GB980109A - Trifluoromethylphenyl polysiloxanes - Google Patents
Trifluoromethylphenyl polysiloxanesInfo
- Publication number
- GB980109A GB980109A GB47648/62A GB4764862A GB980109A GB 980109 A GB980109 A GB 980109A GB 47648/62 A GB47648/62 A GB 47648/62A GB 4764862 A GB4764862 A GB 4764862A GB 980109 A GB980109 A GB 980109A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polymers
- preparation
- compounds
- polysiloxanes
- octamethylcyclotetrasiloxane
- 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
- -1 Trifluoromethylphenyl Chemical group 0.000 title abstract 4
- 229920001296 polysiloxane Polymers 0.000 title abstract 3
- 229920000642 polymer Polymers 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- ZUFQVQACAFNOML-UHFFFAOYSA-N 2,2,4,6-tetraphenyl-4-(2-phenylphenyl)-6-(trifluoromethyl)-1,3,5,2,4,6-trioxatrisilinane Chemical compound FC([Si]1(O[Si](O[Si](O1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=C(C=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)(F)F ZUFQVQACAFNOML-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000004964 aerogel Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000010425 asbestos Substances 0.000 abstract 1
- 230000005540 biological transmission Effects 0.000 abstract 1
- CMWRUTZCSFMXJQ-UHFFFAOYSA-N bis(triphenylsilyloxy)silicon Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si]O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CMWRUTZCSFMXJQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 235000010216 calcium carbonate Nutrition 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000006229 carbon black Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 abstract 1
- 238000005538 encapsulation Methods 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 239000003365 glass fiber Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- UJVRJBAUJYZFIX-UHFFFAOYSA-N nitric acid;oxozirconium Chemical compound [Zr]=O.O[N+]([O-])=O.O[N+]([O-])=O UJVRJBAUJYZFIX-UHFFFAOYSA-N 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 230000000306 recurrent effect Effects 0.000 abstract 1
- 229910052895 riebeckite Inorganic materials 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- PTUUTGJMRQWABQ-UHFFFAOYSA-N triphenyl(phenylsilyloxy)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[SiH2]C1=CC=CC=C1 PTUUTGJMRQWABQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 229910052882 wollastonite Inorganic materials 0.000 abstract 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
-
- 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
-
- 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
- C08G77/48—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
- C08G77/52—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 containing aromatic rings
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)
Abstract
The invention comprises compounds of the formula <FORM:0980109/C3/1> where n and a are each 0 or 1, and b is 1, 2, or 3, and R is a monovalent hydrocarbon radical without aliphatic unsaturation, and polymers thereof. They are prepared by the reaction of tetraphenyl disiloxane diol-1,3 or hexaphenyl trisiloxane diol-1,5 with the appropriate organohalosilane <FORM:0980109/C3/2> where X is halogen, and a is as above, in an inert solvent, in the presence of a hydrogen halide acceptor, e.g. a tertiary amine, in particular pyridine. Polymers containing the recurrent unit <FORM:0980109/C3/3> where a, b and n, and R are as above, are prepared by heating the compounds (I) alone at 250-350 DEG C., or, preferably, with a catalyst at 120-170 DEG C. A suitable catalyst is a 0.01-1% solution of KOH in octamethylcyclotetrasiloxane, amounting to 10-100 p.p.m. of KOH in the monomer. Copolymers of compounds (I) with themselves or other cyclic polysiloxanes, e.g. those of Specifications 980,101, 980,102, 980,103, 980,104, 980,105, 980,106, 980,107 and 980,108, or cyclic dialkyl- or diaryl-polysiloxanes, are made from mixtures in the same way. All polymers containing units (II) can be cross-linked by irradiation, e.g. with 50,000-20,000,000 eV electrons, and those containing vinyl, cyclo alkyl or adjacent methyl groups, or alkyl groups with more than one carbon atom, can be cured with conventional free radical (e.g. peroxide or zirconyl nitrate) curing agents. Fillers may be added before cure, if desired, and may suitably be silica (aerogel, fumed, precipitated), TiO2, CaCO3, CaSiO3, Fe2O3, Cr2O3, CdS, lithopone, asbestos, talc, carbon black, glass fibres &c. The examples describe the preparation of 1,1 - bis - (m - trifluromethylphenyl)tetraphenyl cyclotrisiloxane and of p-trifluoromethylphenyl pentaphenyl cyclotrisiloxane, and the preparation and use of their polymers for encapsulation of transformers. Also described is the preparation, and cure by irradiation, of a copolymer of octamethylcyclotetrasiloxane with 1-methyl-1 - [3,5 - bis - (trifluoromethyl) - phenyl] - hexaphenylcyclotetrasiloxane. Uses:-Seals in automotive transmissions, flexible supports for elements to be used in atomic reactors.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US160272A US3328348A (en) | 1961-12-18 | 1961-12-18 | Trifluoromethylphenyl polysiloxanes |
| US160262A US3318935A (en) | 1961-12-18 | 1961-12-18 | Organosilicon material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB980109A true GB980109A (en) | 1965-01-13 |
Family
ID=26856740
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47648/62A Expired GB980109A (en) | 1961-12-18 | 1962-12-18 | Trifluoromethylphenyl polysiloxanes |
| GB47641/62A Expired GB980102A (en) | 1961-12-18 | 1962-12-18 | Phenyl polysiloxanes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47641/62A Expired GB980102A (en) | 1961-12-18 | 1962-12-18 | Phenyl polysiloxanes |
Country Status (2)
| Country | Link |
|---|---|
| DE (2) | DE1495890A1 (en) |
| GB (2) | GB980109A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015016730A2 (en) | 2013-08-02 | 2015-02-05 | Active Aerogels, Unipessoal, Lda. | Method for production of flexible panels of hydrophobic aerogel reinforced with fibre felts |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2655050B1 (en) * | 1989-11-24 | 1992-03-20 | Rhone Poulenc Chimie | THERMOTROPIC MACROCYCLES CONSISTING OF MESOGENIC BLOCKS OF THE AROMATIC AZOMETHINE TYPE AND DIORGANOPOLYSILOXANE BLOCKS AND THEIR PREPARATION METHOD. |
-
1962
- 1962-12-18 DE DE19621495890 patent/DE1495890A1/en active Pending
- 1962-12-18 GB GB47648/62A patent/GB980109A/en not_active Expired
- 1962-12-18 GB GB47641/62A patent/GB980102A/en not_active Expired
- 1962-12-18 DE DE19621495894 patent/DE1495894A1/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015016730A2 (en) | 2013-08-02 | 2015-02-05 | Active Aerogels, Unipessoal, Lda. | Method for production of flexible panels of hydrophobic aerogel reinforced with fibre felts |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1495894A1 (en) | 1969-10-09 |
| GB980102A (en) | 1965-01-13 |
| DE1495890A1 (en) | 1969-05-14 |
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