GB1014051A - Novel silanes and siloxanes - Google Patents
Novel silanes and siloxanesInfo
- Publication number
- GB1014051A GB1014051A GB2906861A GB2906861A GB1014051A GB 1014051 A GB1014051 A GB 1014051A GB 2906861 A GB2906861 A GB 2906861A GB 2906861 A GB2906861 A GB 2906861A GB 1014051 A GB1014051 A GB 1014051A
- Authority
- GB
- United Kingdom
- Prior art keywords
- monovalent hydrocarbon
- silanes
- product
- group
- general 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
Links
- -1 siloxanes Chemical class 0.000 title abstract 14
- 150000004756 silanes Chemical class 0.000 title abstract 7
- 239000004215 Carbon black (E152) Substances 0.000 abstract 9
- 229930195733 hydrocarbon Natural products 0.000 abstract 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 238000007334 copolymerization reaction Methods 0.000 abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 abstract 3
- 229910000077 silane Inorganic materials 0.000 abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- GBZANISLBWFGTD-UHFFFAOYSA-N bis(2-chlorosilyl-2-methylpropyl)-phenylphosphane Chemical compound C1(=CC=CC=C1)P(CC(C)(C)[SiH2]Cl)CC([SiH2]Cl)(C)C GBZANISLBWFGTD-UHFFFAOYSA-N 0.000 abstract 2
- XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 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
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 239000005047 Allyltrichlorosilane Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 abstract 1
- 239000002981 blocking agent Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000004132 cross linking Methods 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004205 dimethyl polysiloxane Substances 0.000 abstract 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 abstract 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 abstract 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000001282 organosilanes Chemical class 0.000 abstract 1
- 150000003961 organosilicon compounds Chemical class 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004437 phosphorous atom Chemical group 0.000 abstract 1
- 150000003018 phosphorus compounds Chemical class 0.000 abstract 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 150000004760 silicates Chemical class 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- 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
-
- 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
- C07F7/12—Organo silicon halides
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
Abstract
The invention comprises (a) silanes of general formula <FORM:1014051/C3/1> wherein R1 and R11 are monovalent hydrocarbon or halogenated monovalent hydrocarbon radicals, Q is a phosphorus atom or the groups P=O or P=S; Z is a divalent hydrocarbon radical of at least two carbon atoms and is free of aliphatic unsaturation; Y is a halogen, alkoxy or acyloxy group; X is 0 or 1 and b is 0, 1 or 2; and (b) their corresponding polysiloxanes and copolymers thereof with other silanes and siloxanes. The silanes are prepared by reacting a compound R1PH2; <FORM:1014051/C3/2> wherein R1 is hydrogen, a monovalent hydrocarbon radical or halogenated monovalent hydrocarbon radical with a silane containing an olefinically unsaturated substituent and at least one hydrolysable group, e.g. halogen, alkoxy or acyloxy, the remaining valencies of the silicon atom being satisfied with monovalent hydrocarbon or halogenated monovalent hydrocarbon radicals. The silanes used have the general formula Y3- bR11bSiB wherein Y and R11 are as defined above; B is a vinyl or allyl radical and b is 0, 1 or 2. The reaction preferably takes place in the presence of a free radical source as catalyst, e.g. azobisisobutyronitrile or ultra-violet light. R1 and R11 may be methyl, ethyl, propyl, phenyl and chlorophenyl radicals. Organosilanes used are vinyl dimethylchlorosilane, vinyl methyl dichlorosilane and allyltrichlorosilane. In addition the trivalent phosphorus containing silanes may be oxidized to the corresponding pentavalent phosphorus compounds containing the groups P=O or P=S by reaction with an oxidizing agent, e.g. a peroxide or sulphur. Siloxane polymers of the unit general formula <FORM:1014051/C3/3> wherein R1, R11, Q, Z, b and X are as defined above and are prepared by hydrolysis of the corresponding tervalent or pentavalent silanes, preferably by adding a solution of the silane in benzene or toluene to water with cooling at 0-15 DEG C. The linear siloxanes may have hydroxy or alkoxy groups directly attached to the terminal silicon atoms, thus enabling further polymerization or cross-linking with silicates and polysilicates to occur. Copolymers are obtained by reaction with linear or cyclic siloxanes of general formula <FORM:1014051/C3/4> wherein A is a monovalent hydrocarbon radical or substituted monovalent hydrocarbon radical and m has an average value of 1-3, e.g. linear or cyclic dimethylpolysiloxane; or alternatively by cohydrolysis of a phosphorus containing silane with an organosilicon compound, e.g. dimethyl dichlorosilane. Copolymerization may also take place with blocking agents containing the trimethylsiloxy group. The examples describe (1) reaction of phenylphosphine and dimethylvinylchlorosilane in presence of azobisisobutyronitrile to give phenyl bis-(dimethylchlorosilylethyl)phosphine; (2) hydrolysis of the product in (1) to give <FORM:1014051/C3/5> ; (3) oxidation of the product of Example (2) to introduce the P=O group; (4) oxidation of the product of Example (2) to introduce the P=S group; (5) co-polymerization of the product of Example (3) with octamethyl cyclotetrasiloxane and hexamethyldisiloxane, and (6) the copolymerization of the product of Example (2) with octamethylcyclotetrasiloxane and hexamethyldisiloxane in presence of sulphur.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2906861A GB1014051A (en) | 1961-08-11 | 1961-08-11 | Novel silanes and siloxanes |
| DEM53843A DE1175672B (en) | 1961-08-11 | 1962-08-09 | Process for the production of phosphorus-containing siloxanes |
| FR906735A FR1340233A (en) | 1961-08-11 | 1962-08-10 | New silanes containing phosphorus, their derivatives and their preparation process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2906861A GB1014051A (en) | 1961-08-11 | 1961-08-11 | Novel silanes and siloxanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1014051A true GB1014051A (en) | 1965-12-22 |
Family
ID=10285673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2906861A Expired GB1014051A (en) | 1961-08-11 | 1961-08-11 | Novel silanes and siloxanes |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1175672B (en) |
| GB (1) | GB1014051A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2912430A1 (en) * | 1978-03-30 | 1979-10-04 | Dow Corning | ALKALINE SILICONATE SILYLALKYLPHOSPHONATE |
-
1961
- 1961-08-11 GB GB2906861A patent/GB1014051A/en not_active Expired
-
1962
- 1962-08-09 DE DEM53843A patent/DE1175672B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2912430A1 (en) * | 1978-03-30 | 1979-10-04 | Dow Corning | ALKALINE SILICONATE SILYLALKYLPHOSPHONATE |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1175672B (en) | 1964-08-13 |
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