscosity of 20 mPa.s were added in succession. The mixture was then stirred at 150 ° C. and 500 rpm for 1 h, and then heated at 150 ° C. in vacuo (15 mbar) for 1 h. About 30 g of distillate was produced.
  • the product obtained was a slightly cloudy, homogeneous liquid with a viscosity of 20.8 Pa.s at 23 ° C. Even after three months of storage, the viscosity rose only slightly to 30.6 Pa.s - see Table 1.
  • Example 1 As in Example 1, 296 g of a trimethylsiloxy-terminated polydimethylsiloxane with a viscosity of about 9.6 Pa.s at 23 ° C., 500 ppm alkali metal catalyst and 22.5 g of a pyrogenic hydrophobic silica with a BET surface area of 260 m 2 / g and a carbon content of 2.6% as in Example 1 at 150 ° C mixed into a homogeneous solution. Then different amounts of oleic acid and ⁇ , ⁇ -hydroxypolydimethylsiloxane were added, the mixture was stirred at 150 ° C. for 1 hour and then heated at 150 ° C. in vacuo (15 mbar). The results were summarized in Table 1.
  • Example 6 The product from Examples 2-4 was in each case a slightly cloudy, homogeneous liquid, the viscosity of which barely changed after several months of storage.
  • the product from Comparative Example 5 was a cloudy, homogeneous mass which became gel-like after a few days and had a greatly increased viscosity (Table 1).
  • Example 6 The product from Examples 2-4 was in each case a slightly cloudy, homogeneous liquid, the viscosity of which barely changed after several months of storage.
  • the product from Comparative Example 5 was a cloudy, homogeneous mass which became gel-like after a few days and had a greatly increased viscosity (Table 1).
  • Example 6 Example 6
  • Example 2 As in Example 1, 300 g of a trimethylsiloxy-terminated polydimethylsiloxane solution with a viscosity of 9.3 Pa.s at 23 ° C. and 500 ppm alkali metal catalyst at 150 ° C. were mixed for 3 hours by stirring to give a homogeneous mixture. Then, 19.5 g of the fumed hydrophobic silica having a BET surface area of 260 m 2 / g and a carbon content of 2.6% of example 1 over about 15 minutes at 500 Umin "1 incorporated.
  • the product obtained was a slightly cloudy, homogeneous liquid with a viscosity of 23.2 Pa.s at 23 ° C. Even after storage for several months, the viscosity hardly changed (Tab. 1).
  • Example 6 was repeated, but without the addition of oleic acid. After heating, a cloudy, homogeneous liquid with a viscosity of 142 Pa.s. The product became gel-like after a short period of storage.
  • Example 2 As in Example 1, 300 g of a trimethylsiloxy-terminated polydimethylsiloxane with a viscosity of 10.2 Pa.s at 23 ° C and 500 ppm alkali metal catalyst at 150 ° C for 3 h were mixed to form a homogeneous solution. Then, 17.5 g of a fumed hydrophobic silica having a BET surface area of 260 m 2 / g and a carbon content of 2.6% of example 1 over about 60 minutes at 150 ° C and 1000 rpm "1 incorporated.
  • Example 2 As in Example 1, 300 g of a trimethylsiloxy-terminated polydimethylsiloxane with a viscosity of 9.3 Pa.s at 23 ° C and 500 ppm alkali metal catalyst at 150 ° C for 3 h were mixed to form a homogeneous solution. Then
  • the product obtained was a cloudy, homogeneous liquid with a viscosity of 102 Pa.s at 23 ° C. After 7 days the product became gel-like with an unmeasurable .0 viscosity (Tab. 1).
  • Example 9 was repeated, but deviating from it, in that after heating at 150 ° C., the product was cooled to 60 ° C. and mixed with 2.9 g of oleic acid for 30 minutes.
  • the product is a cloudy, homogeneous liquid with a viscosity of 67 Pa.s at 0 23 ° C. After 7 days the product became gel-like with an unmeasurable viscosity.
  • the product obtained was a slightly cloudy, homogeneous liquid with a viscosity of 3.6 Pa.s at 23 ° C (Tab. 1).
  • Omega.-hydroxypolydimethylsoxane with an SiOH group content of about 20% and a viscosity of 20 mPa.s were added in succession.
  • the mixture was then stirred at 160 ° C. for 1 h and then baked at 160 ° C. in vacuo (30 mbar) for 1 h.
  • About 3.2 kg of distillate was formed.
  • the product obtained was a slightly cloudy, homogeneous liquid with a viscosity of 25.0 Pa.s at 25 ° C. Even after three months of storage, the viscosity had only risen to 31.4 mPa.s (Tab. 1).
  • Example 13 As in Example 13, 30 kg of a trimethylsiloxy-terminated polydimethylsiloxane with a viscosity of 7.1 Pa.s at 23 ° C. were mixed with 500 ppm of alkali metal hydroxide catalyst at 160 ° C. for 3 hours by stirring to give a homogeneous solution. Then 1.95 kg of the pyrogenic, hydrophobic silica with a BET surface area of 260 m 2 / g and a carbon content of 2.6% from Example 1 were incorporated and homogeneously mixed for 1 hour.
  • the product obtained was a slightly cloudy, homogeneous liquid with a viscosity of 28.3 Pa.s at 23 ° C (Tab. 1). mixed with 500 ppm alkali metal hydroxide catalyst at 160 ° C for 3 h by stirring to a homogeneous solution. Then 2.25 kg of a hydrophilic precipitated silica Sipernat FK 383 with a BET surface area of 170 m 2 / g were incorporated and mixed homogeneously for 1 h.
  • Example 13 a defoamer emulsion consisting of 18 g of the product, 12 g of a polyether-siloxane copolymer with a viscosity of 5521 mPa.s, 13.8 g of sorbitan monooleate, 1.7 g of polyoxyethylene (20) sorbitan monooleate, became 0 , 2 g bioeid and 80 g water, containing 0.475% carboxymethyl cellulose as a thickener.
  • the emulsion had a viscosity of 1283 mPa.s at 23 ° C.
  • Example 13 In a foam test apparatus as in Example 13, after adding 0.3 g of defoamer emulsion, the foam was reduced to a height of only 3.5 cm after 10 s, but after 9 minutes of constant pumping, the foam height rose again to 14 cm.
  • the defoamer effect of this comparison emulsion is significantly less than for the emulsion from the defoamer preparation according to the invention in Examples 13 and 14.
  • Example 16 was repeated, except that oleic acid was not used. 'The mixture was then heated at 160 ° C and vacuum (30 mbar).

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Abstract

La présente invention concerne des composés à base de polyorganosiloxanes, obtenus par mise en réaction de a) 62,5 à 99,245 % en poids d'au moins un polyorganosiloxane, b) 0,5 à 15 % en poids d'au moins un acide silicique pyrogéné, c) 0,005 à 7,5 % en poids d'au moins un acide carboxylique (C4 à C30) et d) 0,25 à 15 % en poids d'au moins un produit imperméabilisant, ces proportions se rapportant chacune à la quantité totale des constituants a) à d), en présence d'au moins un catalyseur. Cette invention concerne également des procédés de production desdits composés, des émulsions aqueuses contenant ces composés, des compositions solides contenant lesdits composés ainsi que leur utilisation comme préparation antimousse.
PCT/EP2002/010641 2001-09-26 2002-09-23 Composes a base de polyorganosiloxanes, procedes de production et utilisation desdits composes WO2003029338A1 (fr)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009080428A1 (fr) * 2007-12-20 2009-07-02 Evonik Degussa Gmbh Préparation anti-mousse
US8022130B2 (en) 2003-12-01 2011-09-20 Evonik Degussa Gmbh Adhesive and sealant systems
CN107115694A (zh) * 2016-08-31 2017-09-01 江苏四新科技应用研究所股份有限公司 一种有机硅组合物及其制备、应用
WO2020108750A1 (fr) * 2018-11-28 2020-06-04 Wacker Chemie Ag Formulations antimousses contenant des organopolysiloxanes
CN114307260A (zh) * 2021-11-06 2022-04-12 南京瑞思化学技术有限公司 一种聚醚组合物的制备方法
EP2508237B1 (fr) 2011-04-07 2022-08-24 Shin-Etsu Chemical Co., Ltd. Composé d'huile et composition antimousse
US11925883B2 (en) 2018-11-28 2024-03-12 Wacker Chemie Ag Defoaming formulations containing organopolysiloxanes

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DE4118598A1 (de) * 1991-06-06 1992-12-10 Wacker Chemie Gmbh Unter abspaltung von alkoholen zu elastomeren vernetzbare organo(poly)siloxanmassen
JPH08151521A (ja) * 1994-09-29 1996-06-11 Toray Dow Corning Silicone Co Ltd 金型成形用シリコーンゴム組成物
WO2001052964A1 (fr) * 2000-01-18 2001-07-26 Ge Bayer Silicones Gmbh & Co. Kg Formulation et procede de production d'un compose reducteur de mousse

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Publication number Priority date Publication date Assignee Title
US4310444A (en) * 1979-09-14 1982-01-12 Toray Silicone Company, Ltd. Flame retardant silicone rubber compositions
DE4118598A1 (de) * 1991-06-06 1992-12-10 Wacker Chemie Gmbh Unter abspaltung von alkoholen zu elastomeren vernetzbare organo(poly)siloxanmassen
JPH08151521A (ja) * 1994-09-29 1996-06-11 Toray Dow Corning Silicone Co Ltd 金型成形用シリコーンゴム組成物
WO2001052964A1 (fr) * 2000-01-18 2001-07-26 Ge Bayer Silicones Gmbh & Co. Kg Formulation et procede de production d'un compose reducteur de mousse

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8022130B2 (en) 2003-12-01 2011-09-20 Evonik Degussa Gmbh Adhesive and sealant systems
WO2009080428A1 (fr) * 2007-12-20 2009-07-02 Evonik Degussa Gmbh Préparation anti-mousse
US8426478B2 (en) 2007-12-20 2013-04-23 Evonik Degussa Gmbh Defoamer formulation
EP2508237B1 (fr) 2011-04-07 2022-08-24 Shin-Etsu Chemical Co., Ltd. Composé d'huile et composition antimousse
CN107115694A (zh) * 2016-08-31 2017-09-01 江苏四新科技应用研究所股份有限公司 一种有机硅组合物及其制备、应用
CN107115694B (zh) * 2016-08-31 2019-11-08 江苏四新科技应用研究所股份有限公司 一种有机硅组合物及其制备、应用
WO2020108750A1 (fr) * 2018-11-28 2020-06-04 Wacker Chemie Ag Formulations antimousses contenant des organopolysiloxanes
US11925883B2 (en) 2018-11-28 2024-03-12 Wacker Chemie Ag Defoaming formulations containing organopolysiloxanes
US11931673B2 (en) 2018-11-28 2024-03-19 Wacker Chemie Ag Defoaming formulations containing organopolysiloxanes
CN114307260A (zh) * 2021-11-06 2022-04-12 南京瑞思化学技术有限公司 一种聚醚组合物的制备方法

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