CZ299389B6 - Nové fluoralkylsubstituované cyklotrisiloxany, jejich použití pro prípravu nových polymeru a nové polymery - Google Patents
Nové fluoralkylsubstituované cyklotrisiloxany, jejich použití pro prípravu nových polymeru a nové polymery Download PDFInfo
- Publication number
- CZ299389B6 CZ299389B6 CZ20021273A CZ20021273A CZ299389B6 CZ 299389 B6 CZ299389 B6 CZ 299389B6 CZ 20021273 A CZ20021273 A CZ 20021273A CZ 20021273 A CZ20021273 A CZ 20021273A CZ 299389 B6 CZ299389 B6 CZ 299389B6
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- CZ
- Czechia
- Prior art keywords
- substituents
- novel
- polymerization
- formula
- nmr
- Prior art date
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- JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical class O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 125000003709 fluoroalkyl group Chemical group 0.000 title abstract description 4
- 229920000642 polymer Polymers 0.000 title description 10
- 229920001519 homopolymer Polymers 0.000 claims abstract description 10
- 229920001400 block copolymer Polymers 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- -1 lithium diphenylsilanolate Chemical compound 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 10
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 230000001788 irregular Effects 0.000 claims description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- DALSQVVNXWQJCS-UHFFFAOYSA-N [Li+].[Li+].C[SiH](C)O[Si](C)(C)[O-].C[SiH](C)O[Si](C)(C)[O-] Chemical compound [Li+].[Li+].C[SiH](C)O[Si](C)(C)[O-].C[SiH](C)O[Si](C)(C)[O-] DALSQVVNXWQJCS-UHFFFAOYSA-N 0.000 claims description 3
- UCVHTYKWNMPBGD-UHFFFAOYSA-N dilithium oxido(diphenyl)silane Chemical group [Li+].[Li+].[O-][SiH](c1ccccc1)c1ccccc1.[O-][SiH](c1ccccc1)c1ccccc1 UCVHTYKWNMPBGD-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229920005604 random copolymer Polymers 0.000 abstract 2
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 3
- 238000006459 hydrosilylation reaction Methods 0.000 description 3
- 239000005048 methyldichlorosilane Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- LVJZCPNIJXVIAT-UHFFFAOYSA-N 1-ethenyl-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(C=C)C(F)=C1F LVJZCPNIJXVIAT-UHFFFAOYSA-N 0.000 description 2
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 2
- VFUGMTAIQWBRCM-UHFFFAOYSA-N dihydroxy-methyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(O)O VFUGMTAIQWBRCM-UHFFFAOYSA-N 0.000 description 2
- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229960004624 perflexane Drugs 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FYQFWFHDPNXORA-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C FYQFWFHDPNXORA-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 238000012653 anionic ring-opening polymerization Methods 0.000 description 1
- FSIJKGMIQTVTNP-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C=C)C=C FSIJKGMIQTVTNP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012656 cationic ring opening polymerization Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- RUWVYOFYCWPDMF-UHFFFAOYSA-N dichloro-bis(3,3,3-trifluoropropyl)silane Chemical compound FC(F)(F)CC[Si](Cl)(Cl)CCC(F)(F)F RUWVYOFYCWPDMF-UHFFFAOYSA-N 0.000 description 1
- OHABWQNEJUUFAV-UHFFFAOYSA-N dichloro-methyl-(3,3,3-trifluoropropyl)silane Chemical compound C[Si](Cl)(Cl)CCC(F)(F)F OHABWQNEJUUFAV-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 101150023613 mev-1 gene Proteins 0.000 description 1
- 238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 1
- 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 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- YOIAWAIKYVEKMF-UHFFFAOYSA-N trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F YOIAWAIKYVEKMF-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/416,266 US6291623B1 (en) | 1999-10-12 | 1999-10-12 | Fluoroalkylsubstituted cyclotrisiloxanes, their use for preparation of new polymers and novel polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ20021273A3 CZ20021273A3 (cs) | 2002-09-11 |
| CZ299389B6 true CZ299389B6 (cs) | 2008-07-09 |
Family
ID=23649267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20021273A CZ299389B6 (cs) | 1999-10-12 | 2000-10-05 | Nové fluoralkylsubstituované cyklotrisiloxany, jejich použití pro prípravu nových polymeru a nové polymery |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6291623B1 (enExample) |
| EP (1) | EP1220860B1 (enExample) |
| JP (1) | JP2003511519A (enExample) |
| KR (1) | KR100684549B1 (enExample) |
| CN (1) | CN1152883C (enExample) |
| AT (1) | ATE277057T1 (enExample) |
| AU (1) | AU780592B2 (enExample) |
| CA (1) | CA2386327C (enExample) |
| CZ (1) | CZ299389B6 (enExample) |
| DE (2) | DE60014129T2 (enExample) |
| DK (1) | DK1220860T3 (enExample) |
| EE (1) | EE05066B1 (enExample) |
| ES (1) | ES2226929T3 (enExample) |
| HK (1) | HK1047108B (enExample) |
| HU (1) | HUP0203324A3 (enExample) |
| IL (1) | IL148856A (enExample) |
| MX (1) | MXPA02003410A (enExample) |
| NO (1) | NO20021703D0 (enExample) |
| PL (1) | PL196170B1 (enExample) |
| RU (1) | RU2230747C2 (enExample) |
| SK (1) | SK286506B6 (enExample) |
| TW (1) | TW506980B (enExample) |
| UA (1) | UA73958C2 (enExample) |
| WO (1) | WO2001027121A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004016670A2 (en) * | 2002-08-16 | 2004-02-26 | The University Of Akron | Poly(cyclosiloxane) composiiton and method of synthesis thereof |
| US20060293483A1 (en) * | 2005-06-27 | 2006-12-28 | General Electric Co,Mpmany | Fluoro-silicone copolymers |
| WO2007002767A1 (en) * | 2005-06-27 | 2007-01-04 | Momentive Performance Materials Inc. | Methods of making high fluorine content fluoro-silicone copolymers |
| US20080145552A1 (en) * | 2006-12-15 | 2008-06-19 | Mia Genevieve Berrettini | Fluorochemical and polyoxyalkylene siloxane additive for coatings |
| US7723414B2 (en) | 2006-12-22 | 2010-05-25 | E. I. Du Pont De Nemours And Company | Antistatic system for polymers |
| RU2402577C2 (ru) * | 2008-11-05 | 2010-10-27 | Виталий Абрамович Кормер | Способ получения циклотрисилоксанов |
| RU2563253C1 (ru) * | 2014-09-30 | 2015-09-20 | Федеральное государственное унитарное предприятие "Ордена Ленина и ордена Трудового Красного Знамени научно-исследовательский институт синтетического каучука имени академика С.В. Лебедева" (ФГУП "НИИСК") | Силоксановые блоксополимеры, содержащие метил (гексафторалкил) силоксановые звенья |
| US9359386B1 (en) * | 2015-02-19 | 2016-06-07 | Gelest Technologies, Inc. | Silanes and silicones with distinct hydrophilic and oleophobic substitution |
| CN107636047A (zh) * | 2015-05-18 | 2018-01-26 | 美利肯公司 | 环状硅氧烷化合物以及包含其的组合物 |
| CN110156826B (zh) * | 2019-06-20 | 2021-08-31 | 威海新元化工有限公司 | 二苯基环三硅氧烷及其制备方法与应用 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3070619A (en) * | 1953-10-19 | 1962-12-25 | Union Carbide Corp | Production of 2-mercapto-2-thiono-derivatives of heterocyclic phosphoruscontaining compounds |
| US4814418A (en) * | 1986-08-08 | 1989-03-21 | Asahi Glass Company, Ltd. | Fluorosilicone polymer, processes for the production thereof and composition containing it |
| EP0563902A1 (en) * | 1992-03-31 | 1993-10-06 | Dow Corning Toray Silicone Company, Limited | Fluorosilicone block copolymers and method for the preparation thereof |
| WO1997020851A1 (en) * | 1995-12-07 | 1997-06-12 | Bausch & Lomb Incorporated | Monomeric units useful for reducing the modulus of low water polymeric silicone compositions |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3070617A (en) * | 1957-09-09 | 1962-12-25 | Dow Corning | Cyclic bistrifluoropropyl siloxanes |
| US3364244A (en) | 1964-07-01 | 1968-01-16 | Gen Electric | Cyclic siloxanes |
| US3590064A (en) * | 1969-07-23 | 1971-06-29 | Charles W Lacefield | Process for preparing cyclosiloxanes |
| DE3248546A1 (de) * | 1982-12-29 | 1984-07-05 | Wacker-Chemie GmbH, 8000 München | Verfahren zur herstellung von fluoralkylgruppen aufweisendem diorganopolysiloxan |
| US4587320A (en) * | 1984-12-21 | 1986-05-06 | Dow Corning Corporation | Method for making carboxyfunctional silicone glycols |
| EP0191543A1 (en) * | 1985-01-15 | 1986-08-20 | Ventec Laboratories, Inc. | Silicone insect toxicants |
| 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 |
| JP2849037B2 (ja) * | 1993-02-15 | 1999-01-20 | 信越化学工業株式会社 | 鎖状ポリオルガノシロキサン及びその製造方法 |
| JPH06321968A (ja) * | 1993-05-14 | 1994-11-22 | Shin Etsu Chem Co Ltd | シクロトリシロキサンの製造方法 |
| JP3473871B2 (ja) * | 1994-12-28 | 2003-12-08 | 信越化学工業株式会社 | オルガノポリシロキサンの製造方法 |
| JPH08239479A (ja) * | 1995-03-02 | 1996-09-17 | Shin Etsu Chem Co Ltd | 単分散オルガノポリシロキサンの製造方法 |
-
1999
- 1999-10-12 US US09/416,266 patent/US6291623B1/en not_active Expired - Fee Related
-
2000
- 2000-05-10 UA UA2002053848A patent/UA73958C2/uk unknown
- 2000-10-05 ES ES00967924T patent/ES2226929T3/es not_active Expired - Lifetime
- 2000-10-05 PL PL354357A patent/PL196170B1/pl not_active IP Right Cessation
- 2000-10-05 HU HU0203324A patent/HUP0203324A3/hu unknown
- 2000-10-05 IL IL14885600A patent/IL148856A/xx not_active IP Right Cessation
- 2000-10-05 CZ CZ20021273A patent/CZ299389B6/cs not_active IP Right Cessation
- 2000-10-05 HK HK02108788.7A patent/HK1047108B/en not_active IP Right Cessation
- 2000-10-05 DE DE60014129T patent/DE60014129T2/de not_active Expired - Lifetime
- 2000-10-05 DK DK00967924T patent/DK1220860T3/da active
- 2000-10-05 AU AU77914/00A patent/AU780592B2/en not_active Ceased
- 2000-10-05 DE DE1220860T patent/DE1220860T1/de active Pending
- 2000-10-05 WO PCT/FI2000/000858 patent/WO2001027121A1/en not_active Ceased
- 2000-10-05 CN CNB00814060XA patent/CN1152883C/zh not_active Expired - Fee Related
- 2000-10-05 MX MXPA02003410A patent/MXPA02003410A/es active IP Right Grant
- 2000-10-05 CA CA002386327A patent/CA2386327C/en not_active Expired - Fee Related
- 2000-10-05 EP EP00967924A patent/EP1220860B1/en not_active Expired - Lifetime
- 2000-10-05 JP JP2001530339A patent/JP2003511519A/ja active Pending
- 2000-10-05 SK SK419-2002A patent/SK286506B6/sk not_active IP Right Cessation
- 2000-10-05 RU RU2002112329/04A patent/RU2230747C2/ru not_active IP Right Cessation
- 2000-10-05 KR KR1020027004654A patent/KR100684549B1/ko not_active Expired - Fee Related
- 2000-10-05 EE EEP200200187A patent/EE05066B1/xx not_active IP Right Cessation
- 2000-10-05 AT AT00967924T patent/ATE277057T1/de not_active IP Right Cessation
- 2000-10-09 TW TW089121108A patent/TW506980B/zh not_active IP Right Cessation
-
2002
- 2002-04-11 NO NO20021703A patent/NO20021703D0/no not_active Application Discontinuation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3070619A (en) * | 1953-10-19 | 1962-12-25 | Union Carbide Corp | Production of 2-mercapto-2-thiono-derivatives of heterocyclic phosphoruscontaining compounds |
| US4814418A (en) * | 1986-08-08 | 1989-03-21 | Asahi Glass Company, Ltd. | Fluorosilicone polymer, processes for the production thereof and composition containing it |
| EP0563902A1 (en) * | 1992-03-31 | 1993-10-06 | Dow Corning Toray Silicone Company, Limited | Fluorosilicone block copolymers and method for the preparation thereof |
| WO1997020851A1 (en) * | 1995-12-07 | 1997-06-12 | Bausch & Lomb Incorporated | Monomeric units useful for reducing the modulus of low water polymeric silicone compositions |
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