DE2018516A1 - Tris-triorganosiloxy-chlorophenylsilanes - Google Patents
Tris-triorganosiloxy-chlorophenylsilanesInfo
- Publication number
- DE2018516A1 DE2018516A1 DE19702018516 DE2018516A DE2018516A1 DE 2018516 A1 DE2018516 A1 DE 2018516A1 DE 19702018516 DE19702018516 DE 19702018516 DE 2018516 A DE2018516 A DE 2018516A DE 2018516 A1 DE2018516 A1 DE 2018516A1
- Authority
- DE
- Germany
- Prior art keywords
- tris
- chlorophenylsilanes
- triorganosiloxy
- formula
- methyl radicals
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- -1 tris-trimethylsiloxy-dichlorophenylsilane Chemical compound 0.000 claims description 3
- 150000004756 silanes Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005046 Chlorosilane Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- MCJCREGWRMCHIM-UHFFFAOYSA-N bis(2-butoxycarbonyl-3,4,6-trichlorophenyl) oxalate Chemical compound CCCCOC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1OC(=O)C(=O)OC1=C(Cl)C=C(Cl)C(Cl)=C1C(=O)OCCCC MCJCREGWRMCHIM-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NPVQBEIMNWDKEU-UHFFFAOYSA-N chloromethoxy-dimethoxy-phenylsilane Chemical class ClCO[Si](OC)(OC)C1=CC=CC=C1 NPVQBEIMNWDKEU-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical class CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 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
- 239000012074 organic phase Substances 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical class Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- SPOAMBDEEBRZSZ-UHFFFAOYSA-N trichloro-(2,3,4-trichlorophenyl)silane Chemical compound ClC1=CC=C([Si](Cl)(Cl)Cl)C(Cl)=C1Cl SPOAMBDEEBRZSZ-UHFFFAOYSA-N 0.000 description 1
- NYQDBZQWFXNBRZ-UHFFFAOYSA-N trichloro-(2-chlorophenyl)silane Chemical class ClC1=CC=CC=C1[Si](Cl)(Cl)Cl NYQDBZQWFXNBRZ-UHFFFAOYSA-N 0.000 description 1
- ABADVTXFGWCNBV-UHFFFAOYSA-N trichloro-(4-chlorophenyl)silane Chemical compound ClC1=CC=C([Si](Cl)(Cl)Cl)C=C1 ABADVTXFGWCNBV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
- C09K11/07—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials having chemically interreactive components, e.g. reactive chemiluminescent compositions
-
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
- C10M139/04—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00 having a silicon-to-carbon bond, e.g. silanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/042—Siloxanes with specific structure containing aromatic substituents
- C10M2229/0425—Siloxanes with specific structure containing aromatic substituents used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
Description
in Gen. Vollra (HL-Nr. 52/64) . München, 16.4.70 der Fa. DOW CORNING Corp. Dr. Wg. /Luin Gen. Vollra (HL No. 52/64). Munich, April 16, 1970 from DOW CORNING Corp. Dr. Wg. / Lu
Midland/Mich. (USA) DC 1021/943Midland / Me. (USA) DC 1021/943
Tris-triorganosiloxy-chlorphenylsilaneTris-triorganosiloxy-chlorophenylsilanes
Bei der Oxydation eines chemolumineszenten Materials wird ohne Entwicklung von Hitze Lieht gebildet und diese Erscheinung wird als Chemolumineszenz bezeichnet. Da dieses Licht ohne Einsatz von elektrischen Apparaturen gebildet g When a chemiluminescent material is oxidized, light is formed without generating heat, and this phenomenon is known as chemiluminescence. Since this light is formed without the use of electrical equipment g
wird', genügt es, die Reaktionspartner in einem kleinen, durchsichtigen Behälter zu vermischen. Das Chemolumineszenzlicht ist daher sehr nützlich für Unterwasserarbeiten, in Unterseebooten und in anderen Vorrichtungen, die eine Lichtquelle ohne Hitzeerzeugung und ohne Stromzufuhr benötigen.it is sufficient to mix the reactants in a small, transparent container. The chemiluminescent light is therefore very useful for underwater work, in submarines, and in other devices that require a light source without generating heat and without power supply.
Gegenstand der vorliegenden Erfindung ist daher die Bereitstellung eines Materials, das ein ausgezeichnetes Lösungsmittel für ehemolumineszente Materialien, wie Bis-(2,4,5-trichlor-6-carbobutoxyphenyl)-oxalat ist. Es wurde festgestellt, daß das für ehemolumineszente Materialien verwendbare Lösungsmittel sehr rein sein muß, und daß die erfindungsgemäß beanspruchten Organosiloxane für diesen Zweck außerordentlich -" geeignet sind.The object of the present invention is therefore to provide a material that is an excellent solvent for formerly luminescent materials such as bis (2,4,5-trichloro-6-carbobutoxyphenyl) oxalate is. It has been found to be useful for former luminescent materials Solvent must be very pure, and that the organosiloxanes claimed according to the invention for this purpose extraordinarily - " are suitable.
Erfindungsgemäß werden Tris-triorganosiloxy-chlorphenylsilane der Formel C1x~C6H5-x " SAccording to the invention, triorganosiloxy-chlorophenylsilanes of the formula C1 x ~ C 6 H 5-x "S
worin R Phenyl- oder Methylreste bedeutet und χ 1,2,3 oder 4 ist, beansprucht.where R is phenyl or methyl radicals and χ is 1, 2, 3 or 4, claimed.
ti·ti
Diese Verbindungen können am besten durch Mischhydrolyse von Methoxysilanen der FormelThese compounds can best be obtained by mixed hydrolysis of Methoxysilanes of the formula
mit Chlorsilanen der Formelwith chlorosilanes of the formula
hergestellt werden. Die so erhaltenen Produkte werden anschließend ggf. durch Destillation gereinigt, damit das Endprodukt den geforderten Reinheitsbedingungen entspricht.getting produced. The products thus obtained are then if necessary purified by distillation so that the end product meets the required purity conditions.
Die hierbei als Ausgangsprodukte eingesetzten Chlorphenyltrimethoxysilane können durch Umsetzung der entsprechenden Chlorphenyltrichlorsilane mit Methanol hergestellt werden. Die Chlorphenyltrietilorsilane können durch Reaktion von Phenyltrichlorsilanen mit Chlor in Gegenwart von Eisen nach üblichen Chlorierungsverfahren für Benzolkerne gewonnen werden. Das Ausmaß der Chlorierung hängt hierbei selbstverständlich von dem Mol-Verhältnis Chlor zu Phenyl ab, sowie von der Reaktionszeit und der Reaktionstemperatur. Ggf. können die chlorierten Phenyltriehlorsilane destilliert werden, um solche von unterschiedlichem Chlorierungsgrad zu trennen, das sind Monochlorphenyltriehlorsilan, Dieftlorphenyltrichlorsilan, Trichlorphenyltrichlorsilan und Tetraehlorphenyltrichlorsilan. Zur Herstellung der erfindungsgemäß beanspruchten Verbindungen · können jedoch auch Gemische aus diesen Chlorierungsprodukten eingesetzt werden. The chlorophenyltrimethoxysilanes used as starting materials here can be prepared by reacting the corresponding chlorophenyltrichlorosilanes with methanol. The chlorophenyltrietilorsilanes can be obtained by reacting phenyltrichlorosilanes with chlorine in the presence of iron using conventional chlorination processes for benzene nuclei. The extent of the chlorination depends of course on the molar ratio of chlorine to phenyl, as well as on the reaction time and the reaction temperature. If necessary, the chlorinated phenyltriehlorsilanes can be distilled in order to separate those with different degrees of chlorination, these are monochlorophenyltrichlorosilane, dieftlorophenyltrichlorosilane, trichlorophenyltrichlorosilane and tetraehlorphenyltrichlorosilane. However, mixtures of these chlorination products can also be used to prepare the compounds claimed according to the invention.
Die als Ausgangsprodukte verwendeten Triorganochlorsilane sind Trimethylchloreilan, Phenyldimethylehlorsllan oder Diphenylmethyl< chlorsllan. Diese Chlorsilane können einzeln oder im Gemisch für die Mischhydrolyse eingesetzt werden.The triorganochlorosilanes used as starting materials are Trimethylchloroilane, Phenyldimethylehlorsllane or Diphenylmethyl < chlorosllan. These chlorosilanes can be used individually or in a mixture for the mixed hydrolysis.
Die erfindungsgemäi beanspruchten Verbindungen sind außerdem wertvolle Schmiermittel und Hydrauliköle»The compounds claimed according to the invention are also valuable lubricants and hydraulic oils »
1 Mol Dichlorphenyltriehlorsilan wurde bei Raumtemperatur mit 3,2 Mol Methanol versetzt unter Entweichen des gebildeten Chlorwasserstoffes. Anschließend wurden 4,5 Mol Methyltrichlorsilan zugefügt und die Mischung in einem Eisbad, unter langsamer Zugabe von 12,5 Mol Wasser, gekühlt. Das Hydrolysat wurde eine Stunde gerührt. Dann wurde die organische Phase abgetrennt und mit Wasser gewaschen, bis sie neutral reagierte. Das Hexamethyldisiloxan wurde im Vakuum abgezogen und der Rückstand destilliert. Es wurde Tris-trimethylsiloxydichlorphenylsilan erhalten, das folgende Eigenschaften hatte: |1 mole of dichlorophenyltriehlorsilane was at room temperature with 3.2 mol of methanol are added with the escape of the hydrogen chloride formed. Then 4.5 moles of methyltrichlorosilane were added and the mixture in an ice bath, with slow addition of 12.5 moles of water, cooled. The hydrolyzate became a Hour stirred. The organic phase was then separated off and washed with water until it reacted neutrally. The hexamethyldisiloxane was stripped off in vacuo and the residue was distilled. Tris-trimethylsiloxydichlorophenylsilane was obtained which had the following properties: |
n2^ 1,4599* D 25°C 1,048 ,spezifische Refraktion 0,26l,Viskosität 9,1 cSt./25°C und Siedepunkt 297°C bei 7^6 mm Hg.n 2 ^ 1.4599 * D 25 ° C 1.048, specific refraction 0.26 l, viscosity 9.1 cSt./25 ° C and boiling point 297 ° C at 7 ^ 6 mm Hg.
Durch Einsatz folgender Methoxy- und Chlorsilane in dem VerfahrenBy using the following methoxy and chlorosilanes in the process
gemäß Beispiel 1 wurden folgende Verbindungen erhalten: -according to example 1 the following compounds were obtained:
/■j \l6h^;2üii3öio± 01L6H4OiLUbIvU6H5^2Uw3J3 / ■ j \ l 6 h ^; 2 üii 3 öio ± 01L 6 H 4 OiLUbIvU 6 H 5 ^ 2 Uw 3 J 3
(OCH,), OrHc(CH,)oSiCl 01,C^-H0Si [ OSi (C^-H1-)'(CH,) o L *(OCH,), OrH c (CH,) o SiCl 01, C ^ -H 0 Si [OSi (C ^ -H 1 -) '(CH,) o L *
3 3 "53^ 3o2 dd3 ^a3 3 "53 ^ 3o2 dd3 ^ a
Cl4C6HSi(OCH ), (CH,),SiClCl 4 C 6 HSi (OCH), (CH,), SiCl
Die gemäß Beispiel 1 und 2 hergestellten Tris-triorganosiloxychlorphenylsilane wurden als Lösungsmittel für Bis-(2,4,5-trichlor-6-carbobutoxyphenyl)-oxalat getestet, und es wurde gefunden, daß sie ausgezeichnete, stabile Lösungen ergeben, die als chemolumineszente Lichtquellen brauchbar sind.The triorganosiloxychlorophenylsilanes prepared according to Examples 1 and 2 were used as a solvent for bis (2,4,5-trichloro-6-carbobutoxyphenyl) oxalate tested and found to give excellent, stable solutions that are chemiluminescent Light sources are usable.
009846/1943009846/1943
Claims (5)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81714969A | 1969-04-17 | 1969-04-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2018516A1 true DE2018516A1 (en) | 1970-11-12 |
Family
ID=25222439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702018516 Pending DE2018516A1 (en) | 1969-04-17 | 1970-04-17 | Tris-triorganosiloxy-chlorophenylsilanes |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE749040A (en) |
| DE (1) | DE2018516A1 (en) |
| FR (1) | FR2043389A5 (en) |
| GB (1) | GB1241788A (en) |
-
1970
- 1970-03-17 GB GB02726/70A patent/GB1241788A/en not_active Expired
- 1970-04-15 FR FR7013601A patent/FR2043389A5/fr not_active Expired
- 1970-04-16 BE BE749040D patent/BE749040A/en unknown
- 1970-04-17 DE DE19702018516 patent/DE2018516A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE749040A (en) | 1970-10-16 |
| GB1241788A (en) | 1971-08-04 |
| FR2043389A5 (en) | 1971-02-12 |
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