JPS59124931A - フルオロアルキル基および／またはフルオロアルキルオキシアルキル基を有するジオルガノポリシロキサンの製法 - Google Patents
フルオロアルキル基および／またはフルオロアルキルオキシアルキル基を有するジオルガノポリシロキサンの製法Info
- Publication number
- JPS59124931A JPS59124931A JP58194440A JP19444083A JPS59124931A JP S59124931 A JPS59124931 A JP S59124931A JP 58194440 A JP58194440 A JP 58194440A JP 19444083 A JP19444083 A JP 19444083A JP S59124931 A JPS59124931 A JP S59124931A
- Authority
- JP
- Japan
- Prior art keywords
- group
- fluoroalkyl
- formula
- groups
- carbon atoms
- 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.)
- Granted
Links
- 125000003709 fluoroalkyl group Chemical group 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- -1 amine salts Chemical class 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 229920002545 silicone oil Polymers 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 150000003961 organosilicon compounds Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YYSFXUWWPNHNAZ-OSDRTFJJSA-N 851536-75-9 Chemical compound C1[C@@H](OC)[C@H](OCCOCC)CC[C@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CCC2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 YYSFXUWWPNHNAZ-OSDRTFJJSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000410518 Cyrano Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- MLRKYSNODSLPAB-UHFFFAOYSA-N hex-1-yn-1-ol Chemical group CCCCC#CO MLRKYSNODSLPAB-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010626 work up procedure Methods 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
- C08G77/06—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
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823248546 DE3248546A1 (de) | 1982-12-29 | 1982-12-29 | Verfahren zur herstellung von fluoralkylgruppen aufweisendem diorganopolysiloxan |
| DE3248546.8 | 1982-12-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59124931A true JPS59124931A (ja) | 1984-07-19 |
| JPS6110488B2 JPS6110488B2 (OSRAM) | 1986-03-29 |
Family
ID=6182101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58194440A Granted JPS59124931A (ja) | 1982-12-29 | 1983-10-19 | フルオロアルキル基および／またはフルオロアルキルオキシアルキル基を有するジオルガノポリシロキサンの製法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4577040A (OSRAM) |
| EP (1) | EP0113127B1 (OSRAM) |
| JP (1) | JPS59124931A (OSRAM) |
| AU (1) | AU562023B2 (OSRAM) |
| CA (1) | CA1234574A (OSRAM) |
| DE (2) | DE3248546A1 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63297429A (ja) * | 1987-05-29 | 1988-12-05 | Asahi Glass Co Ltd | 長鎖フルオロアルキル基含有シリコ−ンオイル |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3161780B2 (ja) * | 1991-09-30 | 2001-04-25 | 東レ・ダウコーニング・シリコーン株式会社 | α，ω−ジヒドロキシフルオロアルキルメチルポリシロキサンの製造方法 |
| JPH0616813A (ja) * | 1992-06-29 | 1994-01-25 | Toray Dow Corning Silicone Co Ltd | フルオロシリコ−ンポリマ−およびその製造方法 |
| US5853617A (en) * | 1997-05-14 | 1998-12-29 | Gallagher; Christopher T. | Method and composition for suppressing oil-based foams |
| US6291623B1 (en) * | 1999-10-12 | 2001-09-18 | University Of Southern California | Fluoroalkylsubstituted cyclotrisiloxanes, their use for preparation of new polymers and novel polymers |
| RU2268902C1 (ru) * | 2004-11-30 | 2006-01-27 | Федеральное государственное унитарное предприятие "Государственный научно-исследовательский институт химии и технологии элементоорганических соединений" (ФГУП ГНИИХТЭОС) | Способ получения олигометил-гамма-трифторпропилсилоксанов |
| US20080167390A1 (en) * | 2006-06-01 | 2008-07-10 | James Archer | Defoamer composition for suppressing oil-based and water-based foams |
| WO2010113188A1 (en) * | 2009-03-31 | 2010-10-07 | Maflon S.R.L. | Fluorurated siliconic polymer, synthesis method and use |
| EP3071678A1 (en) | 2013-11-20 | 2016-09-28 | Dow Corning Corporation | Organosiloxane compositions |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1165869B (de) * | 1964-03-19 | Elfriede Husemann Dr | Verfahren zur Herstellung von Polysiloxanen mit endstaendig ungesaettigten Gruppen | |
| FR1130089A (fr) * | 1954-05-11 | 1957-01-30 | Thomson Houston Comp Francaise | Catalyseurs fugaces pour la polymérisation des organopolysiloxanes |
| NL131011C (OSRAM) * | 1966-11-02 | |||
| US3661962A (en) * | 1969-05-09 | 1972-05-09 | Stauffer Wacker Silicone Corp | Molecular weight control and polysiloxanes |
| US3997496A (en) * | 1975-05-12 | 1976-12-14 | General Electric Company | Process for the preparation of fluorosilicone polymers and copolymers |
| US4028338A (en) * | 1975-10-09 | 1977-06-07 | General Electric Company | Fluorosiloxydiphenylsiloxy block copolymers |
| FR2353589A1 (fr) * | 1976-05-31 | 1977-12-30 | Rhone Poulenc Ind | Procede de preparation d'organopolysiloxanes |
| DE2834172A1 (de) * | 1978-08-04 | 1980-02-21 | Bayer Ag | Verfahren zur herstellung von fluoralkylhaltigen organopolysiloxanen |
-
1982
- 1982-12-29 DE DE19823248546 patent/DE3248546A1/de not_active Withdrawn
-
1983
- 1983-10-19 JP JP58194440A patent/JPS59124931A/ja active Granted
- 1983-11-16 US US06/552,578 patent/US4577040A/en not_active Expired - Fee Related
- 1983-11-25 CA CA000441992A patent/CA1234574A/en not_active Expired
- 1983-12-23 AU AU22903/83A patent/AU562023B2/en not_active Ceased
- 1983-12-29 DE DE8383113204T patent/DE3381292D1/de not_active Expired - Lifetime
- 1983-12-29 EP EP83113204A patent/EP0113127B1/de not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63297429A (ja) * | 1987-05-29 | 1988-12-05 | Asahi Glass Co Ltd | 長鎖フルオロアルキル基含有シリコ−ンオイル |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0113127B1 (de) | 1990-03-07 |
| AU2290383A (en) | 1984-07-05 |
| EP0113127A3 (en) | 1987-08-05 |
| JPS6110488B2 (OSRAM) | 1986-03-29 |
| CA1234574A (en) | 1988-03-29 |
| US4577040A (en) | 1986-03-18 |
| EP0113127A2 (de) | 1984-07-11 |
| DE3381292D1 (de) | 1990-04-12 |
| DE3248546A1 (de) | 1984-07-05 |
| AU562023B2 (en) | 1987-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3294737A (en) | Organopolysiloxanes | |
| RU2293745C2 (ru) | Способ образования полигедральных олигомерных силсесквиоксанов (варианты) | |
| US5220033A (en) | Siloxane compounds and their preparation | |
| US5028679A (en) | Method for preparing perfluoroalkyl group-containing organopolysiloxanes | |
| US5087720A (en) | Polysilethylenesiloxane | |
| US4311821A (en) | Process for the preparation of crosslinked organopoly-siloxanes and their use as active ingredient of abhesive coating materials for two-dimensional carriers | |
| EP0465263B1 (en) | Polysilethylenesiloxane | |
| CA2030958C (en) | Polydimethylsiloxane terminated at one end with a branched aminoalkyl group and preparation thereof | |
| JPS59124931A (ja) | フルオロアルキル基および／またはフルオロアルキルオキシアルキル基を有するジオルガノポリシロキサンの製法 | |
| JPS5919118B2 (ja) | オクタフェニルシクロテトラシロキサンの製法 | |
| US5177157A (en) | Process for preparing a silicone resin-modified phenolic resin | |
| JP3506358B2 (ja) | 分枝型シリコーンオイルの製造方法 | |
| US4273907A (en) | Benzoin-bonded organopolysiloxanes and method for the preparation thereof | |
| US5254658A (en) | Method for the preparation of branched organopolysiloxane | |
| US3963744A (en) | Silicone-compatible phthalocyanine dyestuffs | |
| US5350824A (en) | Fluorosilicone polymers and methods for the preparation thereof | |
| JPH05117393A (ja) | 分岐ポリオルガノポリシロキサン | |
| US5233005A (en) | Method for preparing alpha, omega-dihydroxyperfluoroalkylethylmethylpolysiloxanes | |
| JPH0739426B2 (ja) | アシルアミノオルガノシリコーン化合物の製造方法 | |
| US5087683A (en) | Process for producing α, ω-hydroxyfluoroalkylpolysiloxanes | |
| US5210249A (en) | Organosilicon compounds containing s-alkylthiosulfate groups, processes for their preparation and use of the same | |
| US3965134A (en) | Process for making silarylenesilanediol | |
| JP3229394B2 (ja) | 両末端エポキシ基封鎖ジフェニルシロキシ単位含有ジオルガノポリシロキサンの製造方法 | |
| JPS5932515B2 (ja) | ウレタン樹脂用離型剤 | |
| EP0693520A1 (en) | Method for the preparation of organopolysiloxanes |