CA1051587A - Low temperature reversion resistant organosilicon polymers - Google Patents
Low temperature reversion resistant organosilicon polymersInfo
- Publication number
- CA1051587A CA1051587A CA246,810A CA246810A CA1051587A CA 1051587 A CA1051587 A CA 1051587A CA 246810 A CA246810 A CA 246810A CA 1051587 A CA1051587 A CA 1051587A
- Authority
- CA
- Canada
- Prior art keywords
- polymers
- low temperature
- moles
- type
- 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.)
- Expired
Links
- 229920001558 organosilicon polymer Polymers 0.000 title description 2
- 230000009973 reversion resistant effect Effects 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 239000004971 Cross linker Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 2
- 229920001971 elastomer Polymers 0.000 abstract description 4
- 239000002828 fuel tank Substances 0.000 abstract description 2
- 238000007789 sealing Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000005060 rubber Substances 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- -1 siloxane units Chemical group 0.000 description 14
- 150000002009 diols Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- HUWNGKVNXAXAMN-UHFFFAOYSA-N methyl(3,3,3-trifluoropropyl)silane Chemical compound C[SiH2]CCC(F)(F)F HUWNGKVNXAXAMN-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 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 2
- 239000000806 elastomer Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NWTFAHUFNCOOMA-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CN(C)C(=N)N(C)C NWTFAHUFNCOOMA-UHFFFAOYSA-N 0.000 description 1
- JQZGUQIEPRIDMR-UHFFFAOYSA-N 3-methylbut-1-yn-1-ol Chemical compound CC(C)C#CO JQZGUQIEPRIDMR-UHFFFAOYSA-N 0.000 description 1
- 241000566146 Asio Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 101150029512 SCG2 gene Proteins 0.000 description 1
- 229910020175 SiOH Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- XTDIMSIXPZOLRN-UHFFFAOYSA-N methyl-silyloxy-(3,3,3-trifluoropropyl)silane Chemical compound [SiH3]O[SiH](C)CCC(F)(F)F XTDIMSIXPZOLRN-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides 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
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
-
- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/485—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms containing less than 25 silicon atoms
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)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/572,583 US3975362A (en) | 1975-04-28 | 1975-04-28 | Low temperature reversion resistant organosilicon polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1051587A true CA1051587A (en) | 1979-03-27 |
Family
ID=24288482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA246,810A Expired CA1051587A (en) | 1975-04-28 | 1976-03-01 | Low temperature reversion resistant organosilicon polymers |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3975362A (enExample) |
| JP (1) | JPS51131600A (enExample) |
| CA (1) | CA1051587A (enExample) |
| DE (1) | DE2618418C3 (enExample) |
| FR (1) | FR2309572A1 (enExample) |
| GB (1) | GB1538617A (enExample) |
| SE (1) | SE414776B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4057566A (en) * | 1976-01-08 | 1977-11-08 | Dow Corning Corporation | Fluorocarbon siloxane compositions |
| US4488771A (en) * | 1982-03-08 | 1984-12-18 | Allied Corporation | Fluorosilicone elastomers, method of making such elastomers and electrical connectors including the elastomers |
| US4492786A (en) * | 1983-08-26 | 1985-01-08 | General Electric Company | Modified organopolysiloxane composition |
| US4565714B1 (en) * | 1984-06-14 | 1999-06-29 | Minnesota Mining & Mfg | Low surface energy material |
| JPS63235367A (ja) * | 1987-03-24 | 1988-09-30 | Shin Etsu Chem Co Ltd | オルガノポリシロキサン組成物 |
| DE69119980T2 (de) * | 1990-07-06 | 1997-02-13 | Shinetsu Chemical Co | Polysilethylensiloxan |
| JPH0692482B2 (ja) * | 1991-06-27 | 1994-11-16 | 信越化学工業株式会社 | 有機けい素化合物 |
| US20050038188A1 (en) * | 2003-08-14 | 2005-02-17 | Dongchan Ahn | Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance |
| US7045586B2 (en) * | 2003-08-14 | 2006-05-16 | Dow Corning Corporation | Adhesives having improved chemical resistance and curable silicone compositions for preparing the adhesives |
| US20050038183A1 (en) * | 2003-08-14 | 2005-02-17 | Dongchan Ahn | Silicones having improved surface properties and curable silicone compositions for preparing the silicones |
| US8153200B2 (en) * | 2005-10-17 | 2012-04-10 | MIRteq Pty Ltd. | Method for treating reinforcing fibre and method for producing a reinforced composite article from the treated fibre |
| US11753507B2 (en) * | 2020-12-23 | 2023-09-12 | Momentive Performance Materials Inc. | Addition curable composition comprising siloxane-imide copolymers |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3542830A (en) * | 1968-08-02 | 1970-11-24 | Dow Corning | Fluorocarbon silicone compositions |
-
1975
- 1975-04-28 US US05/572,583 patent/US3975362A/en not_active Expired - Lifetime
-
1976
- 1976-03-01 CA CA246,810A patent/CA1051587A/en not_active Expired
- 1976-03-25 SE SE7603624A patent/SE414776B/xx not_active IP Right Cessation
- 1976-03-30 GB GB12703/76A patent/GB1538617A/en not_active Expired
- 1976-04-26 JP JP51047585A patent/JPS51131600A/ja active Granted
- 1976-04-27 DE DE2618418A patent/DE2618418C3/de not_active Expired
- 1976-04-27 FR FR7612404A patent/FR2309572A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2309572A1 (fr) | 1976-11-26 |
| SE7603624L (sv) | 1976-10-29 |
| DE2618418C3 (de) | 1978-07-13 |
| SE414776B (sv) | 1980-08-18 |
| JPS51131600A (en) | 1976-11-16 |
| JPS543797B2 (enExample) | 1979-02-27 |
| FR2309572B1 (enExample) | 1979-09-07 |
| DE2618418A1 (de) | 1976-11-04 |
| DE2618418B2 (de) | 1977-11-24 |
| GB1538617A (en) | 1979-01-24 |
| US3975362A (en) | 1976-08-17 |
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