EP0963397A1 - Procede de production de siloxanes organofonctionnels et leur utilisation - Google Patents
Procede de production de siloxanes organofonctionnels et leur utilisationInfo
- Publication number
- EP0963397A1 EP0963397A1 EP98909423A EP98909423A EP0963397A1 EP 0963397 A1 EP0963397 A1 EP 0963397A1 EP 98909423 A EP98909423 A EP 98909423A EP 98909423 A EP98909423 A EP 98909423A EP 0963397 A1 EP0963397 A1 EP 0963397A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- dialkylsiloxane
- catalyst
- sio
- compound
- 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.)
- Withdrawn
Links
- -1 siloxanes Chemical class 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 239000008096 xylene Substances 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 230000002209 hydrophobic effect Effects 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 238000011067 equilibration Methods 0.000 claims description 3
- 229920000620 organic polymer Polymers 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 238000010992 reflux Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 10
- 229920001296 polysiloxane Polymers 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000006386 neutralization reaction Methods 0.000 description 7
- 239000000470 constituent Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000001103 potassium chloride Substances 0.000 description 5
- 235000011164 potassium chloride Nutrition 0.000 description 5
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000011010 flushing procedure Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000004611 spectroscopical analysis Methods 0.000 description 4
- 239000005051 trimethylchlorosilane Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229910003849 O-Si Inorganic materials 0.000 description 3
- 229910003872 O—Si Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910020175 SiOH Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- SSRHZSLSLDOUJB-UHFFFAOYSA-N benzene-1,4-diol;toluene Chemical compound CC1=CC=CC=C1.OC1=CC=C(O)C=C1 SSRHZSLSLDOUJB-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000005028 dihydroxyaryl group Chemical group 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- CDPRIDXQDFRFSG-UHFFFAOYSA-N pent-2-ene-1,2-diol Chemical compound CCC=C(O)CO CDPRIDXQDFRFSG-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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
L'invention concerne un procédé de production de siloxanes organofonctionnels liés à Si-O-C et leur utilisation.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19706646 | 1997-02-20 | ||
| DE19706646 | 1997-02-20 | ||
| PCT/EP1998/000700 WO1998037126A1 (fr) | 1997-02-20 | 1998-02-09 | Procede de production de siloxanes organofonctionnels et leur utilisation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0963397A1 true EP0963397A1 (fr) | 1999-12-15 |
Family
ID=7820891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP98909423A Withdrawn EP0963397A1 (fr) | 1997-02-20 | 1998-02-09 | Procede de production de siloxanes organofonctionnels et leur utilisation |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6258968B1 (fr) |
| EP (1) | EP0963397A1 (fr) |
| JP (1) | JP2001512511A (fr) |
| AU (1) | AU6396498A (fr) |
| WO (1) | WO1998037126A1 (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6482912B2 (en) * | 2001-01-29 | 2002-11-19 | Ndsu Research Foundation | Method of preparing aminofunctional alkoxy polysiloxanes |
| US7449537B2 (en) * | 2001-01-29 | 2008-11-11 | Ndsu Research Foundation | Antineoplastic polyalkoxyalkylsiloxanes and methods of use thereof |
| CN102775757B (zh) * | 2007-01-10 | 2015-05-27 | 沙特基础全球技术有限公司 | 低烟气密度聚(亚芳基醚)组合物,方法,和制品 |
| WO2012158767A1 (fr) | 2011-05-17 | 2012-11-22 | Momentive Performance Materials Gmbh | Copolymères polysiloxane-polyorgano séquencés |
| RU2014145007A (ru) * | 2012-04-10 | 2016-05-27 | Моментив Перформанс Матириалз Гмбх | Способ получения функциональных силоксанов с регулируемой структурой |
| JP6602300B2 (ja) | 2013-08-23 | 2019-11-06 | モーメンティブ・パフォーマンス・マテリアルズ・インク | シロキサン合成用触媒 |
| KR102257689B1 (ko) * | 2013-10-08 | 2021-05-31 | 코베스트로 도이칠란트 아게 | 폴리실록산-폴리카보네이트 블록 공축합물 |
| US9828463B2 (en) * | 2013-10-08 | 2017-11-28 | Covestro Deutschland Ag | Process for preparing polysiloxane-polycarbonate block cocondensates using a salt of a weak acid |
| US9845378B2 (en) * | 2013-10-08 | 2017-12-19 | Covestro Deutschland Ag | Process for preparing polysiloxane-polycarbonate block cocondensates |
| US9828462B2 (en) * | 2013-10-08 | 2017-11-28 | Covestro Deutschland Ag | Preparation of siloxane-containing block copolycarbonates by means of reactive extrusion |
| JP2017520663A (ja) | 2014-07-03 | 2017-07-27 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッド | エステル官能性ポリシロキサンおよびそれから作られるコポリマー |
| TWI894358B (zh) * | 2020-09-23 | 2025-08-21 | 日商三菱瓦斯化學股份有限公司 | 組成物及使用其之矽氧烷系熱塑性樹脂，及該等之製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1542963A (en) * | 1976-04-08 | 1979-03-28 | Goldschmidt Ag Th | Process for the manufacture of equilibrated mixtures of organopolysiloxanes having organo-sulphonate groups bonded to the silicon |
| AU6904781A (en) | 1980-04-04 | 1981-10-08 | General Electric Company | Silicone brake fluid |
| DE3334782A1 (de) | 1983-04-19 | 1984-10-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polydiorganosiloxanen mit hydroxyaryloxy-endgruppen |
| US4897459A (en) | 1987-11-25 | 1990-01-30 | General Electric Company | Catalyst for producing fluorosilicone polymers |
| US4895968A (en) | 1988-10-24 | 1990-01-23 | General Electric Company | Acid equilibration method for organcpolysiloxanes having carbon-silicon-bonded aromatic organic radicals |
-
1998
- 1998-02-09 EP EP98909423A patent/EP0963397A1/fr not_active Withdrawn
- 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 WO PCT/EP1998/000700 patent/WO1998037126A1/fr not_active Ceased
- 1998-02-09 US US09/367,668 patent/US6258968B1/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9837126A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001512511A (ja) | 2001-08-21 |
| WO1998037126A1 (fr) | 1998-08-27 |
| US6258968B1 (en) | 2001-07-10 |
| AU6396498A (en) | 1998-09-09 |
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