JPS6033846B2 - シリコーン共重合体とその製法 - Google Patents
シリコーン共重合体とその製法Info
- Publication number
- JPS6033846B2 JPS6033846B2 JP51120455A JP12045576A JPS6033846B2 JP S6033846 B2 JPS6033846 B2 JP S6033846B2 JP 51120455 A JP51120455 A JP 51120455A JP 12045576 A JP12045576 A JP 12045576A JP S6033846 B2 JPS6033846 B2 JP S6033846B2
- Authority
- JP
- Japan
- Prior art keywords
- block copolymer
- reaction
- solvent
- formula
- group
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 229920001296 polysiloxane Polymers 0.000 title description 2
- 229920001400 block copolymer Polymers 0.000 claims description 57
- 239000002904 solvent Substances 0.000 claims description 53
- 238000006243 chemical reaction Methods 0.000 claims description 36
- -1 aliphatic alcohols Chemical class 0.000 claims description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 24
- 239000013638 trimer Substances 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000003472 neutralizing effect Effects 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000006267 biphenyl group Chemical group 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 3
- 229940117389 dichlorobenzene Drugs 0.000 claims description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- OFXSXYCSPVKZPF-UHFFFAOYSA-N methoxyperoxymethane Chemical compound COOOC OFXSXYCSPVKZPF-UHFFFAOYSA-N 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- URZHQOCYXDNFGN-UHFFFAOYSA-N 2,4,6-trimethyl-2,4,6-tris(3,3,3-trifluoropropyl)-1,3,5,2,4,6-trioxatrisilinane Chemical compound FC(F)(F)CC[Si]1(C)O[Si](C)(CCC(F)(F)F)O[Si](C)(CCC(F)(F)F)O1 URZHQOCYXDNFGN-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 22
- 229920001577 copolymer Polymers 0.000 description 15
- 125000004122 cyclic group Chemical group 0.000 description 11
- 229920001971 elastomer Polymers 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 229920002379 silicone rubber Polymers 0.000 description 11
- 229920001187 thermosetting polymer Polymers 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000004945 silicone rubber Substances 0.000 description 9
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 239000005060 rubber Substances 0.000 description 6
- 239000000806 elastomer Substances 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000006057 Non-nutritive feed additive Substances 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 239000012763 reinforcing filler Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- COSWCAGTKRUTQV-UHFFFAOYSA-N 1,1,3-trimethylurea Chemical compound CNC(=O)N(C)C COSWCAGTKRUTQV-UHFFFAOYSA-N 0.000 description 1
- VCYDUTCMKSROID-UHFFFAOYSA-N 2,2,4,4,6,6-hexakis-phenyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound O1[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si]1(C=1C=CC=CC=1)C1=CC=CC=C1 VCYDUTCMKSROID-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 241000206761 Bacillariophyta Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- SZKKRCSOSQAJDE-UHFFFAOYSA-N Schradan Chemical group CN(C)P(=O)(N(C)C)OP(=O)(N(C)C)N(C)C SZKKRCSOSQAJDE-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 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 1
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- RSNQKPMXXVDJFG-UHFFFAOYSA-N tetrasiloxane Chemical compound [SiH3]O[SiH2]O[SiH2]O[SiH3] RSNQKPMXXVDJFG-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011282 treatment Methods 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
-
- 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
- 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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
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 |
|---|---|---|---|
| US05/621,032 US4028338A (en) | 1975-10-09 | 1975-10-09 | Fluorosiloxydiphenylsiloxy block copolymers |
| US621032 | 1975-10-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5256200A JPS5256200A (en) | 1977-05-09 |
| JPS6033846B2 true JPS6033846B2 (ja) | 1985-08-05 |
Family
ID=24488443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51120455A Expired JPS6033846B2 (ja) | 1975-10-09 | 1976-10-08 | シリコーン共重合体とその製法 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US4028338A (Direct) |
| JP (1) | JPS6033846B2 (Direct) |
| DE (1) | DE2645298A1 (Direct) |
| FR (1) | FR2327272A1 (Direct) |
| GB (1) | GB1558816A (Direct) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2353589A1 (fr) * | 1976-05-31 | 1977-12-30 | Rhone Poulenc Ind | Procede de preparation d'organopolysiloxanes |
| US4317899A (en) * | 1978-11-13 | 1982-03-02 | General Electric Company | Process for producing fluorosilicone polymers |
| JPS5628219A (en) * | 1979-08-17 | 1981-03-19 | Asahi Glass Co Ltd | New fluorine-containing elastomer |
| US4348531A (en) * | 1979-08-30 | 1982-09-07 | General Electric Company | Fluorosilicone polydimethylsiloxane equilibration chainstopper and process for manufacture |
| US4287353A (en) * | 1979-11-09 | 1981-09-01 | General Electric Company | Process for synthesizing silanol chain-stopped fluorosiloxane fluids |
| DE3106186A1 (de) * | 1981-02-19 | 1982-09-09 | Wacker-Chemie GmbH, 8000 München | Verfahren zur herstellung von organopolysiloxanen und verwendung dieser organop |
| DE3248546A1 (de) * | 1982-12-29 | 1984-07-05 | Wacker-Chemie GmbH, 8000 München | Verfahren zur herstellung von fluoralkylgruppen aufweisendem diorganopolysiloxan |
| US4525528A (en) * | 1983-10-11 | 1985-06-25 | General Electric Company | Peroxide-curable fluorosilicone copolymer compositions |
| US4736048A (en) * | 1986-06-04 | 1988-04-05 | Dow Corning Corporation | Pressure sensitive adhesive release liner and fluorosilicone compounds, compositions and method therefor |
| EP0255957A3 (en) * | 1986-08-08 | 1988-11-17 | Asahi Glass Company Ltd. | Fluorosilicone polymer, processes for the production thereof and composition containing it |
| JP2617191B2 (ja) * | 1986-08-22 | 1997-06-04 | 旭硝子株式会社 | 架橋可能なフルオロシリコーン重合体の製造方法 |
| 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 |
| JP2842443B2 (ja) * | 1988-09-30 | 1999-01-06 | 東レ・ダウコーニング・シリコーン株式会社 | 片方の末端に重合性官能基を有するオルガノポリシロキサンの製造方法 |
| US5087683A (en) * | 1989-02-07 | 1992-02-11 | Shin-Etsu Chemical Co. Ltd. | Process for producing α, ω-hydroxyfluoroalkylpolysiloxanes |
| JPH05279481A (ja) * | 1992-03-31 | 1993-10-26 | Toray Dow Corning Silicone Co Ltd | フルオロシリコ−ンブロック共重合体およびその製造方法 |
| GB2278846B (en) * | 1993-06-10 | 1997-04-16 | Gen Electric | Fluorosilicone terpolymeric fluid |
| US6451954B1 (en) * | 2000-07-27 | 2002-09-17 | General Electric Company | Copolymer sealant compositions and method for making |
| JP2004523606A (ja) * | 2000-12-14 | 2004-08-05 | ゼネラル・エレクトリック・カンパニイ | フルオロシリコーン消泡剤組成物の製造方法 |
| WO2006043334A1 (ja) * | 2004-10-18 | 2006-04-27 | Nippon Koyu Ltd. | 放熱用シリコーン組成物 |
| CN100469818C (zh) * | 2005-12-07 | 2009-03-18 | 司林旭 | 氟硅弹性体的制备方法 |
| JP5278242B2 (ja) * | 2009-08-14 | 2013-09-04 | 信越化学工業株式会社 | 分子鎖両末端トリオルガノシロキシ基封鎖オルガノポリシロキサンの製造方法 |
| KR20160088894A (ko) | 2013-11-20 | 2016-07-26 | 다우 코닝 코포레이션 | 유기실록산 조성물 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2800494A (en) * | 1954-10-22 | 1957-07-23 | Dow Corning | Unsaturated fluorocarbon silanes and their hydrolysis products |
| NL286867A (Direct) * | 1961-12-18 | 1900-01-01 | ||
| BE635643A (Direct) * | 1961-12-18 | |||
| US3249585A (en) * | 1964-04-29 | 1966-05-03 | Dow Corning | Preparation of siloxanes with sih bonds with an alkyl lithium catalyst |
| US3394160A (en) * | 1964-12-28 | 1968-07-23 | Gen Electric | Cyclopolysiloxanes |
| US3337497A (en) * | 1966-04-11 | 1967-08-22 | Gen Electric | Ordered organopolysiloxanes |
| US3503926A (en) * | 1968-05-17 | 1970-03-31 | Dow Corning | Solid lubricant composition |
| JPS5249038B1 (Direct) * | 1970-08-25 | 1977-12-14 |
-
1975
- 1975-10-09 US US05/621,032 patent/US4028338A/en not_active Expired - Lifetime
-
1976
- 1976-10-07 DE DE19762645298 patent/DE2645298A1/de not_active Withdrawn
- 1976-10-07 GB GB41677/76A patent/GB1558816A/en not_active Expired
- 1976-10-07 FR FR7630161A patent/FR2327272A1/fr active Granted
- 1976-10-08 JP JP51120455A patent/JPS6033846B2/ja not_active Expired
- 1976-12-15 US US05/750,994 patent/US4075169A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1558816A (en) | 1980-01-09 |
| FR2327272A1 (fr) | 1977-05-06 |
| US4028338A (en) | 1977-06-07 |
| US4075169A (en) | 1978-02-21 |
| FR2327272B1 (Direct) | 1980-05-30 |
| DE2645298A1 (de) | 1977-04-14 |
| JPS5256200A (en) | 1977-05-09 |
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