DE1053787B - Verfahren zur Herstellung von fluorhaltigen Organosiloxanen - Google Patents
Verfahren zur Herstellung von fluorhaltigen OrganosiloxanenInfo
- Publication number
- DE1053787B DE1053787B DED26321A DED0026321A DE1053787B DE 1053787 B DE1053787 B DE 1053787B DE D26321 A DED26321 A DE D26321A DE D0026321 A DED0026321 A DE D0026321A DE 1053787 B DE1053787 B DE 1053787B
- Authority
- DE
- Germany
- Prior art keywords
- cch
- formula
- silanes
- hydrolysis
- grignard reagent
- 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
- 125000005375 organosiloxane group Chemical group 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title description 2
- 229910052731 fluorine Inorganic materials 0.000 title description 2
- 239000011737 fluorine Substances 0.000 title description 2
- -1 siloxanes Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000007818 Grignard reagent Substances 0.000 claims description 10
- 150000004795 grignard reagents Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- 150000004756 silanes Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SAUGMJLWYLQPEM-UHFFFAOYSA-N 3-bromo-1,1,1-trifluoropropane Chemical compound FC(F)(F)CCBr SAUGMJLWYLQPEM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDWQLICBSFIDRM-UHFFFAOYSA-N 1,1,1-trifluoropropane Chemical compound CCC(F)(F)F KDWQLICBSFIDRM-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001367 organochlorosilanes Chemical class 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C07F7/12—Organo silicon halides
-
- 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
- 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
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/01—Silicones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Silicon Polymers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US606572A US2927870A (en) | 1956-08-28 | 1956-08-28 | Zirconium acetate-zinc acetate catalyzed organohydrogenosiloxane emulsions and the treatment of fabrics therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1053787B true DE1053787B (de) | 1959-03-26 |
Family
ID=24428511
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED26321A Pending DE1053787B (de) | 1956-08-28 | 1957-08-28 | Verfahren zur Herstellung von fluorhaltigen Organosiloxanen |
| DED26319A Pending DE1178397B (de) | 1956-08-28 | 1957-08-28 | Verfahren zum Hydrophobieren von Fasergut |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED26319A Pending DE1178397B (de) | 1956-08-28 | 1957-08-28 | Verfahren zum Hydrophobieren von Fasergut |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2927870A (OSRAM) |
| BE (2) | BE560351A (OSRAM) |
| DE (2) | DE1053787B (OSRAM) |
| FR (2) | FR1179745A (OSRAM) |
| GB (2) | GB809766A (OSRAM) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3050485A (en) * | 1957-07-27 | 1962-08-21 | Wacker Chemie Gmbh | Method for curing organopolysiloxane compositions with sulfur-containing compounds which are reducible by nascent hydrogen |
| DE1186025B (de) * | 1959-05-16 | 1965-01-28 | Rotta Chem Fab Theodor | Verfahren zur Hydrophobierung von Textilien mit waessrigen stabilen emulgator- und schutzkolloidfreien Silikon-Emulsionen |
| BE592727A (OSRAM) * | 1959-07-07 | |||
| DE1200987B (de) * | 1960-08-24 | 1965-09-16 | Dow Corning | Wasserabstossend machendes, lufttrocknendes UEberzugsmittel |
| DE1215929B (de) * | 1960-08-26 | 1966-05-05 | Wacker Chemie Gmbh | Stabilisatoren fuer waessrige Emulsionen, die Organowasserstoffpolysiloxane enthalten |
| US3350337A (en) * | 1962-03-14 | 1967-10-31 | Dow Corning | Finish for glass cloth |
| DE1266496B (de) * | 1963-06-15 | 1968-04-18 | Bayer Ag | Organopolysiloxan-Emulsionen |
| BE602682A (fr) * | 1964-02-19 | 1961-10-17 | Hoechst Ag | Durcissants pour organo-polysiloxanes |
| US3395036A (en) * | 1965-05-17 | 1968-07-30 | Dow Corning | Process for post-finishing pigmented glass fabric |
| US3442817A (en) * | 1966-04-15 | 1969-05-06 | Du Pont | Preparation of zirconia and hafnia sols |
| CH1246067D (OSRAM) * | 1966-10-06 | |||
| GB1502265A (en) * | 1974-05-28 | 1978-03-01 | Dow Corning Ltd | Treatment of fibres |
| GB1532898A (en) * | 1974-08-12 | 1978-11-22 | Very Important Prod Inc | Preservative composition for preserving and renewing surfaces |
| US4122107A (en) * | 1976-03-26 | 1978-10-24 | M&T Chemicals Inc. | Reaction products of specific antimony compounds with a carboxylate of zinc calcium or manganese and an alcohol or glycol |
| DE3113365A1 (de) * | 1980-04-08 | 1982-04-15 | Dow Corning Ltd., London | Waessrige beschichtungsmasse |
| US4306990A (en) * | 1980-07-18 | 1981-12-22 | Edward Goodman | Cleaning and protective composition and method |
| DE69129145T2 (de) | 1990-12-25 | 1998-07-16 | Matsushita Electric Ind Co Ltd | Transparentes Substrat mit aufgebrachtem monomolekularem Film und Verfahren zu seiner Herstellung |
| US6503567B2 (en) | 1990-12-25 | 2003-01-07 | Matsushita Electric Industrial Co., Ltd. | Transparent substrate and method of manufacturing the same |
| EP0493747B1 (en) * | 1990-12-25 | 1996-07-10 | Matsushita Electric Industrial Co., Ltd. | Anti-contaminating adsorbed film and method of manufacturing the same |
| JPH0616813A (ja) * | 1992-06-29 | 1994-01-25 | Toray Dow Corning Silicone Co Ltd | フルオロシリコ−ンポリマ−およびその製造方法 |
| DE10020332A1 (de) * | 2000-04-26 | 2001-11-15 | Henkel Kgaa | Wasch- und Reinigungsmittel |
| SE543744C2 (en) | 2019-12-13 | 2021-07-06 | Organowood Ab | New wood protecting methods and wood products produced with the methods |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2743192A (en) * | 1956-04-24 | He same | ||
| US2588393A (en) * | 1952-03-11 | Organosiloxane coating composition | ||
| BE498183A (OSRAM) * | 1949-11-10 | 1900-01-01 | ||
| US2588366A (en) * | 1950-03-09 | 1952-03-11 | Dow Corning | Method of rendering fabrics waterrepellent and composition therefor |
| US2687388A (en) * | 1950-11-13 | 1954-08-24 | Nat Distillers Prod Corp | Phenyl methyl siloxane solution containing a zirconium salt |
| BE523009A (OSRAM) * | 1952-09-23 | |||
| US2718483A (en) * | 1953-02-03 | 1955-09-20 | Dow Corning | Siloxane resins containing methyl and phenyl bonded to silicon and laminates |
| US2728692A (en) * | 1953-04-20 | 1955-12-27 | Dow Corning | Method of preventing shrinkage of wool |
| US2735791A (en) * | 1953-08-05 | 1956-02-21 | Waterproofing compositions and their | |
| US2798858A (en) * | 1954-02-08 | 1957-07-09 | Gen Electric | Treatment of leather with methylpolysiloxanes |
| BE536477A (OSRAM) * | 1954-03-15 | 1900-01-01 | ||
| US2803614A (en) * | 1954-03-15 | 1957-08-20 | Gen Electric | Tin compound as a curing agent for organopolysiloxanes |
-
1956
- 1956-08-28 US US606572A patent/US2927870A/en not_active Expired - Lifetime
-
1957
- 1957-06-21 GB GB19648/57A patent/GB809766A/en not_active Expired
- 1957-06-26 GB GB20203/57A patent/GB805028A/en not_active Expired
- 1957-07-23 FR FR1179745D patent/FR1179745A/fr not_active Expired
- 1957-08-09 FR FR1181027D patent/FR1181027A/fr not_active Expired
- 1957-08-27 BE BE560351D patent/BE560351A/fr unknown
- 1957-08-27 BE BE560350D patent/BE560350A/xx unknown
- 1957-08-28 DE DED26321A patent/DE1053787B/de active Pending
- 1957-08-28 DE DED26319A patent/DE1178397B/de active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB809766A (en) | 1959-03-04 |
| US2927870A (en) | 1960-03-08 |
| BE560350A (OSRAM) | 1957-09-14 |
| DE1178397B (de) | 1964-09-24 |
| BE560351A (OSRAM) | 1957-09-14 |
| GB805028A (en) | 1958-11-26 |
| FR1181027A (fr) | 1959-06-11 |
| FR1179745A (fr) | 1959-05-27 |
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