CA1333115C - Process for preparing organopolysiloxanes containing sic-bonded organic radicals having a basic nitrogen - Google Patents
Process for preparing organopolysiloxanes containing sic-bonded organic radicals having a basic nitrogenInfo
- Publication number
- CA1333115C CA1333115C CA000550908A CA550908A CA1333115C CA 1333115 C CA1333115 C CA 1333115C CA 000550908 A CA000550908 A CA 000550908A CA 550908 A CA550908 A CA 550908A CA 1333115 C CA1333115 C CA 1333115C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- organopolysiloxane
- radicals
- radical
- integer
- 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.)
- Expired - Fee Related
Links
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 229910052757 nitrogen Inorganic materials 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- -1 alkyl radicals Chemical class 0.000 claims abstract description 50
- 150000003254 radicals Chemical class 0.000 claims abstract description 37
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 16
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 16
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910000077 silane Inorganic materials 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 10
- 125000000962 organic group Chemical group 0.000 claims abstract description 8
- 125000005372 silanol group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 8
- 239000000413 hydrolysate Substances 0.000 claims description 5
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 238000009833 condensation Methods 0.000 abstract description 8
- 230000005494 condensation Effects 0.000 abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 9
- 125000001453 quaternary ammonium group Chemical group 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 150000003961 organosilicon compounds Chemical class 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 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 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 206010059837 Adhesion Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MMRXGMFYRAWUAC-UHFFFAOYSA-N O[SiH3].P Chemical group O[SiH3].P MMRXGMFYRAWUAC-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- HBCDKMARZSDTLB-UHFFFAOYSA-N [K+].C[SiH2][O-] Chemical compound [K+].C[SiH2][O-] HBCDKMARZSDTLB-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IJJSYKQZFFGIEE-UHFFFAOYSA-N naphthalene;potassium Chemical compound [K].C1=CC=CC2=CC=CC=C21 IJJSYKQZFFGIEE-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical group O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ONQCKWIDZTZEJA-UHFFFAOYSA-N sodium;pentane Chemical compound [Na+].CCCC[CH2-] ONQCKWIDZTZEJA-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08G77/22—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
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)
- Jellies, Jams, And Syrups (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3637837.2 | 1986-11-06 | ||
| DE19863637837 DE3637837A1 (de) | 1986-11-06 | 1986-11-06 | Verfahren zur herstellung von organopolysiloxanen mit basischen stickstoff aufweisenden, sic-gebundenen organischen resten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1333115C true CA1333115C (en) | 1994-11-15 |
Family
ID=6313308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000550908A Expired - Fee Related CA1333115C (en) | 1986-11-06 | 1987-11-03 | Process for preparing organopolysiloxanes containing sic-bonded organic radicals having a basic nitrogen |
Country Status (8)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3808200A1 (de) * | 1988-03-11 | 1989-09-21 | Wacker Chemie Gmbh | Bei raumtemperatur zu anstrichvertraeglichen bis ueberstreichbaren elastomeren vernetzende organopolysiloxanmassen |
| JP2799637B2 (ja) * | 1991-02-27 | 1998-09-21 | 信越化学工業株式会社 | 高分子量オルガノポリシロキサンの製造方法 |
| DE4208447C1 (en) * | 1992-03-17 | 1993-06-03 | Th. Goldschmidt Ag, 4300 Essen, De | Silicone(s) with silicon-carbon linked residues contg. basic N and alkoxy gps. - by reacting silicone(s) contg. hydroxy-alkyl gps. with amino:alkyl-alkoxy-silane(s) in presence of non-equilibrating acid catalyst |
| FR2714402B1 (fr) * | 1993-12-27 | 1996-02-02 | Rhone Poulenc Chimie | Procédé d'adoucissage textile non jaunissant dans lequel on utilise une composition comprenant un polyorganosiloxane. |
| DE19649183A1 (de) * | 1996-11-27 | 1998-06-04 | Fraunhofer Ges Forschung | Antistatikmittel, Verfahren zu dessen Herstellung und dessen Verwendung zur Herstellung von antistatischen Beschichtungen |
| EP0927735A1 (de) * | 1998-01-02 | 1999-07-07 | Hüls Aktiengesellschaft | Verfahren zur Herstellung von nichtreaktiven Aminosiliconölen |
| JP4399066B2 (ja) * | 1999-10-29 | 2010-01-13 | 東レ・ダウコーニング株式会社 | アミノ基含有オルガノポリシロキサンの製造方法 |
| RU2219453C2 (ru) * | 2002-01-22 | 2003-12-20 | Государственный научный центр РФ "Научно-исследовательский институт атомных реакторов" | Вакуум-контейнер для расплавленных солей |
| WO2005105970A1 (en) * | 2004-04-16 | 2005-11-10 | The Procter & Gamble Company | Liquid laundry detergent compositions with silicone blends as fabric care agents |
| DE102007020569A1 (de) * | 2007-05-02 | 2008-11-06 | Wacker Chemie Ag | Verfahren zur Herstellung von Aminoalkylpolysiloxanen |
| DE102007020568A1 (de) * | 2007-05-02 | 2008-11-06 | Wacker Chemie Ag | Verfahren zur kontinuierlichen Herstellung von Aminoalkylgruppen aufweisenden Organopolysiloxanen |
| DE102007036069A1 (de) * | 2007-08-01 | 2009-02-05 | Wacker Chemie Ag | Mehrstufiges Verfahren zur Herstellung von Aminoalkylgruppen aufweisenden Organopolysiloxanen |
| KR101677255B1 (ko) * | 2015-03-25 | 2016-11-17 | 건솔루션(주) | 공작물 위치 자동 인식 장치 및 그 방법 |
| DE102020118717B4 (de) | 2020-07-15 | 2024-02-08 | Humbaur Gmbh | Zurrvorrichtung für ein Nutzfahrzeug, Nutzfahrzeug mit einer solchen Zurrvorrichtung und Herstellungsverfahren |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2947771A (en) * | 1956-10-12 | 1960-08-02 | Union Carbide Corp | Aminoalkylpolysiloxanes and process for their production |
| DE1120145B (de) * | 1956-10-12 | 1961-12-21 | Union Carbide Corp | Verfahren zur Herstellung von endblockierten Organopolysiloxanen |
| US2921950A (en) * | 1957-08-15 | 1960-01-19 | Union Carbide Corp | Method for preparing copolymeric organopolysiloxanes |
| JPS5629691B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-08-11 | 1981-07-10 | ||
| US4496705A (en) * | 1984-01-04 | 1985-01-29 | General Electric Company | Synthesis of zwitterionic siloxane polymers |
| DE3523206A1 (de) * | 1985-06-28 | 1987-01-02 | Bayer Ag | Verfahren zur herstellung von poly(diorganosiloxanen) mit alkoxyendgruppen |
| US4661577A (en) * | 1985-10-01 | 1987-04-28 | General Electric Company | Aminofunctional polysiloxanes |
| JP2588724B2 (ja) * | 1987-09-08 | 1997-03-12 | 東レ・ダウコーニング・シリコーン株式会社 | 分子鎖中央の側鎖にアルケニル基を有するオルガノポリシロキサンの製造方法 |
| DE3742069A1 (de) * | 1987-12-11 | 1989-06-22 | Wacker Chemie Gmbh | Verfahren zur herstellung von diorganopolysiloxanen mit triorganosiloxygruppen als endstaendigen einheiten |
-
1986
- 1986-11-06 DE DE19863637837 patent/DE3637837A1/de not_active Withdrawn
-
1987
- 1987-11-02 DE DE8787116116T patent/DE3786443D1/de not_active Expired - Fee Related
- 1987-11-02 ES ES87116116T patent/ES2056806T3/es not_active Expired - Lifetime
- 1987-11-02 EP EP87116116A patent/EP0269886B1/de not_active Expired - Lifetime
- 1987-11-02 AT AT87116116T patent/ATE91294T1/de not_active IP Right Cessation
- 1987-11-03 CA CA000550908A patent/CA1333115C/en not_active Expired - Fee Related
- 1987-11-05 AU AU80808/87A patent/AU590993B2/en not_active Ceased
- 1987-11-05 BR BR8705951A patent/BR8705951A/pt not_active IP Right Cessation
- 1987-11-05 JP JP62278415A patent/JPS63135427A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63135427A (ja) | 1988-06-07 |
| EP0269886B1 (de) | 1993-07-07 |
| AU590993B2 (en) | 1989-11-23 |
| ES2056806T3 (es) | 1994-10-16 |
| JPH0238604B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-08-31 |
| DE3637837A1 (de) | 1988-05-19 |
| EP0269886A3 (en) | 1990-05-02 |
| DE3786443D1 (de) | 1993-08-12 |
| BR8705951A (pt) | 1988-06-14 |
| AU8080887A (en) | 1988-05-12 |
| EP0269886A2 (de) | 1988-06-08 |
| ATE91294T1 (de) | 1993-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |