GB766528A - A process for the production of organosilicon compounds - Google Patents
A process for the production of organosilicon compoundsInfo
- Publication number
- GB766528A GB766528A GB9286/55A GB928655A GB766528A GB 766528 A GB766528 A GB 766528A GB 9286/55 A GB9286/55 A GB 9286/55A GB 928655 A GB928655 A GB 928655A GB 766528 A GB766528 A GB 766528A
- Authority
- GB
- United Kingdom
- Prior art keywords
- product
- fractionated
- silicon
- reacting
- 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
- 150000003961 organosilicon compounds Chemical class 0.000 title abstract 5
- -1 polymers Chemical class 0.000 abstract 15
- 239000004205 dimethyl polysiloxane Substances 0.000 abstract 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 abstract 5
- 229920001296 polysiloxane Polymers 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 abstract 3
- 229910052710 silicon Inorganic materials 0.000 abstract 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 abstract 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 abstract 2
- 244000043261 Hevea brasiliensis Species 0.000 abstract 2
- 239000005062 Polybutadiene Substances 0.000 abstract 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001336 alkenes Chemical class 0.000 abstract 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 229920003052 natural elastomer Polymers 0.000 abstract 2
- 229920001194 natural rubber Polymers 0.000 abstract 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 2
- 229920002857 polybutadiene Polymers 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 239000010703 silicon Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- ABPBVCKGWWGZDP-UHFFFAOYSA-N 1,2-dichloro-3,3,4,4,5,5-hexafluorocyclopentene Chemical compound FC1(F)C(Cl)=C(Cl)C(F)(F)C1(F)F ABPBVCKGWWGZDP-UHFFFAOYSA-N 0.000 abstract 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-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
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229920000459 Nitrile rubber Polymers 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 abstract 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- KFUSEUYYWQURPO-UPHRSURJSA-N cis-1,2-dichloroethene Chemical group Cl\C=C/Cl KFUSEUYYWQURPO-UPHRSURJSA-N 0.000 abstract 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 abstract 1
- 229940069096 dodecene Drugs 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000001050 lubricating effect Effects 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 230000000704 physical effect Effects 0.000 abstract 1
- 229920001084 poly(chloroprene) Polymers 0.000 abstract 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- 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
- C07F7/0801—General processes
-
- 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
- C07F7/0872—Preparation and treatment thereof
- C07F7/0889—Reactions not involving the Si atom of the Si-O-Si sequence
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
Abstract
766,528. Organo-silicon compounds and polymers. MIDLAND SILICONES, Ltd. March 30, 1955 [April 13, 1954], No. 9286/55. Classes 2 (6) and 2 (7). [Also in Group V] Organo-silicon compounds, including polymers, free from aliphatic unsaturation and silicon-bonded hydrogen and containing at least one alkyl radical of less than five carbon atoms attached to silicon, are modified by reaction with an olefinic compound in the presence of an aromatic acyl peroxide. It is suggested that a hydrogen atom is abstracted from the alkyl radical followed by addition of the olefine to the free radical thus produced. The olefine may polymerize under the influence of the peroxide and the. temperature should therefore be kept below that at which such polymerization occurs rapidly. Temperatures of 50-75 C. are specified for the more reactive olefinic compounds such as acrylonitrile and 110-150 C. for tetranuoroethylene or ethylene. The olefine may be a polymer, e.g. natural rubber or polybutadiene. A large number of organo silicon compounds are referred to, conforming to the general formulµ and R x R<SP>1</SP> y X z Si-(in which the silicon atom is attached to one or more other silicon atoms), in which a is 1-4, b 0 to 3, c 0 to 3, x 1 to 3, y 0-2 and z 0 to 2. R is an alkyl radical of less than 5 carbon atoms, R<SP>1</SP> is any siliconbonded organic radical, free from aliphatic unsaturation, R<SP>11</SP> is any divalent hydrocarbon radical free from aliphatic unsaturation, and X is any hydrolysable or condensable group. A large number of olefinic compounds are referred to. In examples: (1) trifluorochloroethylene was reacted in the presence of,benzoyl peroxide in a rocker bomb at 110-150 C. with (a) 1000 c.s. viscosity trimethyl endblocked polydimethylsiloxane; (b) 10 c.s. viscosity trimethyl end-blocked polydimethylsiloxane; (c) a non-flowing polydimethylsiloxane; (d) (Me 2 SiO) 4 ; (e) (Me 3 Si) 2 O; (f) a 320 c.s. viscosity liquid of formula (Me 2 SiCH 2 ) x . The unreacted halogenated ethylene was recovered and the quantity reacted determined. The product from (a) was fractionated giving inter alia a liquid with good lubricating properties. The physical properties of the various fractions and the CF 2 =CFC1 to Si ratios are tabulated. Three of the fractions were further fractionated. (2) Divinylbenzene was reacted with a 1000 c.s. viscosity trimethyl endblocked polydimethylsiloxane. (3) As in (2) but using styrene, the product being fractionated. (4) As in (2) but using vinyl acetate, the product being fractionated. (5) As in (2) but using acrylonitrile, the product being fractionated. (6) A benzene-soluble non-flowing polydimethylsiloxane was reacted with acrylonitrile and the product fractionated. (7) Reacting the polysiloxane of Example (2) with 1-dodecene. (8) Reacting the polysiloxane of Example (2) with acrylamide and fractionating the product. (9) Reacting the polysiloxane of Example (2) with cis-dichloroethylene and fractionating the product. (10) Reacting the polysiloxane of Example (2) with hexafluorodichlorocyclopentene. (11) As in (8) but using (a) allyl alcohol; (b) allylamine, and (c) acrylic acid. (12) Reacting dimethyldiethoxysilane with trifluorochloroethylene, the product being more resistant to hydrolysis than the starting material. (13) Trifluorochloroethylene reacted with diethyldichlorosilane, tetramethylsilane and a resinous phenylmethylpolysilane. The Specification lists a large number of other starting materials including polymeric ethylenically unsaturated compounds such as natural rubber, polybutadiene, polychloroprene, butadienestyrene and butadiene-acrylonitrile copolymers and polyhexafluorobutadiene. The grafting of the olefin and the organosilicon compound may be carried out simultaneously with the polymerization of the olefin. Specification 688,166 is referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1131119XA | 1954-04-13 | 1954-04-13 | |
| US505561A US2958707A (en) | 1955-05-02 | 1955-05-02 | Diorganopolysiloxane-halogenated olefin graft copolymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB766528A true GB766528A (en) | 1957-01-23 |
Family
ID=90124762
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9286/55A Expired GB766528A (en) | 1954-04-13 | 1955-03-30 | A process for the production of organosilicon compounds |
| GB8518/56A Expired GB786142A (en) | 1954-04-13 | 1956-03-19 | A process for the production of organosilicon compounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8518/56A Expired GB786142A (en) | 1954-04-13 | 1956-03-19 | A process for the production of organosilicon compounds |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1131119A (en) |
| GB (2) | GB766528A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2909548A (en) * | 1956-03-27 | 1959-10-20 | Union Carbide Corp | Copolymers of mono-vinyl methyl siloxanes and chlorotrifluoroethylene |
| US3013915A (en) * | 1958-04-23 | 1961-12-19 | Owens Corning Fiberglass Corp | Reinforced polyolefins and process for making same |
| US3088964A (en) * | 1958-09-29 | 1963-05-07 | Dow Corning | 2-phenylpropyl organosiloxanes |
| US3139352A (en) * | 1962-08-08 | 1964-06-30 | Du Pont | Process of using a masking coating of a telomer of tetrafluoroethylene |
| JPS5113520B1 (en) * | 1966-12-01 | 1976-04-30 | ||
| US4412039A (en) | 1980-08-09 | 1983-10-25 | Bayer Aktiengesellschaft | Crosslinked silicone-vinyl polymer systems |
| GB2145423A (en) * | 1983-08-26 | 1985-03-27 | Gen Electric | Modified organopolysiloxane composition |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0684495B2 (en) * | 1986-06-03 | 1994-10-26 | 旭硝子株式会社 | Surface modifier |
-
1955
- 1955-03-30 GB GB9286/55A patent/GB766528A/en not_active Expired
- 1955-04-12 FR FR1131119D patent/FR1131119A/en not_active Expired
-
1956
- 1956-03-19 GB GB8518/56A patent/GB786142A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2909548A (en) * | 1956-03-27 | 1959-10-20 | Union Carbide Corp | Copolymers of mono-vinyl methyl siloxanes and chlorotrifluoroethylene |
| US3013915A (en) * | 1958-04-23 | 1961-12-19 | Owens Corning Fiberglass Corp | Reinforced polyolefins and process for making same |
| US3088964A (en) * | 1958-09-29 | 1963-05-07 | Dow Corning | 2-phenylpropyl organosiloxanes |
| US3139352A (en) * | 1962-08-08 | 1964-06-30 | Du Pont | Process of using a masking coating of a telomer of tetrafluoroethylene |
| JPS5113520B1 (en) * | 1966-12-01 | 1976-04-30 | ||
| US4412039A (en) | 1980-08-09 | 1983-10-25 | Bayer Aktiengesellschaft | Crosslinked silicone-vinyl polymer systems |
| GB2145423A (en) * | 1983-08-26 | 1985-03-27 | Gen Electric | Modified organopolysiloxane composition |
Also Published As
| Publication number | Publication date |
|---|---|
| GB786142A (en) | 1957-11-13 |
| FR1131119A (en) | 1957-02-18 |
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