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WO2018147979A1 - Procédé de préparation de polyéthers de silicone - Google Patents

Procédé de préparation de polyéthers de silicone Download PDF

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Publication number
WO2018147979A1
WO2018147979A1 PCT/US2018/013958 US2018013958W WO2018147979A1 WO 2018147979 A1 WO2018147979 A1 WO 2018147979A1 US 2018013958 W US2018013958 W US 2018013958W WO 2018147979 A1 WO2018147979 A1 WO 2018147979A1
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WIPO (PCT)
Prior art keywords
polyether
organohydrogensiloxane
platinum
chch
sih
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PCT/US2018/013958
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English (en)
Inventor
Alix SCHMIDT
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Dow Silicones Corp
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Dow Silicones Corp
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Publication of WO2018147979A1 publication Critical patent/WO2018147979A1/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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen

Definitions

  • This invention relates to a process for the preparation of silicone polyethers.
  • the process is useful to prepare silicone polyethers of improved quality, and is particularly useful when employed in batch or continuous process to achieve residual silicon-hydride content specifications.
  • SPEs Silicone polyethers
  • surfactant applications such as in the production of polyurethane foams, and as ingredients in personal care products.
  • SPEs are typically based on copolymer structures of
  • silicone polyether block copolymers having pendant polyoxyalkylene groups.
  • the copolymer structures of silicone polyethers are the "rake” type, where a predominately linear polyorganosiloxane provides the "backbone” of the copolymer architecture with pendant polyoxyalkylene groups forming the "rake”.
  • "ABA" structures are also common, where a pendant polyoxyalkylene group is at each molecular terminal of a linear polyorganosiloxane.
  • AB silicone polyether block copolymers are also known.
  • silicone polyethers are typically made via a platinum catalyzed hydrosilylation reaction in large batch reactors or occasionally in continuous processes. Typically a large molar excess of the unsaturated polyether is needed in such hydrosilylation reactions to account for isomerization of terminal vinyl functionality of the polyoxyalkylene to an unreactive internal position. Since it is impossible to separate the silicone polyether product from un-reacted unsaturated polyether starting materials, product quality and performance is limited in certain applications. Even with an excess of unsaturated hydrocarbon reagent, it is often difficult to achieve the near-complete conversion of silicon- hydride functionality that is typically required as a quality specification.
  • This invention relates to a process for preparing a silicone polyether comprising reacting a mixture comprising:
  • the process of the present is particularly useful to prepare silicone polyethers of improved quality via either a batch or continuous process.
  • Component (A) of the present invention is a polyether having at least one terminally unsaturated aliphatic hydrocarbon group, an alkali metal content of less than 10 ppm and an alkaline earth metal content of less than 0.4 ppm.
  • polyether denotes a polyoxyalkylene copolymer represented by the formula -(C n H2 n O)- wherein n is from 2 to 4 inclusive.
  • the polyoxyalkylene copolymer unit typically may comprise oxyethylene units - (C2H4O)-, oxypropylene units -( ⁇ )-, oxybutylene units -(C4H8O)-, or mixtures thereof.
  • the oxyalkylene units can be arranged in any fashion to form either a block or randomized copolymer structure, but typically form a randomized copolymer group.
  • the polyoxyalkylene comprises both oxyethylene units (C2H4O) and oxypropylene units
  • the polyether (A) may be selected from those having the average formula
  • R 0(C n H2 n O) m R 2 Formula 1 where n is from 2 to 4 inclusive, m is greater than 2, R 1 is a monovalent terminally unsaturated aliphatic hydrocarbon group containing 2 to 12 carbon atoms, R 2 is R 1 , hydrogen, an acetyl group, or a monovalent hydrocarbon group containing 1 to 8 carbons.
  • the polyether is terminated at one end with an unsaturated aliphatic hydrocarbon group containing 2 to 12 carbon atoms, such as an alkenyl or alkynyl group.
  • an unsaturated aliphatic hydrocarbon group containing 2 to 12 carbon atoms such as an alkenyl or alkynyl group.
  • alkynyl groups are shown by the following structures; HC ⁇ C-, HC ⁇ CCH 2 -, HC ⁇ CC(CH 3 )-, HCsCCiCHs) ⁇ , HC ⁇ CC(CH 3 )CH 2 -.
  • Polyethers having an unsaturated aliphatic hydrocarbon group at a molecular terminal are known in the art, and many are commercially available.
  • Representative, non- limiting examples of polyethers, having an alkenyl end group, useful as component (A) include:
  • H 2 C CHCH 2 0(C 2 H 4 0) a H
  • H 2 C CHCH 2 0(C 2 H 4 0) a CH 3
  • H 2 C CHCH 2 0(C 2 H 4 0) a C(0)CH 3
  • H 2 C CHCH 2 0(C 2 H 4 0) a (C 3 H 6 0) b CH 3
  • H 2 C C(CH 3 )CH 2 0(C 2 H 4 0) a H
  • H 2 C CC(CH 3 ) 2 0(C 2 H 4 0) a H
  • H 2 C C(CH 3 )CH 2 0(C 2 H 4 0) a CH 3
  • H 2 C C(CH 3 )CH 2 0(C 2 H 4 0) a C(0)CH 3
  • H 2 C C(CH 3 )CH 2 0(C 2 H 4 0) a (C 3 H 6 0) b CH 3
  • the polyether may also be selected from those as described in US 6,987,157, which is herein incorporated by reference for its teaching of polyethers.
  • the polyether (A) must have an alkali metal content of less than 10 ppm, alternatively, less than 5 ppm, or alternatively less than 2 ppm.
  • ppm denotes parts per million on a weight basis as determined by ICP-MS method.
  • the polyether (A) must have an alkaline earth metal content of less than 0.4 ppm, alternatively, less than 100 ppb.
  • ppb denotes parts per billion on a weight basis as determined by ICP-MS method.
  • Polyethers such as those useful as component (A) are typically prepared by the base catalyzed polymerization of alkylene oxides, such as ethylene, propylene, or butylene oxide.
  • the base catalyst is an alkali metal hydroxide such as sodium or potassium hydroxide.
  • the alkali metal often remains in the resulting polyether product.
  • techniques are known in the art for removing residual alkali metals for such products.
  • non-alkali metal based catalysts are also known in the art.
  • polyether (A) may be any polyether having an alkali metal concentration of less than 10 ppm (parts per million) by weight.
  • Such levels of alkali metal may be achieved by removing alkali metals from polyethers having alkali metal concentrations in excess of 10 ppm by any method known in the art.
  • the polyether (A) may be prepared by a process that does not add, or minimizes, the amount of alkali metals such that the resulting concentration of alkali metal is less than 50 ppm.
  • the alkali metal content may be determined by any analytical method or technique known in the art, such as ICP-MS.
  • Polyether (A) may be any polyether having an alkaline earth metal concentration of less than 10 ppm (parts per million) by weight.
  • the polyether (A) may be prepared by a process that does not add, or minimizes, the amount of alkaline earth metals such that the resulting concentration of alkaline earth metal is less than 10 ppm.
  • the alkali metal content may be determined by any analytical method or technique known in the art, such as ICP-MS.
  • Component (B) of the present invention is an organohydrogensiloxane.
  • an organohydrogensiloxane is any organopolysiloxane containing at least one silicon-bonded hydrogen atom (SiH) per molecule.
  • Organohydrogensiloxanes are well known in the art and are often designated as comprising any number of combination of (R3S1O-1/2), (R2S1O), (RS1O32), (S1O2) siloxy units, where R is independently an organic group or hydrocarbon group.
  • R is methyl in (R3S1O1/2), (R2SKD), (RS1O3/2), siloxy units of an organopolysiloxane
  • the siloxy units are often designated as M, D, and T units respectively while the (S1O2) siloxy unit is designated as a Q unit.
  • Organohydrogensiloxanes have similar structures, but have at least one SiH present on a siloxane unit.
  • methyl based siloxy units in an organohydrogensiloxane can be represented as comprising
  • M H siloxy units (Me2HSiOi/2)' ° H silox y units (MeHSiO), T H siloxy units (HS1O3/2).
  • the organohydrogensiloxanes useful in the present invention may comprise any number of M,
  • organohydrogensiloxane may be selected from organopolysiloxane comprising siloxy units of the average formula:
  • R is an organic group, alternatively R is a hydrocarbon group having 1 to 30 carbons, alternatively R is an alkyl group having 1 to 30 carbons, alternatively R is methyl, and w ⁇ 0, x ⁇ 0, y ⁇ 1 , and z is ⁇ 0.
  • the organohydrogensiloxane is selected from a dimethyl, methyl-hydrogen polysiloxane having the formula:
  • Organohydrogensiloxanes are typically prepared by an acid catalyzed equilibration of a SiH containing siloxane with other siloxanes, such as cyclosiloxanes like octamethylcyclotetrasiloxane.
  • the acid catalyst used in the equilibration reaction is "neutralized" upon completion of the equilibration reaction.
  • the organohydrogensiloxanes suitable in the present invention have an acid number of less than 0.005.
  • the "acid number” is defined as the mass (in mg) of KOH needed to neutralized the acidic species per gram of the organohydrogensiloxane, as determined by titration techniques.
  • the acid number of the organohydrogensiloxane may be determined by titrating the organohydrogensiloxane in an aqueous pyridine solution with a standardized NaOH solution of known normality.
  • the end point may be determined by addition of an indicator, or alternatively, by potentiometric techniques.
  • the acid number is determined by the following calculation:
  • Such titration methods are well known in the art.
  • One representative, non-limiting example is Dow Corning Corporation's Corporate Test Method - CTM 075 (Dow Corning Corp., Midland, Ml 48686).
  • an organohydrogensiloxane suitable as component (B) is prepared in such a manner so the acid number is less than 0.005, or alternatively post treated after production, so as to ensure the acid number is reduced to less than 0.005.
  • Such post treatments typically are effected by contacting the organohydrogensiloxane with a base, such as solid sodium bicarbonate, calcium carbonate, aqueous solutions of such bases, or a basic gas such as ammonia.
  • the organohydrogensiloxane can be further contacted with other solid materials, such as ion exchange resins in a packed bed reactor, or solid carbon, to further reduce the acid number to even lower values.
  • the organohydrogensiloxane is contacted with carbon, as described in US 60/683,754, which is herein incorporated by reference.
  • the organohydrogensiloxane useful as component (B) in the present invention has an acid number of less than 0.005, alternatively less than 0.003, or alternatively less than 0.0015.
  • the organohydrogensiloxane has an acid number less than 0.0015 and the hydrosilylation reaction is done in a batch process.
  • hydrosilylations are known in the art and require the addition of an appropriate hydrosilylation catalyst (C).
  • Suitable hydrosilylation catalysts for use as component (C) in the present invention are known in the art and many are commercially available.
  • the hydrosilylation catalyst is a platinum group metal and is added in an amount of 0.1 to 1000 ppm based on the weight of the reactants (A) and (B), alternatively 1 to 100 ppm of the platinum group metal.
  • the hydrosilylation catalyst may comprise a platinum group metal selected from platinum, rhodium, ruthenium, palladium, osmium, or iridium metal or organometallic compound thereof, or a combination thereof.
  • the hydrosilylation catalyst is exemplified by compounds such as chloroplatinic acid, chloroplatinic acid hexahydrate, platinum dichloride, and complexes of said compounds with low molecular weight organopolysiloxanes or platinum compounds microencapsulated in a matrix or coreshell type structure.
  • Complexes of platinum with low molecular weight organopolysiloxanes include 1 ,3-diethenyl-1 ,1 ,3,3- tetramethykdisiloxane complexes with platinum. These complexes may be microencapsulated in a resin matrix.
  • Suitable hydrosilylation catalysts are described in, for example, U.S. Patents 3,159,601 ; 3,220,972; 3,296,291 ; 3,419,593; 3,516,946; 3,814730; 3,989,668; 4,784,879; 5,036,117; and 5,175,325 and EP 0347895 B1.
  • the hydrosilylation reaction can be conducted neat or in the presence of a solvent.
  • the solvent can be an alcohol such as methanol, ethanol, isopropanol, butanol, or n- propanol; a ketone such as acetone, methylethyl ketone, or methyl isobutyl ketone; an aromatic hydrocarbon such as benzene, toluene, or xylene; an aliphatic hydrocarbon such as heptane, hexane, or octane; a glycol ether such as propylene glycol methyl ether, dipropylene glycol methyl ether, propylene glycol n-butyl ether, propylene glycol n-propyl ether, or ethylene glycol n-butyl ether; a halogenated hydrocarbon such as dichloromethane, 1,1 ,1-trichloroethane or methylene chloride, chloroform,
  • the amount of solvent can be up to 50 weight percent, but is typically from 5 to 25 weight percent, said weight percent being based on the total weight of components in the hydrosilylation reaction.
  • the solvent used during the hydrosilylation reaction can be subsequently removed from the resulting reaction product mixture by various known methods. Typically, this involves heating the contents of the reaction mixture under reduced pressure and collection the volatile solvent.
  • the amount of components (A) and (B) used in the hydrosilylation reaction can vary, and typically the amounts used are expressed as the molar ratio of the total unsaturated groups in component (A) vs the SiH content of component (B).
  • the hydrosilylation reaction is conducted with a slight molar excess of the total unsaturated groups vs SiH to ensure complete consumption of the SiH in the hydrosilylation reaction.
  • the hydrosilylation reaction is conducted with a 20%, alternatively 10%, alternatively 5%, or alternatively 1 % molar excess of the unsaturated group content of the polyether vs the molar SiH content of the organohydrogensiloxane.
  • the hydrosilylation reaction is conducted such that greater than 99.5 mole % of the SiH of the organohydrogensiloxane reacts in the hydrosilylation reaction.
  • the remaining SiH content may be determined by any analytical technique used in the art to measure SiH contents, such as Fourier Transform Infrared (FTIR) spectroscopy, and Si29 NMR techniques.
  • FTIR Fourier Transform Infrared
  • Si29 NMR Si29 NMR techniques.
  • the hydrosilylation reaction is conducted such that greater than 99.9 mole % of the SiH of the organohydrogensiloxane reacts in the hydrosilylation reaction.
  • the hydrosilylation reaction is conducted such that no SiH content is detected by Si29 NMR techniques.
  • the hydrosilylation may be conducted in any batch, semi-continuous, or continuous process known in the art.
  • inventive process disclosed herein can be used to prepare different types of silicone polyether structures, including "rake”, ABA, and (AB) n configurations.
  • Siloxane - refers to an organohydrogensiloxane of average structure M-D8.7DH3.7- M produced by acid catalyzed equilibration of M, D, and DH siloxane intermediates.
  • the "acid number" of the organohydrogensiloxane was determined by Corporate Test Method #0756 (Dow Corning Corporation, Midland Mich.). All of the following examples use a siloxane with acid number of ⁇ 0.001 mg KOH/g acid equivalent.
  • Process 1 Loaded 710.0 grams of Allylpolyether and 290.0 grams Siloxane into a 2 L reaction calorimeter (Mettler-Toledo RC-1). No additional alkali or alkaline earth metals were added during the hydrosilylation Process 1 beyond those from the Allylpolyether. Heated reactor contents to 80 °C in isothermal mode, under a nitrogen atmosphere and with an agitation rate of 600 rpm. Added 0.20 ml of a solution which contains a platinum hydrosilylation catalyst diluted to 2 wt % Pt in isopropanol (3.1 ⁇ g Pt per g reactants). Upon addition of catalyst, an exothermic reaction was initiated.
  • the calorimeter is capable of controlling temperature within +/-1 °C of isothermal while continuously measuring the thermal energy being released by the exothermic chemical reaction.
  • the rate of heat evolution is proportional to rate of the reaction and is plotted either as Kilojoules vs time or as percent Conversion vs time.
  • the reactor contents were maintained at temperature for an additional 10 minutes, then cooled to less than 50° Celsius before being exposed to air.
  • the total conversion achieved in the reaction can be expressed as the total enthalpy evolved during the reaction time.
  • the Total Enthalpy specification for complete reaction is at least 135 kiloJoules.
  • a sample may be taken to test for residual silicon hydride content using Corporate Test Method #0806-1014A (Dow Corning Corporation, Midland Mich.)
  • a silicone polyether was prepared using Process 1 with an Allylpolyether containing 0.924 parts per million residual Na, 0.433 parts per million residual K, and no detectable residual Mg or Ca and siloxane with ⁇ 0.001 mg KOH/g acid equivalent (acid number).
  • the reaction had a total enthalpy of 135.0 kiloJoules. A value of at least 135 kiloJoules is acceptable because it corresponds to a sufficiently complete reaction.
  • a silicone polyether was prepared using Process 1 with an Allylpolyether containing 0.558 parts per million residual Na, 0.446 parts per million residual K, and no detectable residual Mg or Ca and siloxane with ⁇ 0.001 mg KOH/g acid equivalent (acid number). The reaction had a total enthalpy of 136.1 kiloJoules.
  • a silicone polyether was prepared using Process 1 with an Allylpolyether containing 0.743 parts per million residual Na, 1.769 parts per million residual K, 1.047 parts per million residual Mg, and 0.125 parts per million residual Ca, and siloxane with ⁇ 0.001 mg KOH/g acid equivalent (acid number).
  • the reaction had a total enthalpy of 131.6 kiloJoules.
  • a silicone polyether was prepared using Process 1 with an Allylpolyether containing 2.661 parts per million residual Na, 0.593 parts per million residual K, 0.326 parts per million residual Mg, and 0.102 parts per million residual Ca, and siloxane with ⁇ 0.001 mg KOH/g acid equivalent (acid number).
  • the reaction had a total enthalpy of 123.7 kiloJoules.
  • a silicone polyether was prepared using Process 1 with an Allylpolyether containing 10.34 parts per million residual Na, 0.113 parts per million residual K, 0.759 parts per million residual Mg, and no detectable residual Ca.
  • the reaction had a total enthalpy of 112.8 kiloJoules.
  • a silicone polyether was prepared using Process 1 with an Allylpolyether containing 37.2 parts per million residual Na, 0.102 parts per million residual K, and no detectable Mg or Ca, and siloxane with ⁇ 0.001 mg KOH/g acid equivalent (acid number). The reaction had a total enthalpy of 131.7 kiloJoules.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Silicon Polymers (AREA)

Abstract

L'invention concerne un procédé de préparation de polyéther de silicone en faisant réagir un mélange comprenant (A) un polyéther ayant au moins un groupe hydrocarboné à insaturation terminale et une teneur en métal alcalin inférieure à 10 ppm, et une teneur en métal alcalino-terreux inférieure à 0,4 ppm, (B) un organohydrogénosiloxane ayant un indice d'acide inférieur à 0,005, et (C) un catalyseur de réaction d'hydrosilylation.
PCT/US2018/013958 2017-02-09 2018-01-17 Procédé de préparation de polyéthers de silicone Ceased WO2018147979A1 (fr)

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US62/456,685 2017-02-09

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111825843A (zh) * 2019-04-16 2020-10-27 中国科学院大连化学物理研究所 一种离子型铱配合物催化脱氢偶联合成部分可再生聚硅醚的方法
US20220363837A1 (en) * 2019-12-16 2022-11-17 Dow Silicones Corporation Low isomer hydrosilylation
CN116199886A (zh) * 2022-12-19 2023-06-02 浙江润禾有机硅新材料有限公司 一种耐酸碱有机硅表面活性剂及其制备方法

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US3159601A (en) 1962-07-02 1964-12-01 Gen Electric Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes
US3220972A (en) 1962-07-02 1965-11-30 Gen Electric Organosilicon process using a chloroplatinic acid reaction product as the catalyst
US3296291A (en) 1962-07-02 1967-01-03 Gen Electric Reaction of silanes with unsaturated olefinic compounds
US3419593A (en) 1965-05-17 1968-12-31 Dow Corning Catalysts for the reaction of = sih with organic compounds containing aliphatic unsaturation
US3516946A (en) 1967-09-29 1970-06-23 Gen Electric Platinum catalyst composition for hydrosilation reactions
US3814730A (en) 1970-08-06 1974-06-04 Gen Electric Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes
US3989668A (en) 1975-07-14 1976-11-02 Dow Corning Corporation Method of making a silicone elastomer and the elastomer prepared thereby
US4784879A (en) 1987-07-20 1988-11-15 Dow Corning Corporation Method for preparing a microencapsulated compound of a platinum group metal
US5036117A (en) 1989-11-03 1991-07-30 Dow Corning Corporation Heat-curable silicone compositions having improved bath life
US5175325A (en) 1991-02-14 1992-12-29 Dow Corning Limited Platinum complexes and use thereof
EP0347895B1 (fr) 1988-06-23 1993-11-18 Toray Silicone Company, Limited Procédé de préparation des compositions en forme de particules comprenant un catalyseur d'hydrosilation à base de platine et une résine de silicone
US6987157B2 (en) 2001-01-08 2006-01-17 Dow Corning Corporation Certain silicone polyethers, methods for making them and uses
WO2007127004A1 (fr) * 2006-03-31 2007-11-08 Dow Corning Corporation Procédés de préparation des polyéthers de silicone

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3159601A (en) 1962-07-02 1964-12-01 Gen Electric Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes
US3220972A (en) 1962-07-02 1965-11-30 Gen Electric Organosilicon process using a chloroplatinic acid reaction product as the catalyst
US3296291A (en) 1962-07-02 1967-01-03 Gen Electric Reaction of silanes with unsaturated olefinic compounds
US3419593A (en) 1965-05-17 1968-12-31 Dow Corning Catalysts for the reaction of = sih with organic compounds containing aliphatic unsaturation
US3516946A (en) 1967-09-29 1970-06-23 Gen Electric Platinum catalyst composition for hydrosilation reactions
US3814730A (en) 1970-08-06 1974-06-04 Gen Electric Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes
US3989668A (en) 1975-07-14 1976-11-02 Dow Corning Corporation Method of making a silicone elastomer and the elastomer prepared thereby
US4784879A (en) 1987-07-20 1988-11-15 Dow Corning Corporation Method for preparing a microencapsulated compound of a platinum group metal
EP0347895B1 (fr) 1988-06-23 1993-11-18 Toray Silicone Company, Limited Procédé de préparation des compositions en forme de particules comprenant un catalyseur d'hydrosilation à base de platine et une résine de silicone
US5036117A (en) 1989-11-03 1991-07-30 Dow Corning Corporation Heat-curable silicone compositions having improved bath life
US5175325A (en) 1991-02-14 1992-12-29 Dow Corning Limited Platinum complexes and use thereof
US6987157B2 (en) 2001-01-08 2006-01-17 Dow Corning Corporation Certain silicone polyethers, methods for making them and uses
WO2007127004A1 (fr) * 2006-03-31 2007-11-08 Dow Corning Corporation Procédés de préparation des polyéthers de silicone
US8008407B2 (en) 2006-03-31 2011-08-30 Dow Corning Corporation Process for preparing silicone polyethers

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111825843A (zh) * 2019-04-16 2020-10-27 中国科学院大连化学物理研究所 一种离子型铱配合物催化脱氢偶联合成部分可再生聚硅醚的方法
CN111825843B (zh) * 2019-04-16 2021-08-31 中国科学院大连化学物理研究所 一种离子型铱配合物催化脱氢偶联合成部分可再生聚硅醚的方法
US20220363837A1 (en) * 2019-12-16 2022-11-17 Dow Silicones Corporation Low isomer hydrosilylation
CN116199886A (zh) * 2022-12-19 2023-06-02 浙江润禾有机硅新材料有限公司 一种耐酸碱有机硅表面活性剂及其制备方法

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