WO1998037126A1 - Verfahren zur herstellung von organofunktionellen siloxanen und deren verwendung - Google Patents
Verfahren zur herstellung von organofunktionellen siloxanen und deren verwendung Download PDFInfo
- Publication number
- WO1998037126A1 WO1998037126A1 PCT/EP1998/000700 EP9800700W WO9837126A1 WO 1998037126 A1 WO1998037126 A1 WO 1998037126A1 EP 9800700 W EP9800700 W EP 9800700W WO 9837126 A1 WO9837126 A1 WO 9837126A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- dialkylsiloxane
- catalyst
- sio
- compound
- Prior art date
Links
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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- 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
- C08G77/10—Equilibration processes
-
- 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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
Definitions
- the present invention relates to a process for the preparation of Si-O-C-linked organofunctional siloxanes and their use
- Organofunctionally modified siloxanes have a wide range of applications for modifying organic polymers.
- the production of the siloxanes has hitherto been carried out using two-stage production processes in which the siloxane framework is first built up and then, in a second step, the desired organofunctional group is introduced
- DE-A 3 334 782 discloses the reaction of an acetoxy-terminated polysiloxane with dihydroxy compounds with elimination of acetic acid, while in US Pat. No. 578,562 the reaction of an SiOH-stopped polysiloxane with diols
- the object of the present invention was to provide a simplified method for producing organofunctional siloxanes
- the invention therefore relates to a process for the preparation of organofunctional polydiorganosiloxanes of the formula (I) [R 2 (XR , O) S ⁇ O I / 2 ] 1 [R 2 S ⁇ O 2/2 ] "[RS I O 1/2 ] 2 l
- the t ⁇ methylsiloxy groups are preferably added as hexamethyldisiloxane.
- This mixture is preferably a mixture obtained in the hydrolysis of chlorosilanes.
- water is formed by condensation the SiOH group
- a hydrophobic solvent is preferably used for easier removal of the water of reaction
- An aquiliberation catalyst is understood to mean a catalyst which is responsible for both the chain structure and the chain degradation in the reaction
- perfluoroalkylsulfonic acids preferably ci- to C ⁇ -perfluoroalkylsulfonic acids, individually or in a mixture with sulfuric acid, or alkali metal hydroxides, preferably potassium and casium hydroxide, are preferably used as aquilation catalysts, preferably the aquatic fermentation catalyst is used in amounts of 500-5000 ppm. based on the amounts of cyclic dialkylsiloxane and the compound HO-R'-X used
- ether particularly affects diols which can form cyclic 5 or 6-membered ethers, such as the formation of dimethyltetrahydrofuran from 2.5 hexanediol.
- the cleavage of diols is observed particularly in the case of bishydroxyphenylalkanes, such as, for example, in the reaction of 2,2-bis (4-hydroxyphenyl) propane to give phenol and isopropenylphenol. These reactions can be partially avoided by a suitable choice of catalyst.
- Basic catalysts such as cesium hydroxide are preferred as catalysts.
- the cyclic dialkylsiloxane is preferably used in a ratio of 1 to 500 mol of dialkylsiloxy groups to 2 mol of the compound of the HO-R'-X type.
- the hydrophobic solvent used in the process according to the invention preferably has a boiling point> 100 ° C. at atmospheric pressure and / or forms an azeotrope with water.
- a boiling point> 100 ° C. at atmospheric pressure and / or forms an azeotrope with water preferably has a boiling point> 100 ° C. at atmospheric pressure and / or forms an azeotrope with water.
- the process involves a certain solubility of the HOR'X type compound used in the solvent used and / or in the siloxane.
- Xylene, toluene or chlorobenzene are preferably used.
- the HOR'X compound used has a boiling point above the solvent used and does not form an azeotrope with water.
- the following are preferred combinations: toluene hydroquinone, xylene hydroquinone, xylene / 2,2-bis (hydroxymethyl-1-butenol) diallyl ether and xylene / 2,2-bis (4-hydroxycyclohexyl) propane.
- Siloxane chain as alcohols, e.g. 2,2-bis (4-hydroxycyclohexyl) propane, in which there is no interaction between the OH groups.
- the more reactive primary OH group preferably reacts with the siloxane.
- the process according to the invention can be ended by neutralizing the catalyst.
- neutralization preference is given to those neutralizing agents which are to be removed completely from the product after the reaction mixture has been worked up.
- NaHCO 3 NaHCO 3 , soda and (NH4) 2 CO 3 are used in basic catalysis
- the invention also relates to the use of the organofunctional siloxanes produced by the process according to the invention for modifying organic polymers.
- the incorporation into the polymer structure is to take place by reaction of the O-Si (R 2 ) -O-R'X groups formed with the organic monomers or oligomers.
Landscapes
- 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
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/367,668 US6258968B1 (en) | 1997-02-20 | 1998-02-09 | Method for producing organofunctional siloxanes and use of same |
EP98909423A EP0963397A1 (de) | 1997-02-20 | 1998-02-09 | Verfahren zur herstellung von organofunktionellen siloxanen und deren verwendung |
AU63964/98A AU6396498A (en) | 1997-02-20 | 1998-02-09 | Method for producing organofunctional siloxanes and use of same |
JP53620798A JP2001512511A (ja) | 1997-02-20 | 1998-02-09 | 有機官能シロキサン類の製造方法およびそれの使用 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19706646 | 1997-02-20 | ||
DE19706646.1 | 1997-02-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998037126A1 true WO1998037126A1 (de) | 1998-08-27 |
Family
ID=7820891
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/000700 WO1998037126A1 (de) | 1997-02-20 | 1998-02-09 | Verfahren zur herstellung von organofunktionellen siloxanen und deren verwendung |
Country Status (5)
Country | Link |
---|---|
US (1) | US6258968B1 (de) |
EP (1) | EP0963397A1 (de) |
JP (1) | JP2001512511A (de) |
AU (1) | AU6396498A (de) |
WO (1) | WO1998037126A1 (de) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002060972A2 (en) * | 2001-01-29 | 2002-08-08 | Ndsu Research Foundation | Antineoplastic polyalkoxyalkylsiloxanes and methods of use thereof |
US6482912B2 (en) * | 2001-01-29 | 2002-11-19 | Ndsu Research Foundation | Method of preparing aminofunctional alkoxy polysiloxanes |
CN101657505B (zh) * | 2007-01-10 | 2012-09-26 | 沙伯基础创新塑料知识产权有限公司 | 低烟气密度聚(亚芳基醚)组合物,方法,和制品 |
KR101904570B1 (ko) | 2011-05-17 | 2018-10-04 | 모멘티브 퍼포먼스 머티리얼즈 게엠베하 | 폴리실록산-폴리오가노 블록 공중합체 |
CA2869906A1 (en) | 2012-04-10 | 2013-10-17 | Momentive Performance Materials Gmbh | Process for producing functional siloxanes of controlled structure |
EP3036272B1 (de) | 2013-08-23 | 2017-12-13 | Momentive Performance Materials Inc. | Katalysator zur synthese von siloxanen |
CN105637012B (zh) * | 2013-10-08 | 2019-03-08 | 科思创德国股份有限公司 | 聚硅氧烷-聚碳酸酯嵌段共缩合物 |
WO2015052112A1 (en) * | 2013-10-08 | 2015-04-16 | Bayer Materialscience Ag | Process for preparing polysiloxane-polycarbonate block cocondensates |
KR102294921B1 (ko) * | 2013-10-08 | 2021-08-30 | 코베스트로 도이칠란트 아게 | 약산의 염을 이용하는 폴리실록산-폴리카보네이트 블록 공축합물의 제조 방법 |
WO2015052110A1 (en) * | 2013-10-08 | 2015-04-16 | Bayer Materialscience Ag | Preparation of siloxane-containing block copolycarbonates by means of reactive extrusion |
CN106687506A (zh) | 2014-07-03 | 2017-05-17 | 莫门蒂夫性能材料股份有限公司 | 酯官能的聚硅氧烷和由其制成的共聚物 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2714807A1 (de) * | 1976-04-08 | 1977-10-20 | Goldschmidt Ag Th | Verfahren zur herstellung aequilibrierter organopolysiloxangemische mit am silicium gebundenen organosulfonsaeuregruppen |
DE3112735A1 (de) * | 1980-04-04 | 1982-04-01 | General Electric Co., Schenectady, N.Y. | "als hydraulische fluessigkeit brauchbare silicon-fluessigkeit und verfahren zur kraftuebertragung" |
DE3334782A1 (de) * | 1983-04-19 | 1984-10-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polydiorganosiloxanen mit hydroxyaryloxy-endgruppen |
EP0317840A1 (de) * | 1987-11-25 | 1989-05-31 | General Electric Company | Katalysator zur Herstellung von Polyfluorosiloxanen |
EP0365938A2 (de) * | 1988-10-24 | 1990-05-02 | General Electric Company | Saure Equilibrierung von mit Silicium-Kohlenstoff gebundenen aromatischen Gruppen enthaltenden Polysiloxanen |
-
1998
- 1998-02-09 JP JP53620798A patent/JP2001512511A/ja not_active Ceased
- 1998-02-09 AU AU63964/98A patent/AU6396498A/en not_active Abandoned
- 1998-02-09 EP EP98909423A patent/EP0963397A1/de not_active Withdrawn
- 1998-02-09 US US09/367,668 patent/US6258968B1/en not_active Expired - Fee Related
- 1998-02-09 WO PCT/EP1998/000700 patent/WO1998037126A1/de not_active Application Discontinuation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2714807A1 (de) * | 1976-04-08 | 1977-10-20 | Goldschmidt Ag Th | Verfahren zur herstellung aequilibrierter organopolysiloxangemische mit am silicium gebundenen organosulfonsaeuregruppen |
DE3112735A1 (de) * | 1980-04-04 | 1982-04-01 | General Electric Co., Schenectady, N.Y. | "als hydraulische fluessigkeit brauchbare silicon-fluessigkeit und verfahren zur kraftuebertragung" |
DE3334782A1 (de) * | 1983-04-19 | 1984-10-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polydiorganosiloxanen mit hydroxyaryloxy-endgruppen |
EP0317840A1 (de) * | 1987-11-25 | 1989-05-31 | General Electric Company | Katalysator zur Herstellung von Polyfluorosiloxanen |
EP0365938A2 (de) * | 1988-10-24 | 1990-05-02 | General Electric Company | Saure Equilibrierung von mit Silicium-Kohlenstoff gebundenen aromatischen Gruppen enthaltenden Polysiloxanen |
Also Published As
Publication number | Publication date |
---|---|
AU6396498A (en) | 1998-09-09 |
US6258968B1 (en) | 2001-07-10 |
EP0963397A1 (de) | 1999-12-15 |
JP2001512511A (ja) | 2001-08-21 |
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