GB850228A - Improvements in fluorine-containing organosilicon compounds - Google Patents
Improvements in fluorine-containing organosilicon compoundsInfo
- Publication number
- GB850228A GB850228A GB27393/56A GB2739356A GB850228A GB 850228 A GB850228 A GB 850228A GB 27393/56 A GB27393/56 A GB 27393/56A GB 2739356 A GB2739356 A GB 2739356A GB 850228 A GB850228 A GB 850228A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphonyl chloride
- give
- perfluorooctane
- oet
- reacted
- 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
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title abstract 3
- 239000011737 fluorine Substances 0.000 title abstract 3
- 229910052731 fluorine Inorganic materials 0.000 title abstract 3
- 150000003961 organosilicon compounds Chemical class 0.000 title abstract 2
- FJHZKRYJOILIGD-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)S(Cl)(=O)=O FJHZKRYJOILIGD-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 perfluoroalkyl sulphonyl chloride Chemical compound 0.000 abstract 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 239000003999 initiator Substances 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 abstract 1
- TVJHFQWCMCKELZ-UHFFFAOYSA-N 2-fluorooctane Chemical compound CCCCCCC(C)F TVJHFQWCMCKELZ-UHFFFAOYSA-N 0.000 abstract 1
- LLRJCKLNDNKRTF-UHFFFAOYSA-N 5-[2-(2-methoxyphenyl)ethyl]-2-methylbenzene-1,3-diol Chemical compound COC1=CC=CC=C1CCC1=CC(O)=C(C)C(O)=C1 LLRJCKLNDNKRTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 abstract 1
- NWKBSEBOBPHMKL-UHFFFAOYSA-N dichloro(methyl)silane Chemical compound C[SiH](Cl)Cl NWKBSEBOBPHMKL-UHFFFAOYSA-N 0.000 abstract 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000004756 silanes Chemical class 0.000 abstract 1
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- PPDADIYYMSXQJK-UHFFFAOYSA-N trichlorosilicon Chemical compound Cl[Si](Cl)Cl PPDADIYYMSXQJK-UHFFFAOYSA-N 0.000 abstract 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 abstract 1
- 239000011787 zinc oxide Substances 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
- 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 Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Fluorine-containing organosilicon compounds are prepared by reacting a vinyl silane with a perfluoroalkyl sulphonyl chloride or bromide in the presence of a free-radical initiator, with the liberation of sulphur dioxide. The products include the novel compounds having the formula: <FORM:0850228/IV(a)/1> where Rf is a perfluoralkyl radical, X is Cl or Br, R is an alkoxy radical, R1 and R11 are alkyl, alkoxy, fluorine or chlorine, and n is an integer. Specified initiators for the preparation of the silanes are benzoyl peroxide, di-tert-butyl peroxide and ultra-violet light. In the Examples: (1) ViMeSi(OEt)2 is reacted with perfluoromethane sulphonyl chloride to give <FORM:0850228/IV(a)/2> (2) ViMeSiCl2 is reacted with perfluorooctane sulphonyl chloride to give C8F17CH2CHClSiMe Cl2 and <FORM:0850228/IV(a)/3> (3) ViSiCl3 is reacted with perfluorooctane sulphonyl chloride to give C8F17CH2CHClSiCl3 and C8F17CH2CH(SiCl3)CH2CHClSiCl3, and higher telomeric products. (4) ViSi(OEt)3 is used instead of the ViSiCl3 of Example (3), producing the compound of empirical formula C16H18O3 F17ClSi and the 1,2 telomeric product. (5) ViMeSiCl2 is reacted with perfluoromethane sulphonyl chloride to give CF3CH2CHClSiMeCl2 and the 1,2 telomer C7H12F3Cl5Si2. (6) ViMeSi (OEt)2 and perfluorooctane sulphonyl chloride give C8F12CH2CHClSiMe(OEt)2. The compound may be hydrolysed, or polymerized without direct hydrolysis, e.g. by reaction with zinc oxide. In Example (7), the 1,1 adduct of perfluorooctane sulphonyl chloride and ViMeSiCl2 is mixed with MeSiHCl2 and hydrolysed to an oil which is converted to a film by heating at 180 DEG C. A solution in benzotrifluoride is used to treat cotton cloth for water- and oil-repellency. In (8) the adduct as in (7) is cohydrolysed with Me2SiCl2. In (9) the 1,1 and 1,2 adducts of Example (1) are hydrolysed to oils and then polymerized by irradiation with beta rays.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3600559A GB935380A (en) | 1956-09-06 | 1959-10-23 | Saturated fluorocarbon organo silicon compounds and derivatives thereof and methods o making them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US850228XA | 1955-09-06 | 1955-09-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB850228A true GB850228A (en) | 1960-10-05 |
Family
ID=22188945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27393/56A Expired GB850228A (en) | 1955-09-06 | 1956-09-06 | Improvements in fluorine-containing organosilicon compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB850228A (en) |
-
1956
- 1956-09-06 GB GB27393/56A patent/GB850228A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3506674A (en) | Certain pyridyl thio ether silanes | |
| KR830006362A (en) | Method for preparing acid fluoride monomer | |
| US2715113A (en) | Reaction of vinyl silanes with certain perhaloalkanes, the products, and their hydrolysis products | |
| GB850228A (en) | Improvements in fluorine-containing organosilicon compounds | |
| US3678089A (en) | Functional group containing thioether silanes | |
| McBee et al. | The Addition of Trichlorosilane and Methyldichlorosilane to Fluorine-and Chlorinecontaining Olefins | |
| US2965659A (en) | Preparation of fluorine containing organic compounds | |
| US3394162A (en) | Novel compounds and polymers | |
| GB935380A (en) | Saturated fluorocarbon organo silicon compounds and derivatives thereof and methods o making them | |
| McBee et al. | The addition of trichlorosilane and methyldichlorosilane to tetrachloroethylene | |
| GB657443A (en) | Process for the manufacture of organo-silanes | |
| US3269928A (en) | Perfluoroaromatic compounds | |
| ES348858A1 (en) | Improvements in fluorine containing amines | |
| GB695610A (en) | Process of preparing a tetra alkyl or aryl tin | |
| GB669179A (en) | Organo silicon compounds | |
| GB987753A (en) | Catalysts and their use in polymerisation | |
| GB622970A (en) | Improvements in organo-silicon halides | |
| GB1005953A (en) | Improvements in or relating to organo-silicon compounds | |
| US2783275A (en) | Process of preparing vinylsulfofluoride | |
| GB1119577A (en) | Improvements in and relating to tin compounds and siloxane compositions containing same | |
| GB631619A (en) | A process for the manufacture of organo-silicon compounds | |
| GB637739A (en) | Improvements in and relating to the preparation of organo silicon fluorides | |
| GB849061A (en) | Improvements in fluorocarbon-radical-containing organic compounds | |
| GB843795A (en) | Polymers of fluorinated organic compounds | |
| GB865858A (en) | Fluorinated compounds and process for making such compounds |