GB935380A - Saturated fluorocarbon organo silicon compounds and derivatives thereof and methods o making them - Google Patents
Saturated fluorocarbon organo silicon compounds and derivatives thereof and methods o making themInfo
- Publication number
- GB935380A GB935380A GB3600559A GB3600559A GB935380A GB 935380 A GB935380 A GB 935380A GB 3600559 A GB3600559 A GB 3600559A GB 3600559 A GB3600559 A GB 3600559A GB 935380 A GB935380 A GB 935380A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- sicl3
- 9sicl3
- chloro
- fluoro
- 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 Saturated fluorocarbon organo silicon compounds Chemical class 0.000 title abstract 6
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 9
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 239000000460 chlorine Substances 0.000 abstract 5
- PPDADIYYMSXQJK-UHFFFAOYSA-N trichlorosilicon Chemical compound Cl[Si](Cl)Cl PPDADIYYMSXQJK-UHFFFAOYSA-N 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 150000003254 radicals Chemical class 0.000 abstract 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 125000001153 fluoro group Chemical group F* 0.000 abstract 3
- 239000011521 glass Substances 0.000 abstract 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000005827 chlorofluoro hydrocarbons Chemical class 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 229920001296 polysiloxane Polymers 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 2
- IRFCLLARAUQTNK-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(Cl)(=O)=O IRFCLLARAUQTNK-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000005046 Chlorosilane Substances 0.000 abstract 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000443 aerosol Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 abstract 1
- 238000007598 dipping method Methods 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 229910044991 metal oxide Inorganic materials 0.000 abstract 1
- 150000004706 metal oxides Chemical class 0.000 abstract 1
- 150000001451 organic peroxides Chemical class 0.000 abstract 1
- 125000005459 perfluorocyclohexyl group Chemical group 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- 150000004756 silanes Chemical class 0.000 abstract 1
- UQMGAWUIVYDWBP-UHFFFAOYSA-N silyl acetate Chemical class CC(=O)O[SiH3] UQMGAWUIVYDWBP-UHFFFAOYSA-N 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- TTYRJPILQGWBOQ-UHFFFAOYSA-N trichloro(cyclohex-3-en-1-yl)silane Chemical compound Cl[Si](Cl)(Cl)C1CCC=CC1 TTYRJPILQGWBOQ-UHFFFAOYSA-N 0.000 abstract 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/24—Organic compounds containing halogen
- C11D3/245—Organic compounds containing halogen containing fluorine
-
- 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
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/162—Organic compounds containing Si
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Abstract
Coating compositions which impart water-repellency to surfaces comprise solutions of hydrolysable fluorocarbon silanes of the formula <FORM:0935380/III/1> where Rf is a saturated radical containing 1 to 18 carbon atoms each of which forms part of a perfluoroalkyl or perfluorcyclohexyl group, R11 is a trivalent saturated hydrocarbon group of at least 3 carbon atoms, R is alkyl, alkoxy, phenyl, acyloxy, chloro or fluoro, at least one being chloro, fluoro, primary alkoxy or acetoxy, and X is Cl or Br. They may be dissolved in hydrocarbons or chlorofluorohydrocarbons and applied by wiping, dipping or spraying. For example, the compounds CF3(C6H9-Cl)SiCl3 and C4F9(C6H9-Cl)SiCl3 in an aerosol solvent are sprayed on to glass which is heated to 150 DEG C., or on to cold glass which is subsequently polished with a cloth moistened with isopropyl alcohol, and the glass is tested for water- and oil-repellency.ALSO:The invention comprises saturated fluorocarbon silanes of the formula <FORM:0935380/IV(a)/1> where Rf is a saturated radical containing 1 to 18 carbon atoms each of which forms part of a perfluoroalkyl or perfluorocyclohexyl group, R11 is a trivalent saturated hydrocarbon group having at least 3 carbon atoms, R is an alkyl or alkoxy group of up to 5 carbon atoms, or a phenyl, acyloxy, chloro or fluoro radical, at least one R being chloro, fluoro, primary alkoxy or acetoxy, and X is Cl or Br; and also comprises polysiloxanes obtained by their hydrolysis or other polymerization. The silanes are prepared by reacting a silane R1SiR3, where R1 is cyclohexenyl or terminally unsaturated alkenyl having at least 3 carbon atoms, with a fluorocarbon sulphonyl halide in the presence of a free radical generator, SO2 being liberated. The free radicals may be generated by heat, gamma rays, ultra-violet light, organic peroxides and azo compounds. Products containing silicon-bonded chlorine may be further reacted, e.g. with sodium acetate, to produce acetoxy silanes. In the examples: cyclohexenyl trichlorosilane is reacted (1) with perfluorooctyl sulphonyl chloride to give C8F17(C6H9-Cl)SiCl3, (2) with trifluoromethyl sulphonyl chloride to give CF3(C6H9-Cl)SiCl3, and (3) with perfluorobutyl sulphonyl chloride to give C4F9(C6H9-Cl)SiCl3; (4) CH2=CH(CH2)9SiCl3 is reacted with C8F17SO2Br to produce C8F17CH2CHBr(CH2)9SiCl3; (5) CH2=CH(CH2)9SiCl3 and C8F17SO2Cl produce C8F17CH2CHCl(CH2)9SiCl3; (6) CH2=CH(CH2)3Si(C6H5)(CH3)Cl and C4F9SO2Cl produce C4F9CH2CHCl(CH2)3Si(C6H5 (CH3)Cl. The compounds are soluble in volatile liquids, e.g. hydrocarbons and chlorofluorohydrocarbons. Polysiloxanes are obtained by hydrolysis, alone or with other chlorosilanes, or by polymerization, e.g. by reaction with a metal oxide such as ZnO. The polymers may be inert or heat-curable liquids, or solids. Uses: Coatings, lubricants, hydraulic fluids.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB27393/56A GB850228A (en) | 1955-09-06 | 1956-09-06 | Improvements in fluorine-containing organosilicon compounds |
| US76906158A | 1958-10-23 | 1958-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB935380A true GB935380A (en) | 1963-08-28 |
Family
ID=26258786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3600559A Expired GB935380A (en) | 1956-09-06 | 1959-10-23 | Saturated fluorocarbon organo silicon compounds and derivatives thereof and methods o making them |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB935380A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001081515A1 (en) * | 2000-04-26 | 2001-11-01 | Henkel Kommanditgesellschaft Auf Aktien | Washing or cleaning agent |
| US6491838B1 (en) | 1999-11-15 | 2002-12-10 | Degussa Ag | Triamino- and fluoroalkyl-functional organosiloxanes |
| EP2085442A1 (en) | 2008-02-01 | 2009-08-05 | Evonik Degussa GmbH | Compounds containing fluoride with improved surface characteristics |
| DE102008007190A1 (en) | 2008-02-01 | 2009-08-06 | Construction Research & Technology Gmbh | Liquid, fluorine-containing and one-component composition |
| US7611753B2 (en) * | 2002-04-26 | 2009-11-03 | Degussa Ag | Process for impregnating porous mineral substrates |
| EP3744175A1 (en) | 2019-05-31 | 2020-12-02 | Rolex S.A. | Composition for impregnating a substrate, in particular a watchstrap |
-
1959
- 1959-10-23 GB GB3600559A patent/GB935380A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6491838B1 (en) | 1999-11-15 | 2002-12-10 | Degussa Ag | Triamino- and fluoroalkyl-functional organosiloxanes |
| WO2001081515A1 (en) * | 2000-04-26 | 2001-11-01 | Henkel Kommanditgesellschaft Auf Aktien | Washing or cleaning agent |
| US7611753B2 (en) * | 2002-04-26 | 2009-11-03 | Degussa Ag | Process for impregnating porous mineral substrates |
| EP2085442A1 (en) | 2008-02-01 | 2009-08-05 | Evonik Degussa GmbH | Compounds containing fluoride with improved surface characteristics |
| DE102008007190A1 (en) | 2008-02-01 | 2009-08-06 | Construction Research & Technology Gmbh | Liquid, fluorine-containing and one-component composition |
| EP3744175A1 (en) | 2019-05-31 | 2020-12-02 | Rolex S.A. | Composition for impregnating a substrate, in particular a watchstrap |
| EP4140304A1 (en) | 2019-05-31 | 2023-03-01 | Rolex S.A. | Composition for impregnating a substrate, in particular a watchstrap |
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