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WO2005118682A1 - Réaction de condensation des silicones - Google Patents

Réaction de condensation des silicones Download PDF

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Publication number
WO2005118682A1
WO2005118682A1 PCT/US2004/015848 US2004015848W WO2005118682A1 WO 2005118682 A1 WO2005118682 A1 WO 2005118682A1 US 2004015848 W US2004015848 W US 2004015848W WO 2005118682 A1 WO2005118682 A1 WO 2005118682A1
Authority
WO
WIPO (PCT)
Prior art keywords
silicon
compound
group
silicon atom
siloxane
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2004/015848
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English (en)
Inventor
Slawomir Rubinsztajn
James Anthony Cella
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
General Electric Co
Original Assignee
General Electric Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by General Electric Co filed Critical General Electric Co
Priority to CNA2004800436104A priority Critical patent/CN1989178A/zh
Priority to PCT/US2004/015848 priority patent/WO2005118682A1/fr
Priority to EP04776060A priority patent/EP1756200A1/fr
Priority to JP2007527158A priority patent/JP2007538070A/ja
Priority to BRPI0418817-9A priority patent/BRPI0418817A/pt
Publication of WO2005118682A1 publication Critical patent/WO2005118682A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C08G77/06—Preparatory processes
    • C08G77/08—Preparatory processes characterised by the catalysts used

Definitions

  • the present invention relates to a new condensation reaction between compounds containing the hydrogen bonded directly to silicon (organo- hydrosilanes or organo-hydrosiloxanes) and alkoxy-silane or siloxane which leads to the formation of siloxane bond and release of hydrocarbons as a byproduct.
  • Two general processes can be applied for synthesis of organosiloxane polymers; ring opening polymerization of cyclic siloxanes and polycondensation.
  • the polycondensation reaction between organofunctional silanes or oligosiloxanes leads to the formation of siloxane bond and elimination of a low molecular byproduct.
  • the polycondensation of low molecular weight siloxanol oils is the most common method synthesis of polyorganosiloxanes and has been practiced for several years.
  • the byproduct of this process is water. Unfortunately this method cannot be used for the synthesis of well-defined block organosiloxane copolymers. In that case the non-hydrolyric condensation processes can be employed. Many of such reactions are known and are frequently used:
  • organosilanol moiety will react with a hydrogen atom bonded directly to silicon (organo- hydrosilane) to produce a hydrogen molecule and the silicon-oxygen bond, (See, "Silicon in Organic, Organometallic and Polymer Chemistry” Michael A. Brook, John Wiley & Sons, Inc., New York, Chichester, Weinheim, Brisbane, Singapore, Toronto, 2000).
  • a transition metal catalyst especially noble metal catalysts such as those comprising platinum, palladium, etc., a basic catalyst such as an alkali metal hydroxide, amine, etc., or a Lewis acid catalyst such as a tin compound, etc.
  • a transition metal catalyst especially noble metal catalysts such as those comprising platinum, palladium, etc., a basic catalyst such as an alkali metal hydroxide, amine, etc., or a Lewis acid catalyst such as a tin compound, etc.
  • organo-boron compounds are extremely efficient catalysts for the reaction between an organo-hydrosilanes and organosilanols (WO 01/74938 Al). Unfortunately, the by-product of this process is dangerous, highly reactive hydrogen.
  • the present invention provides for a new condensation process to forming a silicon-oxygen bond comprising reacting an organosilane or siloxane compounds bearing at least one hydrosilane functional group with an organoalkoxysilane or siloxane compounds containing at least one alkoxysilane functional group and release of hydrocarbon as a byproduct, in the presence of a Lewis acid catalyst.
  • the present invention also provides for the formation of silicon-oxygen bond by reacting a compound comprising both at least one hydrosilane functionality and at least one an alkoxysilane moiety and releases hydrocarbon as a byproduct in the presence of a Lewis acid catalyst.
  • the present invention provides for a process for forming a silicon to oxygen bond comprising: (a) reacting a first silicon containing compound said first silicon containing compound comprising a hydrogen atom directly bonded to a silicon atom with (b) a second silicon containing compound said second silicon containing compound comprising an alkoxy group bonded to a silicon atom, in the presence of (c) a Lewis acid catalyst thereby forming a silicon to oxygen bond.
  • the present invention also provides for a process for forming an silicon to oxygen bond comprising: (a) selecting a compound comprising both at least one hydrogen atom directly bonded to a silicon atom and at least one an alkoxy group bonded to a silicon atom in said compound and (b) reacting the hydrosilane functional group with the alkoxysilane group, in the presence of (c) a Lewis acid catalyst thereby forming a silicon to oxygen bond.
  • the processes of the present invention further provide for means to produce compositions: siloxane foams, hyperbranched silicone polymers, cross-linked siloxane networks and gels therefrom as well as other silicone and siloxane molecules exemplified herein.
  • the present invention represents the discovery of a new type of non- hydrolytic condensation reaction for silicon bearing molecules.
  • the reaction may be characterized as a condensation reaction between an organo hydrosilane or siloxane compounds bearing at least one hydrosilane moiety with an organoalkoxysilane or siloxane compounds containing at least one alkoxysilane moiety or functionality in the following exemplary embodiment: the reaction of (M a DbT c Q d ) e (R 2 )f(R 3 ) g SiOCH 2 R 1 and HSi(R 4 )h(R 5 )i(MaD b T c Qd)j yields a compound containing a new silicon-oxygen bond (MaDbT c Qd)e(R 2 )f(R 3 )gSiOSi(R 4 )h(R 5 )i(MaDbTcQd)j and hydrocarbon (CH3R 1 ) as the products.
  • the other molecular components have standard definitions as follows:
  • the R 1 substituent is hydrogen or is independently selected from the group of one to sixty carbon atom monovalent hydrocarbon radicals that may or may not be substituted with halogens (halogen being F, CI, Br and I), e.g. non limiting examples being fluoroalkyl substituted or chloroalkyl substituted, substituents R 2 , R 4 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are independently selected from the group of one to sixty carbon atom monovalent hydrocarbon radicals that may or may not be substituted with halogens (halogen being F, CI, Br and I), e.g.
  • R 3 and R 5 are independently selected from the group consisting of hydrogen, one to sixty carbon atom monovalent alkoxy radicals, one to sixty carbon atom monovalent aryloxy radicals, one to sixty carbon atom monovalent alkaryloxy radicals and halogen.
  • a preferred structure of the polymer with ( ⁇ Si-H) groups has the following formula:
  • the above reaction is generally accomplished in the presence of an appropriate catalyst.
  • the catalyst for this reaction is preferably a Lewis acid catalyst.
  • a "Lewis acid” is any substance that will take up an electron pair to form a covalent bond (i.e., "electron- pair acceptor”).
  • This concept of acidity also includes the "proton donor” concept of the Lowry- Bronsted definition of acids.
  • boron trifluoride (BF3) is a typical Lewis acid, as it contains only six electrons in its outermost electron orbital shell. BF3 tends to accept a free electron pair to complete its eight- electron orbital.
  • Preferred Lewis acid catalysts include such catalysts as FeCfe, AICI3, ZnQb, ZnBr2, BF3.
  • Lewis acid catalysts having a greater solubility in siloxane media are more preferred and preferable catalysts include Lewis acid catalysts of formula (I)
  • each R 12 is independently the same (identical) or different and represent a monovalent aromatic hydrocarbon radical having from 6 to 14 carbon atoms, such monovalent aromatic hydrocarbon radicals preferably having at least one electron-withdrawing element or group such as -CF3, -NO2 or -CN, or substituted with at least two halogen atoms;
  • X is a halogen atom;
  • x is 1, 2, or 3; and
  • each R 13 are independently the same (identical) or different and represent a monovalent aromatic hydrocarbon radical having from 6 to 14 carbon atoms, such monovalent aromatic hydrocarbon radicals preferably having at least one electron-withdrawing element or group such as -CF3, - NO2 or -CN, or substituted with at least two halogen atoms;
  • X is a halogen atom;
  • x is 1, 2, or 3; and
  • condensation reaction appears to require an alkoxy silane of the following structure ( ⁇ Si-O- CH2-R 1 ) wherein R 1 is Ci- ⁇ o alkyl, G-60 alkoxy, C2-60 alkenyl, C ⁇ - ⁇ o aryl, and C6-60 alkyl-substituted aryl, and C6-60 arylalkyl where the alkyl groups may be halogenated, for example, fluorinated to contain fluorocarbons such as C1-22 fluoroalkyl.
  • the preferred alkoxy group is methoxy and ethoxy group.
  • the process of the present invention utilizes a Lewis acid catalyst concentration that ranges from about 1 part per million by weight to about 10 weight percent (based on the total weight of siloxanes being reacted); preferably from about 10 part per million by weight (wppm) to about 5 weight percent (50,000 wppm), more preferably from about 50 wppm to about 10,000 wppm and most preferably from about 50 wppm to about 5,000 wppm.
  • the condensation reaction can be done without solvent or in the presence of solvents.
  • the presence of solvents may be beneficial due to an increased ability to control viscosity, rate of the reaction and exothermicity of the process.
  • the preferred solvents include aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, as well as oligomeric cyclic diorganosiloxanes.
  • the condensation reaction between the ( ⁇ Si-H) moiety and the ( ⁇ SiOCHzR 1 ) moiety can be conducted at an ambient or at an elevated temperature depending on the chemical structures of reagents and catalysts, concentration of catalyst and used solvent.
  • siloxane oligomers or polymers that bear at least one ( ⁇ SiOQHfcR 1 ) moiety with the siloxane oligomers or polymers having at least one (H-Si ⁇ ) functional group and Lewis acid catalyst. Subsequently the condensation reaction may be activated by heat. To extend the pot life of such a fully formulated mixture, the addition of a stabilizing agent is recommended.
  • the stabilizing additives that are effective belong to the group of nucleophiles that are able to form a complex with Lewis acids.
  • These stabilizing additives, preferably nucleophilic compounds include but are not limited to ammonia, primary amines, secondary amines, tertiary amines, organophosphines and phosphines.
  • compositions produced according to the method or process of this invention are useful in the field of siloxane elastomers, siloxane coatings, insulating materials and cosmetic products.
  • the condensation reaction of ( ⁇ Si- H) terminated dimethylsiloxane oligomers with alkoxy-terminated diphenylsiloxane oligomers leads to a formation of regular block siloxane copolymers with beneficial thermo-mechanical properties.
  • the crosslinked material produced via condensation of siloxane oligomers and polymers that bear more than one ( ⁇ SiOCHzR 1 ) moiety with the siloxane oligomers and polymers having more than one (H-Si ⁇ ) functional group will lead to a formation of novel siloxane coatings and siloxane foams.
  • a low cross-link density network frequently has the ability to be swollen by lower molecular weight siloxanes or hydrocarbons thereby forming a gel.
  • Such gels have found utility as silicone structurants for cosmetic compositions.
  • Hyperbranched siloxane polymers may be prepared by reacting the self- condensation of molecule that bears more than one ( ⁇ SiOCH ⁇ R 1 ) and one (H- Si ⁇ ) functionalities in the presence of Lewis acid.
  • silicon is a tetravalent element and for purposes of descriptive convenience herein, not all four bonds of the silicon atom have been described in some of the abbreviated chemical reaction scenarios used to explain the reaction chemistry involved in the formation of non-hydrolytic silicon oxygen bonds. Where silicon is hypovalent or hypervalent in terms of its customary stereochemistry, the full structure has been indicated.
  • Si 29 NMR indicated the formation of linear alkoxy-stopped siloxane oligomers along with small amounts of D3 (hexamethylcyclotrisiloxane) and D4 (octamethyl cyclotetrasiloxane). This low temperature process may also be carried out a room temperature.
  • Example 8 shows that sterically hindered alkoxysilanes such as isopropoxysilane or t-butyloxysilane do not react with Si-H in the presence of B(C 6 F5)3.
  • the condensation reaction requires the presence of -O-CH2-R 1 alkoxide moiety attached to silicon atom.
  • the word "comprises” and its grammatical variants logically also subtend and include phrases of varying and differing extent such as for example, but not limited thereto, “consisting essentially of” and “consisting of.” Where necessary, ranges have been supplied, those ranges are inclusive of all sub-ranges there between. It is to be expected that variations in these ranges will suggest themselves to a practitioner having ordinary skill in the art and where not already dedicated to the public, those variations should where possible be construed to be covered by the appended claims.

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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

Une nouvelle réaction de condensation des silicones, la condensation entre un alcoxy silane ou siloxane et un organo-hydrosilane ou -siloxane et des catalyseurs, est par conséquent décrite et revendiquée.
PCT/US2004/015848 2004-05-20 2004-05-20 Réaction de condensation des silicones Ceased WO2005118682A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CNA2004800436104A CN1989178A (zh) 2004-05-20 2004-05-20 硅氧烷缩合反应
PCT/US2004/015848 WO2005118682A1 (fr) 2004-05-20 2004-05-20 Réaction de condensation des silicones
EP04776060A EP1756200A1 (fr) 2004-05-20 2004-05-20 Réaction de condensation des silicones
JP2007527158A JP2007538070A (ja) 2004-05-20 2004-05-20 シリコーン縮合反応
BRPI0418817-9A BRPI0418817A (pt) 2004-05-20 2004-05-20 reação de condensação do silicone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2004/015848 WO2005118682A1 (fr) 2004-05-20 2004-05-20 Réaction de condensation des silicones

Publications (1)

Publication Number Publication Date
WO2005118682A1 true WO2005118682A1 (fr) 2005-12-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2004/015848 Ceased WO2005118682A1 (fr) 2004-05-20 2004-05-20 Réaction de condensation des silicones

Country Status (5)

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EP (1) EP1756200A1 (fr)
JP (1) JP2007538070A (fr)
CN (1) CN1989178A (fr)
BR (1) BRPI0418817A (fr)
WO (1) WO2005118682A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009138097A (ja) * 2007-12-06 2009-06-25 Toyota Central R&D Labs Inc シリカ系材料およびその製造方法
US7863361B2 (en) 2005-11-15 2011-01-04 Momentive Performance Materials Inc. Swollen silicone composition, process of producing same and products thereof
US8017687B2 (en) 2005-11-15 2011-09-13 Momentive Performance Materials Inc. Swollen silicone composition and process of producing same
US8048819B2 (en) 2005-06-23 2011-11-01 Momentive Performance Materials Inc. Cure catalyst, composition, electronic device and associated method
WO2021262776A1 (fr) 2020-06-24 2021-12-30 Dow Global Technologies Llc Durcissement et fonctionnalisation d'interpolymères d'oléfine/silane
US20220033589A1 (en) * 2018-12-21 2022-02-03 Dow Silicones Corporation Polyfunctional organosiloxanes, compositions containing same, and methods for the preparation thereof
JP2023532198A (ja) * 2020-06-24 2023-07-27 ダウ シリコーンズ コーポレーション フッ素化アリールボランルイス酸によって触媒される有機ケイ素化合物とシリルヒドリドとの反応のための組成物及び方法
JP2023535667A (ja) * 2020-06-24 2023-08-21 ダウ シリコーンズ コーポレーション フッ素化アリールボランルイス酸によって触媒されるシリルヒドリド反応のための組成物及び方法

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US8372504B2 (en) * 2009-01-13 2013-02-12 Korea Advanced Institute Of Science And Technology Transparent composite compound
CN101899156B (zh) * 2010-05-04 2012-06-27 中山大学 一种多链梯形聚烷基硅倍半氧烷的制备方法
US8865926B2 (en) * 2011-09-26 2014-10-21 Sivance, Llc Process for the production of cyclosiloxanes
CN103897190B (zh) * 2012-12-25 2017-07-18 深圳市嘉达高科产业发展有限公司 一种有机硅树脂及其制备方法
US9530946B2 (en) * 2013-04-12 2016-12-27 Milliken & Company Light emitting diode
US9422317B2 (en) * 2013-04-12 2016-08-23 Milliken & Company Siloxane compound and process for producing the same
CN108440592B (zh) * 2018-03-23 2020-06-05 威海新元化工有限公司 一种1,5-二乙烯基-1,1,3,3,5,5-六甲基三硅氧烷的制备方法
EP3898774B1 (fr) * 2018-12-21 2023-06-07 Dow Silicones Corporation Méthode de préparation d'un organopolysiloxane fonctionalisé
JP7560490B2 (ja) 2019-06-04 2024-10-02 ダウ シリコーンズ コーポレーション Ｓｉ－Ｈとエポキシドとの反応のための熱誘発としての架橋型フラストレイテッドルイスペア
KR20220016904A (ko) 2019-06-04 2022-02-10 다우 실리콘즈 코포레이션 실릴 수소화물과 알파-베타 불포화 에스테르 사이의 열적으로 개시되는 산 촉매 반응
CN113993933B (zh) * 2019-06-04 2023-07-14 美国陶氏有机硅公司 作为用于Si-H和Si-OR之间的反应的热触发剂的桥联受阻路易斯对
US12116459B2 (en) 2019-06-04 2024-10-15 Dow Silicones Corporation Thermally initiated acid catalyzed reaction between silyl hydride and silyl ether and/or silanol
WO2020247329A1 (fr) 2019-06-04 2020-12-10 Dow Silicones Corporation Réaction catalysée par un acide initiée thermiquement entre un hydrure de silyle et un siloxane
EP3980426B1 (fr) 2019-06-04 2023-04-19 Dow Silicones Corporation Paires de lewis frustrées pontées en tant que déclencheur thermique pour des réactions entre si-h et si-o-si
JP7560489B2 (ja) 2019-06-04 2024-10-02 ダウ シリコーンズ コーポレーション Ｓｉ－Ｈとアルファ－ベータ不飽和エステルとの反応のための熱トリガとしての架橋型フラストレイテッドルイスペア
US12173181B2 (en) 2020-06-04 2024-12-24 Dow Silicones Corporation Epoxy-curable silicone release coating composition and methods for its preparation and use

Citations (3)

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Publication number Priority date Publication date Assignee Title
EP0291871A2 (fr) 1987-05-15 1988-11-23 Wacker-Chemie GmbH Procédé de préparation d'organopolysiloxanes et organopolysiloxane pouvant être obtenue par ce procédé
US20030139287A1 (en) * 2000-04-04 2003-07-24 Thomas Deforth Use of a boron derivative as heat-activated catalyst for polymerisation and/or crosslinking of silicone by dehydrogenative condensation
US20030195370A1 (en) * 2000-04-15 2003-10-16 Taylor Richard Gregory Process for the condensation of compounds having silicon bonded hydroxy or alkoxy groups

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0291871A2 (fr) 1987-05-15 1988-11-23 Wacker-Chemie GmbH Procédé de préparation d'organopolysiloxanes et organopolysiloxane pouvant être obtenue par ce procédé
US20030139287A1 (en) * 2000-04-04 2003-07-24 Thomas Deforth Use of a boron derivative as heat-activated catalyst for polymerisation and/or crosslinking of silicone by dehydrogenative condensation
US20030195370A1 (en) * 2000-04-15 2003-10-16 Taylor Richard Gregory Process for the condensation of compounds having silicon bonded hydroxy or alkoxy groups

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8048819B2 (en) 2005-06-23 2011-11-01 Momentive Performance Materials Inc. Cure catalyst, composition, electronic device and associated method
US7863361B2 (en) 2005-11-15 2011-01-04 Momentive Performance Materials Inc. Swollen silicone composition, process of producing same and products thereof
US8017687B2 (en) 2005-11-15 2011-09-13 Momentive Performance Materials Inc. Swollen silicone composition and process of producing same
JP2009138097A (ja) * 2007-12-06 2009-06-25 Toyota Central R&D Labs Inc シリカ系材料およびその製造方法
US20220033589A1 (en) * 2018-12-21 2022-02-03 Dow Silicones Corporation Polyfunctional organosiloxanes, compositions containing same, and methods for the preparation thereof
US11643506B2 (en) * 2018-12-21 2023-05-09 Dow Silicones Corporation Polyfunctional organosiloxanes, compositions containing same, and methods for the preparation thereof
WO2021262776A1 (fr) 2020-06-24 2021-12-30 Dow Global Technologies Llc Durcissement et fonctionnalisation d'interpolymères d'oléfine/silane
JP2023532198A (ja) * 2020-06-24 2023-07-27 ダウ シリコーンズ コーポレーション フッ素化アリールボランルイス酸によって触媒される有機ケイ素化合物とシリルヒドリドとの反応のための組成物及び方法
JP2023535667A (ja) * 2020-06-24 2023-08-21 ダウ シリコーンズ コーポレーション フッ素化アリールボランルイス酸によって触媒されるシリルヒドリド反応のための組成物及び方法
JP7712962B2 (ja) 2020-06-24 2025-07-24 ダウ シリコーンズ コーポレーション フッ素化アリールボランルイス酸によって触媒されるシリルヒドリド反応のための組成物及び方法
JP7748400B2 (ja) 2020-06-24 2025-10-02 ダウ シリコーンズ コーポレーション フッ素化アリールボランルイス酸によって触媒される有機ケイ素化合物とシリルヒドリドとの反応のための組成物及び方法

Also Published As

Publication number Publication date
BRPI0418817A (pt) 2007-11-13
EP1756200A1 (fr) 2007-02-28
CN1989178A (zh) 2007-06-27
JP2007538070A (ja) 2007-12-27

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