GB802359A - Improvements in or relating to vulcanisable compositions and elastomeric compositions - Google Patents
Improvements in or relating to vulcanisable compositions and elastomeric compositionsInfo
- Publication number
- GB802359A GB802359A GB617/57A GB61757A GB802359A GB 802359 A GB802359 A GB 802359A GB 617/57 A GB617/57 A GB 617/57A GB 61757 A GB61757 A GB 61757A GB 802359 A GB802359 A GB 802359A
- Authority
- GB
- United Kingdom
- Prior art keywords
- give
- reacting
- copolymer
- formula
- silane
- 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
- 239000000203 mixture Substances 0.000 title abstract 8
- -1 perfluoroalkyl radical Chemical group 0.000 abstract 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 9
- 229920001577 copolymer Polymers 0.000 abstract 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 4
- 150000001336 alkenes Chemical class 0.000 abstract 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 4
- 229910000077 silane Inorganic materials 0.000 abstract 4
- 239000000377 silicon dioxide Substances 0.000 abstract 4
- 239000000945 filler Substances 0.000 abstract 3
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 2
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 abstract 2
- 150000007942 carboxylates Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- BUMGIEFFCMBQDG-UHFFFAOYSA-N dichlorosilicon Chemical compound Cl[Si]Cl BUMGIEFFCMBQDG-UHFFFAOYSA-N 0.000 abstract 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000003517 fume Substances 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 230000005855 radiation Effects 0.000 abstract 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 101001001462 Homo sapiens Importin subunit alpha-5 Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 102100036186 Importin subunit alpha-5 Human genes 0.000 abstract 1
- 239000005909 Kieselgur Substances 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- UCJIVFREPMUZDC-UHFFFAOYSA-M [Br-].CC(C)[Mg+] Chemical class [Br-].CC(C)[Mg+] UCJIVFREPMUZDC-UHFFFAOYSA-M 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000006229 carbon black Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 238000010292 electrical insulation Methods 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 239000000446 fuel Substances 0.000 abstract 1
- 239000003365 glass fiber Substances 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 239000005337 ground glass Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 230000001050 lubricating effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- PPDADIYYMSXQJK-UHFFFAOYSA-N trichlorosilicon Chemical compound Cl[Si](Cl)Cl PPDADIYYMSXQJK-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910001928 zirconium oxide Inorganic materials 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A vulcanizable composition comprises: (1) a copolymer consisting essentially of (a) 75 mol. per cent or less of a siloxane having the unit formula <FORM:0802359/IV (a)/1> in which each R is a perfluoroalkyl radical, n is 1 or 2, each R1 is a monovalent hydrocarbon radical and m is 0 or 1, and (b) at least 25 mol. per cent of a siloxane of the unit formula R112SiO, in which each R11 is a monovalent hydrocarbon radical, sufficient amount of (a) being present to give at least 10 per cent by weight of fluorine in the copolymer; (2) a filler; and (3) a vulcanizing agent. Each R1 and R11 may be an alkyl, alkenyl, cycloaliphatic, aralkyl or aryl radical. Fillers specified are silica, fume silica, diatomaceous earth, clay, ground glass, glass fibres, carbon black, titania and zinc, ferric, chromic and zirconium oxides, and they may be modified by having, e.g. trimethylsiloxy, ethoxy or isopropoxy groups attached to the surfaces thereof. The filler may be used in amount from 10 to 200 parts (by weight) per 100 parts of copolymer. The composition may be vulcanized by radiation, such as X-rays, or with benzoyl, 2:4-dichloro-benzoyl or cumyl peroxide, tertiary butyl paracetate; mixtures of polysilicates and metal carboxylates; and mixtures of hydrogen-containing siloxanes and metal carboxylates or chloroplatinic acid. In examples: (1) a copolymer was made by reacting the silane C3H7CH2.CH2.Si.CH3.Cl2 with conc. H2SO4 until evolution ceased, stirring in dimethyl-siloxane (cyclic tetramer) until equilibrium was reached, adding water to hydrolyse the Sibonded sulphate groups and purifying and isolating the liquid polymer; the polymer was then mixed with fume silica and benzoyl peroxide and cured at 150 DEG C; (2) the silane C7F15.CH2.CH2-Si.CH3Cl2 was co-hydrolysed with (CH3)2.SiCl2 and the resulting copolymer was milled with silica and benzoyl peroxide and cured; (3) the copolymer was made and cured as in (2); (4), (5), (6) the copolymers were made as in (1) and cured with acyl peroxides or by electron radiation. Uses.-As gaskets and hoses in fuel, hydraulic and lubricating systems for automotive vehicles, and as electrical insulation. The perfluoroalkyl-silanes used in making the above copolymers may be made (1) by reacting an olefin of the formula RCH=CH2 with a silane of the formula R1mSiHnCl4-n-m, wherein R, R1, m and n are as above defined; or (2) by reacting the olefin RCH=CH2 with HBr to give RCH2.CH2Br and thereafter preparing a Grignard reagent of this compound which can then be reacted with the silane R1mSiCl4-m. In examples, (1) the olefin C3H7CH=CH2 was reacted with CH3.H.SiCl2 in an autoclave at 250 DEG C. to give <FORM:0802359/IV (a)/2> ; (2) <FORM:0802359/IV (a)/3> Cl2 were made by the process of (1); (5) (C3F7CH2.CH2)2SiCl2 was made by reacting C3F7CH=CH2 with H2SiCl2; (6) (C3F7CH2.CH2) CH2=CHSiCl2 was made by reacting C3F7CH2. CH2Br with CH2=CH.SiCl3 in ether. Specifications 760,201 and 802,358 are referred to.ALSO:Olefinic compounds of the formula RCH= CH2, wherein R is a perfluoroalkyl radical, may be made by esterifying a perfluoro acid R.COOH with ethanol and reacting the resulting ester with a mixture of an isopropyl Grignard and a methyl Grignard to give an alcohol of the formula R(CH3)CH.OH, which is then dehydrated by heating with P2O5 to give the required olefin. In examples: (1) C3F7COOH was esterified with ethanol and the ester was then reacted in ether with a mixture of methyl and isopropyl magnesium bromides to give C3F7(CH3)CHOH and propylene. The alcohol was then dehydrated with P2O5 to give C3F7CH=CH2; (2) C7F15CH=CH2\t was made in a similar manner.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1173261XA | 1956-04-02 | 1956-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB802359A true GB802359A (en) | 1958-10-01 |
Family
ID=22372263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB617/57A Expired GB802359A (en) | 1956-04-02 | 1957-01-07 | Improvements in or relating to vulcanisable compositions and elastomeric compositions |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1113567B (en) |
| FR (1) | FR1173261A (en) |
| GB (1) | GB802359A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1128651B (en) * | 1958-12-29 | 1962-04-26 | Dow Corning A G | Compounds that can be hardened to form elastomers based on fluorine-containing organosiloxane copolymers, fillers and hardeners |
| US3503926A (en) * | 1968-05-17 | 1970-03-31 | Dow Corning | Solid lubricant composition |
| US4736048A (en) * | 1986-06-04 | 1988-04-05 | Dow Corning Corporation | Pressure sensitive adhesive release liner and fluorosilicone compounds, compositions and method therefor |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4355121A (en) * | 1981-04-09 | 1982-10-19 | General Electric Company | Heat strength curable silicone rubber compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE527843A (en) * | 1953-04-03 | |||
| DE966458C (en) * | 1953-04-03 | 1957-08-08 | Gen Electric | Vulcanizable organopolysiloxane compound, especially for the production of moldings |
-
1957
- 1957-01-07 GB GB617/57A patent/GB802359A/en not_active Expired
- 1957-03-21 FR FR1173261D patent/FR1173261A/en not_active Expired
- 1957-03-28 DE DED25263A patent/DE1113567B/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1128651B (en) * | 1958-12-29 | 1962-04-26 | Dow Corning A G | Compounds that can be hardened to form elastomers based on fluorine-containing organosiloxane copolymers, fillers and hardeners |
| US3503926A (en) * | 1968-05-17 | 1970-03-31 | Dow Corning | Solid lubricant composition |
| US4736048A (en) * | 1986-06-04 | 1988-04-05 | Dow Corning Corporation | Pressure sensitive adhesive release liner and fluorosilicone compounds, compositions and method therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1113567B (en) | 1961-09-07 |
| FR1173261A (en) | 1959-02-23 |
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