GB746510A - Improvements in or relating to fluorine-containing silanes and siloxanes - Google Patents

Improvements in or relating to fluorine-containing silanes and siloxanes

Info

Publication number
GB746510A
GB746510A GB26748/53A GB2674853A GB746510A GB 746510 A GB746510 A GB 746510A GB 26748/53 A GB26748/53 A GB 26748/53A GB 2674853 A GB2674853 A GB 2674853A GB 746510 A GB746510 A GB 746510A
Authority
GB
United Kingdom
Prior art keywords
trichlorosilane
prepared
dichlorosilane
tetrafluoroethyl
trifluorovinyl
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
Application number
GB26748/53A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Midland Silicones Ltd
Original Assignee
Midland Silicones Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Midland Silicones Ltd filed Critical Midland Silicones Ltd
Publication of GB746510A publication Critical patent/GB746510A/en
Expired legal-status Critical Current

Links

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
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-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 System
    • 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 System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/12—Organo silicon halides
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/46—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes silicones

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)

Abstract

The invention comprises polysiloxanes having the unit formula <FORM:0746510/IV(a)/1> where R is a trifluorovinyl, tetrafluorethyl, hexafluro-butenyl, hexafluoropropyl, octafluoroethyl, chlorodifluorovinyl, chlorohexafluorocyclopentenyl, chloro-octafluorocyclohexenyl or chlorotrifluorethyl radical, R1 is a monovalent hydrocarbon radical, n is 1 or 2, z is 0, 1 or 2, and (n + z) is not greater than 3; and also copolymers of these siloxanes with each other and with other siloxanes. The homopolymers are prepared by hydrolysing a chlorosilane of the formula RnR1z Si Cl4-(n + z) and condensing. The examples describe the preparation of polysiloxanes having the unit formula (1) HCF2CO2 SiO1\ml5, (2) (HCF2CF2)2SiO, (3) CF3CFHCF2 SiO1\ml5, (4) (CF3CFHCF2)2SiO, (5) CF2 = CFCHFCF2SiO1\ml5, (6) ClFHCCF2SiO1\ml5, F2HC.C.ClFSiO1\ml5 and (CF2 = CF)SiO1\ml5, (7) CF3CF2CFHCF2SiO1\ml5, (8) (CF2HCF2)(C6H5)2 <FORM:0746510/IV(a)/2> (9) (FCl.C = CF)CH3SiO, (10) ClFC = CFSiO1\ml5, (11) <FORM:0746510/IV(a)/3> (12) F2C = CF)CH3SiO, (13) F2C = CFSiO1\ml5, (14) <FORM:0746510/IV(a)/4> The materials are useful as coating compositions, electrical insulation, lubricants and hydraulic fluids.ALSO:The invention comprises silanes of the formula RnR1mSiCl4-(m+n), where R is a trifluorovinyl, tetrafluoroethyl, hexafluoro-propyl, hexafluorobutenyl, octafluorobutyl, chlorodifluorovinyl, chlorohexafluorocyclopentenyl, chloro-octafluorocyclohexenyl or chlorotrifluoroethyl radical, R1 is a monovalent hydrocarbon radical, n is 1 or 2, m is 0, 1, 2 or 3, and (m+n) is not greater than 4. The fluorine radicals, when n is 2, may be the same or different. The compounds, when m is 0, are best prepared by heating, at temperatures of 150 DEG to 600 DEG C., the corresponding unsaturated fluorocarbon with di- or tri-chlorosilane. Autogenous pressure favours the production of compounds containing saturated fluorocarbon radicals, atmospheric pressure favours the production of unsaturated compounds. The compounds containing hydrocarbon radicals may be prepared (a) by reacting the fluorocarbon silane with a Grignard reagent, or (b) by reacting the unsaturated fluorocarbon with a silane of the formula R1xHySiCl4-(x+y), where x and y each are from 1 to 3 and their sum is not greater than 4, if desired in the presence of a catalyst, e.g. boron trichloride or trifluoride. The compounds, which are useful as coating compositions, electrical insulation, lubricants and hydraulic fluids, may be converted to siloxanes by the usual methods (see Group IV (a)). In the examples: (1) tetrafluoroethyl trichlorosilane is prepared from trichlorosilane and tetrafluoroethylene; (2) bis-tetrafluoroethyl dichlorosilane is similarly prepared from dichlorosilane and tetrafluoroethylene; (3) hexafluoropropyl trichlorosilane is obtained from trichlorosilane and perfluoropropylene; and (4), using dichlorosilane, bis-hexafluoropropyl dichlorosilane is obtained; (5) hexafluorobutenyl-3-trichlorosilane is prepared from trichlorosilane and perfluorobutadiene; (6) trichlorosilane and chlorotrifluoroethylene yield a mixture of isomeric trifluorochloroethyl trichlorosilanes and trifluorovinyl trichlorosilane; (7) octafluorobutyl trichlorosilane is prepared from perfluorobutylene and trichlorosilane; (8) a mixture of tetrafluoroethyl phenyl dichlorosilane and tetrafluoroethyl diphenyl chlorosilane is obtained by reacting tetrafluoroethyl trichlorosilane with phenyl magnesium bromide in diethyl ether; (9) beta-chlorodifluorovinyl methyl dichlorosilane is prepared from dichlorodifluoroethylene and methyl-dichlorosilane; and (10), using trichlorosilane, beta-chlorodifluorovinyl trichlorosilane is obtained; (11) 2-chloro-3,3-4,4-5,5-hexafluorocyclopent-1-enyl methyl dichlorosilane is prepared from 1,2-dichloro-3,3-4,4-5,5-hexafluorocyclopent-1-ene and methyldichlorosilane; (12) trifluorovinyl methyl dichlorosilane is prepared from methyl-dichlorosilane and chlorotrifluoroethylene; and (13), using trichlorosilane, trifluorovinyl trichlorosilane is obtained; (14) 2-chloro-3,3-4,4-5,5-6,6-octafluorocyclohex-1-enyl phenyl dichlorosilane is prepared from phenyl-dichlorosilane and 1,2-dichloro - 3,3 - 4,4 - 5,5 - 6,6 - octafluorocyclohex-1-ene; (15) trimethyl hexafluoropropylsilane is prepared from perfluoropropylene and trimethylsilane. The trimethylsilane is prepared by reducing trimethylchlorosilane with lithium aluminium hydride in diethyl ether.
GB26748/53A 1952-11-17 1953-09-29 Improvements in or relating to fluorine-containing silanes and siloxanes Expired GB746510A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US746510XA 1952-11-17 1952-11-17

Publications (1)

Publication Number Publication Date
GB746510A true GB746510A (en) 1956-03-14

Family

ID=22120808

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26748/53A Expired GB746510A (en) 1952-11-17 1953-09-29 Improvements in or relating to fluorine-containing silanes and siloxanes

Country Status (3)

Country Link
DE (1) DE1022225B (en)
FR (1) FR1090847A (en)
GB (1) GB746510A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6503567B2 (en) 1990-12-25 2003-01-07 Matsushita Electric Industrial Co., Ltd. Transparent substrate and method of manufacturing the same
US6521334B1 (en) 1990-12-25 2003-02-18 Matsushita Electric Industrial Co., Ltd. Transparent substrate and method of manufacturing the same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1118620A (en) * 1954-02-05 1956-06-08 Bayer Ag Process for the production of organic compounds containing silicon and halogen
US3012006A (en) * 1958-04-24 1961-12-05 Dow Corning Fluorinated alkyl silanes and their use

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB684597A (en) * 1946-06-27 1952-12-24 Montclair Res Corp Improvements in or relating to the preparation of organo silicon derivatives from unsaturated compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6503567B2 (en) 1990-12-25 2003-01-07 Matsushita Electric Industrial Co., Ltd. Transparent substrate and method of manufacturing the same
US6521334B1 (en) 1990-12-25 2003-02-18 Matsushita Electric Industrial Co., Ltd. Transparent substrate and method of manufacturing the same

Also Published As

Publication number Publication date
FR1090847A (en) 1955-04-04
DE1022225B (en) 1958-01-09

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