CA1304092C - Imidopolysiloxanes et methode pour leur fabrication - Google Patents
Imidopolysiloxanes et methode pour leur fabricationInfo
- Publication number
- CA1304092C CA1304092C CA000545571A CA545571A CA1304092C CA 1304092 C CA1304092 C CA 1304092C CA 000545571 A CA000545571 A CA 000545571A CA 545571 A CA545571 A CA 545571A CA 1304092 C CA1304092 C CA 1304092C
- Authority
- CA
- Canada
- Prior art keywords
- imidopolysiloxane
- inclusive
- radicals
- hydrocarbon radicals
- formula
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title abstract description 7
- 239000011347 resin Substances 0.000 claims abstract description 8
- 229920005989 resin Polymers 0.000 claims abstract description 8
- 239000012530 fluid Substances 0.000 claims abstract description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 150000003949 imides Chemical class 0.000 claims description 7
- 229920001296 polysiloxane Polymers 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 5
- 125000003106 haloaryl group Chemical group 0.000 claims description 4
- 125000004999 nitroaryl group Chemical group 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 239000000945 filler Substances 0.000 claims 1
- 150000002978 peroxides Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 9
- 150000001282 organosilanes Chemical class 0.000 abstract description 4
- 229920001971 elastomer Polymers 0.000 abstract description 2
- 239000000806 elastomer Substances 0.000 abstract description 2
- -1 silyl imides Chemical class 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RZJCVRGXBXQONK-UHFFFAOYSA-N C1=C([SiH2]C(Cl)Cl)C=C2C(=O)N(C)C(=O)C2=C1 Chemical compound C1=C([SiH2]C(Cl)Cl)C=C2C(=O)N(C)C(=O)C2=C1 RZJCVRGXBXQONK-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229920000557 Nafion® Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012763 reinforcing filler Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 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
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- BXHLWHLRFBMRTC-UHFFFAOYSA-N 4-butyl-5-chloroisoindole-1,3-dione Chemical compound C1=C(Cl)C(CCCC)=C2C(=O)NC(=O)C2=C1 BXHLWHLRFBMRTC-UHFFFAOYSA-N 0.000 description 1
- DCFSQEWFDPNDPQ-UHFFFAOYSA-N 5-chloro-2-methylisoindole-1,3-dione Chemical compound C1=C(Cl)C=C2C(=O)N(C)C(=O)C2=C1 DCFSQEWFDPNDPQ-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 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
- QISCFNMOKLZAOA-UHFFFAOYSA-N C(C)N1C(C=2C(C1=O)=C(C(=CC2)Cl)[SiH](C)C)=O Chemical compound C(C)N1C(C=2C(C1=O)=C(C(=CC2)Cl)[SiH](C)C)=O QISCFNMOKLZAOA-UHFFFAOYSA-N 0.000 description 1
- VYUSCKGWKHZQRI-UHFFFAOYSA-N C1(=CC=CC=C1)N1C(C=2C(C1=O)=CC(=CC2)[SiH2]C(Cl)Cl)=O Chemical compound C1(=CC=CC=C1)N1C(C=2C(C1=O)=CC(=CC2)[SiH2]C(Cl)Cl)=O VYUSCKGWKHZQRI-UHFFFAOYSA-N 0.000 description 1
- YFSDADMEAHIVAG-UHFFFAOYSA-N CN1C(C=2C(C1=O)=C(C(=CC2)Cl)[SiH](C)C)=O Chemical compound CN1C(C=2C(C1=O)=C(C(=CC2)Cl)[SiH](C)C)=O YFSDADMEAHIVAG-UHFFFAOYSA-N 0.000 description 1
- LEHLWSHAWXUKBO-UHFFFAOYSA-N CN1C(C=2C(C1=O)=C(C(=CC2)OC)[SiH](C)C)=O Chemical compound CN1C(C=2C(C1=O)=C(C(=CC2)OC)[SiH](C)C)=O LEHLWSHAWXUKBO-UHFFFAOYSA-N 0.000 description 1
- XKMDUTBVUSAOOY-UHFFFAOYSA-N CN1C(C=2C(C1=O)=CC(=CC2)[SiH](OC)OC)=O Chemical compound CN1C(C=2C(C1=O)=CC(=CC2)[SiH](OC)OC)=O XKMDUTBVUSAOOY-UHFFFAOYSA-N 0.000 description 1
- UYXLOULABOHUAJ-UHFFFAOYSA-N CO[SiH](OC)CCC1=CC=CC=C1 Chemical compound CO[SiH](OC)CCC1=CC=CC=C1 UYXLOULABOHUAJ-UHFFFAOYSA-N 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- HMDDXIMCDZRSNE-UHFFFAOYSA-N [C].[Si] Chemical compound [C].[Si] HMDDXIMCDZRSNE-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 229960003328 benzoyl peroxide Drugs 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- BQLQQEHXQQLKEV-UHFFFAOYSA-N dimethoxy-methyl-trimethylsilylsilane Chemical compound CO[Si](C)(OC)[Si](C)(C)C BQLQQEHXQQLKEV-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 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
- JESHZQPNPCJVNG-UHFFFAOYSA-L magnesium;sulfite Chemical compound [Mg+2].[O-]S([O-])=O JESHZQPNPCJVNG-UHFFFAOYSA-L 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229940078552 o-xylene Drugs 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- CIHXQOLAODJUPA-UHFFFAOYSA-N prop-1-enyl(silyloxysilyloxysilyloxy)silane Chemical compound CC=C[SiH2]O[SiH2]O[SiH2]O[SiH3] CIHXQOLAODJUPA-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
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-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
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
-
- 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
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
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)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US90281486A | 1986-09-02 | 1986-09-02 | |
US902,814 | 1986-09-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1304092C true CA1304092C (fr) | 1992-06-23 |
Family
ID=25416435
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA000545571A Expired - Fee Related CA1304092C (fr) | 1986-09-02 | 1987-08-27 | Imidopolysiloxanes et methode pour leur fabrication |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPH066627B2 (fr) |
CA (1) | CA1304092C (fr) |
DE (1) | DE3715313A1 (fr) |
FR (1) | FR2603289B1 (fr) |
GB (1) | GB2194544B (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4730055A (en) * | 1984-09-04 | 1988-03-08 | General Electric Company | Method for silylating aromatic imides and silylimides made therefrom |
CN101910318B (zh) * | 2008-01-28 | 2012-10-24 | 东丽株式会社 | 硅氧烷类树脂组合物 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH634851A5 (de) * | 1977-09-09 | 1983-02-28 | Ciba Geigy Ag | Verfahren zur herstellung von imidyl- und silylgruppenhaltigen polymeren. |
US4522985A (en) * | 1984-04-27 | 1985-06-11 | General Electric Company | Heat curable silicone-polyimide block copolymers |
US4595732A (en) * | 1984-04-27 | 1986-06-17 | General Electric Company | Siloxane imide diols and siloxane imide organic block polymers obtained therefrom |
GB2164040B (en) * | 1984-09-04 | 1988-10-05 | Gen Electric | Method for silylating aromatic imides and imides made therefrom |
DE3542346C2 (de) * | 1984-12-05 | 1997-06-12 | Gen Electric | Anhydrid-Siloxane und Polyanhydrid-Siloxane |
GB2168065B (en) * | 1984-12-05 | 1990-04-25 | Gen Electric | Polyanhydride-siloxanes and polyimide-siloxanes obtained therefrom |
-
1987
- 1987-05-08 DE DE19873715313 patent/DE3715313A1/de not_active Ceased
- 1987-06-03 GB GB8713014A patent/GB2194544B/en not_active Expired - Fee Related
- 1987-08-27 CA CA000545571A patent/CA1304092C/fr not_active Expired - Fee Related
- 1987-09-01 FR FR878712144A patent/FR2603289B1/fr not_active Expired - Fee Related
- 1987-09-02 JP JP62218105A patent/JPH066627B2/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
GB2194544B (en) | 1991-06-19 |
DE3715313A1 (de) | 1988-03-10 |
GB2194544A (en) | 1988-03-09 |
GB8713014D0 (en) | 1987-07-08 |
JPH066627B2 (ja) | 1994-01-26 |
FR2603289B1 (fr) | 1991-05-24 |
JPS63108028A (ja) | 1988-05-12 |
FR2603289A1 (fr) | 1988-03-04 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MKLA | Lapsed |