GB758168A - Organosilicon compounds - Google Patents
Organosilicon compoundsInfo
- Publication number
- GB758168A GB758168A GB25834/54A GB2583454A GB758168A GB 758168 A GB758168 A GB 758168A GB 25834/54 A GB25834/54 A GB 25834/54A GB 2583454 A GB2583454 A GB 2583454A GB 758168 A GB758168 A GB 758168A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- prepared
- methyl
- compounds
- disiloxane
- 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
- 150000003961 organosilicon compounds Chemical class 0.000 title 1
- -1 polysiloxanes Polymers 0.000 abstract 14
- 150000001875 compounds Chemical class 0.000 abstract 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 6
- 239000004215 Carbon black (E152) Substances 0.000 abstract 4
- 229930195733 hydrocarbon Natural products 0.000 abstract 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 229920001296 polysiloxane Polymers 0.000 abstract 3
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 125000004188 dichlorophenyl group Chemical group 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 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
- AMJQJHHAPXSEIZ-UHFFFAOYSA-N trimethyl-[[methylsilyloxy(diphenyl)silyl]oxy-diphenylsilyl]oxysilane Chemical compound C[SiH2]O[Si](O[Si](O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 AMJQJHHAPXSEIZ-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- OPQZBLJYYYEWJO-UHFFFAOYSA-N dimethyl-(1-phenyl-5-piperidin-1-ylpentyl)silane Chemical compound C1(=CC=CC=C1)C(CCCCN1CCCCC1)[SiH](C)C OPQZBLJYYYEWJO-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
- 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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Abstract
The invention comprises polysiloxanes, which are end-blocked by piperidine radicals, of the formula <FORM:0758168/IV(a)/1> where R1 is a monovalent hydrocarbon or halogenated aryl hydrocarbon radical, n is from 2 to 5 and m is 0 or an integer which may be upwards of 10,000. They are prepared by copolymerizing the disiloxanes <FORM:0758168/IV(a)/2> (see Group IV (b)), with diorganosiloxanes, preferably using an alkali metal hydroxide catalyst. Suitable diorganosiloxanes are dimethyl-, phenylmethyl -, stearylmethyl -, cyclohexylmethyl-, chlorophenylmethyl-, bis - trifluorotolyl -, bromo - xenylmethyl -, vinylmethyl -, vinylphenyl-, divinyl-, diphenyl-, ditolyl- and xenylethyl-siloxanes. In the examples: (4) compounds of formula (1) are prepared in which R1 is methyl, n is 2 and m is 1, 2 and 3 and higher, by copolymerizing octamethylcyclotetrasiloxane with the disiloxane of formula (2) wherein n is 2, by heating for 3 days at 80 DEG C. in the presence of KOH; (5) compounds of formula (1) in which one R1 is methyl and the other is phenyl, n is 3 and m is at least 1, are prepared by copolymerizing tetramethyltetraphenyltetrasiloxane with the disiloxane of formula (2) wherein n is 3; (6) compounds of formula (1) in which n is 5, one R1 is methyl and the other is dichlorophenyl and m is at least 1, are obtained by copolymerizing dichlorophenylmethylsiloxane with the disiloxane in which n is 5. Specification 684,295 is referred to.ALSO:The invention comprises organosilyl piperidines of the formula <FORM:0758168/IV(a)/1> where n is from 2 to 5 and R is methyl or phenyl, and siloxanes of the formula <FORM:0758168/IV(a)/2> where R1 is a monovalent hydrocarbon or halogenated aryl hydrocarbon radical and m is O or an integer. The first compounds may be prepared by reacting silylamines of the formula RMe2Si(CH2)nNH2 with pentamethylene dibromide. The disiloxanes (i.e. m = O in formula (2)) are prepared by reacting the compounds of formula (1) with conc. sulphuric acid, treating with water and making alkaline with an alkali metal hydroxide. These disiloxanes may be copolymerized with diorganosiloxanes, preferably using an alkali metal hydroxide catalyst, to give the higher polysiloxanes. In the examples (1) N-(b -trimethylsilylethyl)-piperidine is prepared from pentamethylene dibromide and b -trimethylsilylethylamine; (2) N-(g -trimethylsilylpropyl)-piperidine is similarly prepared; (3) the disiloxane <FORM:0758168/IV(a)/3> is prepared from the product of Example (1) and is copolymerized; (4) with octamethylcyclotetrasiloxane to give polysiloxanes of the formula (2) in which n is 2, m is 1, 2 and 3 and higher and R1 is methyl; (5) the disiloxane is prepared from the product of Example (2) and is copolymerized with tetramethyl-tetra-phenyltetrasiloxane to give compounds of the formula (2) in which one R1 is methyl and the other is phenyl, n is 3 and m is at least 1; (6) N-(5-phenyldimethylsilylpentyl)piperidine is prepared and is converted to the disiloxane which is copolymerized with dichlorophenylmethylsiloxane to give compounds of the formula (2) wherein n is 5, one R1 is methyl and the other is dichlorophenyl, and m is at least 1. Specification 684,295 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US758168XA | 1953-10-28 | 1953-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB758168A true GB758168A (en) | 1956-10-03 |
Family
ID=22128168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25834/54A Expired GB758168A (en) | 1953-10-28 | 1954-09-06 | Organosilicon compounds |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1110557A (en) |
| GB (1) | GB758168A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4762826A (en) * | 1986-04-11 | 1988-08-09 | Ciba-Geigy Corporation | Microbicides |
| US4946880A (en) * | 1986-10-08 | 1990-08-07 | Enichem Synthesis S.P.A. | Silylated U.V. stabilizers containing hindered tertiary amines |
| US5103000A (en) * | 1989-09-13 | 1992-04-07 | Daiso Co., Ltd. | Packing for chromatography and method for separating water soluble organic compounds using the same |
| EP3281958A4 (en) * | 2016-05-03 | 2018-05-16 | LG Chem, Ltd. | Modifying agent, and modified conjugated diene-based polymer produced using same |
-
1954
- 1954-09-06 GB GB25834/54A patent/GB758168A/en not_active Expired
- 1954-10-22 FR FR1110557D patent/FR1110557A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4762826A (en) * | 1986-04-11 | 1988-08-09 | Ciba-Geigy Corporation | Microbicides |
| US4946880A (en) * | 1986-10-08 | 1990-08-07 | Enichem Synthesis S.P.A. | Silylated U.V. stabilizers containing hindered tertiary amines |
| US5103000A (en) * | 1989-09-13 | 1992-04-07 | Daiso Co., Ltd. | Packing for chromatography and method for separating water soluble organic compounds using the same |
| EP3281958A4 (en) * | 2016-05-03 | 2018-05-16 | LG Chem, Ltd. | Modifying agent, and modified conjugated diene-based polymer produced using same |
| US10906995B2 (en) | 2016-05-03 | 2021-02-02 | Lg Chem, Ltd. | Modifier and modified and conjugated diene-based polymer prepared using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1110557A (en) | 1956-02-14 |
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