DE2945786A1 - Verfahren zum herstellen von fluorsilikon-polymeren - Google Patents
Verfahren zum herstellen von fluorsilikon-polymerenInfo
- Publication number
- DE2945786A1 DE2945786A1 DE19792945786 DE2945786A DE2945786A1 DE 2945786 A1 DE2945786 A1 DE 2945786A1 DE 19792945786 DE19792945786 DE 19792945786 DE 2945786 A DE2945786 A DE 2945786A DE 2945786 A1 DE2945786 A1 DE 2945786A1
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- formula
- polymerization catalyst
- radical
- polymer
- 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- Withdrawn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
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 229920005573 silicon-containing polymer Polymers 0.000 title description 2
- -1 hydrocarbon radicals Chemical class 0.000 claims description 75
- 229920000642 polymer Polymers 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 58
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 claims description 40
- 239000002685 polymerization catalyst Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000000945 filler Substances 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 229920001971 elastomer Polymers 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 229920002379 silicone rubber Polymers 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000000470 constituent Substances 0.000 claims description 9
- 229920001296 polysiloxane Polymers 0.000 claims description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000003472 neutralizing effect Effects 0.000 claims description 8
- YIKQLNRXIWIZFA-UHFFFAOYSA-N silyl dihydrogen phosphate Chemical compound OP(O)(=O)O[SiH3] YIKQLNRXIWIZFA-UHFFFAOYSA-N 0.000 claims description 8
- 125000000962 organic group Chemical group 0.000 claims description 7
- 239000004945 silicone rubber Substances 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- MDLWEBWGXACWGE-UHFFFAOYSA-N octadecane Chemical group [CH2]CCCCCCCCCCCCCCCCC MDLWEBWGXACWGE-UHFFFAOYSA-N 0.000 claims description 2
- 239000003039 volatile agent Substances 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- 210000001747 pupil Anatomy 0.000 claims 1
- 150000004756 silanes Chemical class 0.000 claims 1
- 150000003527 tetrahydropyrans Chemical class 0.000 claims 1
- JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- DDJSWKLBKSLAAZ-UHFFFAOYSA-N cyclotetrasiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]O[SiH2]1 DDJSWKLBKSLAAZ-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 14
- 125000005372 silanol group Chemical group 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229920005601 base polymer Polymers 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 239000006057 Non-nutritive feed additive Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000005336 cracking Methods 0.000 description 5
- 238000011067 equilibration Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000005840 aryl radicals Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920002959 polymer blend Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- USMAJEUNEOOWAE-UHFFFAOYSA-N 2-(3-fluoropropyl)-2-methyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound C[Si]1(O[SiH2]O[SiH2]O1)CCCF USMAJEUNEOOWAE-UHFFFAOYSA-N 0.000 description 2
- MOAZYHBAIJHHKZ-UHFFFAOYSA-N 2-ethenyl-2-methyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound C[Si]1(O[SiH2]O[SiH2]O1)C=C MOAZYHBAIJHHKZ-UHFFFAOYSA-N 0.000 description 2
- FGZFESWHQXSPJU-UHFFFAOYSA-N 2-methyl-2-(3,3,3-trifluoropropyl)-1,3,5,2,4,6-trioxatrisilinane Chemical compound FC(F)(F)CC[Si]1(C)O[SiH2]O[SiH2]O1 FGZFESWHQXSPJU-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 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 2
- 239000000806 elastomer Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- JVQPFLDUNXEOTF-UHFFFAOYSA-N sodium fluoro(oxido)silane Chemical compound [Na+].[O-][SiH2]F JVQPFLDUNXEOTF-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-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
- JGWUKKFNKOUBPW-UHFFFAOYSA-N 2-ethenyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[SiH]1O[SiH2]O[SiH2]O[SiH2]O1 JGWUKKFNKOUBPW-UHFFFAOYSA-N 0.000 description 1
- ZLODZDLDZBRDLS-UHFFFAOYSA-N 2-prop-1-enyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical class CC=C[SiH]1O[SiH2]O[SiH2]O[SiH2]O1 ZLODZDLDZBRDLS-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- FLMFGWYBTAFPAQ-UHFFFAOYSA-N bis[[hydroxy-methyl-(3,3,3-trifluoropropyl)silyl]oxy]-methyl-(3,3,3-trifluoropropyl)silane Chemical compound FC(F)(F)CC[Si](O)(C)O[Si](C)(CCC(F)(F)F)O[Si](C)(O)CCC(F)(F)F FLMFGWYBTAFPAQ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- LWIGVRDDANOFTD-UHFFFAOYSA-N hydroxy(dimethyl)silane Chemical compound C[SiH](C)O LWIGVRDDANOFTD-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229920006120 non-fluorinated polymer Polymers 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- IALUUOKJPBOFJL-UHFFFAOYSA-N potassium oxidosilane Chemical compound [K+].[SiH3][O-] IALUUOKJPBOFJL-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004448 titration 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
- C08G77/22—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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95954478A | 1978-11-13 | 1978-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2945786A1 true DE2945786A1 (de) | 1980-05-22 |
Family
ID=25502123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792945786 Withdrawn DE2945786A1 (de) | 1978-11-13 | 1979-11-13 | Verfahren zum herstellen von fluorsilikon-polymeren |
Country Status (4)
| Country | Link |
|---|---|
| JP (2) | JPS5580434A (enExample) |
| DE (1) | DE2945786A1 (enExample) |
| FR (2) | FR2441640A1 (enExample) |
| GB (4) | GB2036770B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4355121A (en) * | 1981-04-09 | 1982-10-19 | General Electric Company | Heat strength curable silicone rubber compositions |
| US4492786A (en) * | 1983-08-26 | 1985-01-08 | General Electric Company | Modified organopolysiloxane composition |
| US4897459A (en) * | 1987-11-25 | 1990-01-30 | General Electric Company | Catalyst for producing fluorosilicone polymers |
| US4882368A (en) * | 1988-09-26 | 1989-11-21 | Dow Corning Corporation | Low compression set fluorosilicone rubber |
| JPH0643555B2 (ja) * | 1989-07-06 | 1994-06-08 | 信越化学工業株式会社 | フルオロシリコーンゴム組成物の製造方法 |
| US5081172A (en) * | 1989-12-13 | 1992-01-14 | Dow Corning Corporation | Method to reduce compression set in silanol-containing silicone elastomer bases |
| GB2345292B (en) * | 1998-12-31 | 2004-06-23 | Gen Electric | Process for producing fluorosilicone polymers |
| US6451954B1 (en) * | 2000-07-27 | 2002-09-17 | General Electric Company | Copolymer sealant compositions and method for making |
| USD475281S1 (en) | 2002-01-31 | 2003-06-03 | Colgate-Palmolive Company | Dispenser |
| 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 |
| USD793867S1 (en) | 2015-08-28 | 2017-08-08 | The Procter & Gamble Company | Container |
| USD794465S1 (en) | 2015-08-28 | 2017-08-15 | The Procter & Gamble Company | Container |
| USD793250S1 (en) | 2015-09-07 | 2017-08-01 | The Procter & Gamble Company | Container |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3002951A (en) * | 1959-04-27 | 1961-10-03 | Dow Corning | Method of polymerizing cyclic diorganosiloxanes |
| FR1279876A (fr) * | 1961-02-14 | 1961-12-22 | Dow Corning | Procédé de polymérisation des cyclotrisiloxanes substitués par des groupements fluoroalkyles |
| US3146251A (en) * | 1961-07-31 | 1964-08-25 | Dow Corning | Preparation of linear siloxanes |
| US3779987A (en) * | 1972-10-12 | 1973-12-18 | Gen Electric | Process for producing diorganopolysiloxane polymers |
| DE2618815A1 (de) * | 1975-05-05 | 1976-11-18 | Gen Electric | Verfahren zum polymerisieren cyclischer diorganopolysiloxane |
-
1979
- 1979-11-02 JP JP14145579A patent/JPS5580434A/ja active Granted
- 1979-11-06 GB GB7938392A patent/GB2036770B/en not_active Expired
- 1979-11-13 DE DE19792945786 patent/DE2945786A1/de not_active Withdrawn
- 1979-11-13 FR FR7927917A patent/FR2441640A1/fr active Granted
-
1980
- 1980-03-27 FR FR8006794A patent/FR2443477A1/fr active Granted
-
1983
- 1983-01-28 GB GB08302363A patent/GB2118960B/en not_active Expired
- 1983-01-28 GB GB08302362A patent/GB2118959B/en not_active Expired
- 1983-01-28 GB GB838302364A patent/GB8302364D0/en active Pending
-
1987
- 1987-10-14 JP JP25750087A patent/JPH0244852B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB2036770A (en) | 1980-07-02 |
| GB2118960B (en) | 1984-04-11 |
| GB2118959B (en) | 1984-04-11 |
| FR2441640A1 (fr) | 1980-06-13 |
| FR2441640B1 (enExample) | 1985-04-05 |
| JPS63125527A (ja) | 1988-05-28 |
| GB2118959A (en) | 1983-11-09 |
| FR2443477B1 (enExample) | 1983-12-23 |
| GB8302363D0 (en) | 1983-03-02 |
| GB2036770B (en) | 1983-11-02 |
| JPS5580434A (en) | 1980-06-17 |
| GB8302364D0 (en) | 1983-03-02 |
| JPS6317093B2 (enExample) | 1988-04-12 |
| GB2118960A (en) | 1983-11-09 |
| JPH0244852B2 (ja) | 1990-10-05 |
| FR2443477A1 (fr) | 1980-07-04 |
| GB8302362D0 (en) | 1983-03-02 |
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