GB603076A - Improvements in organo-siloxanes and methods of making them - Google Patents
Improvements in organo-siloxanes and methods of making themInfo
- Publication number
- GB603076A GB603076A GB3638/44A GB363844A GB603076A GB 603076 A GB603076 A GB 603076A GB 3638/44 A GB3638/44 A GB 3638/44A GB 363844 A GB363844 A GB 363844A GB 603076 A GB603076 A GB 603076A
- Authority
- GB
- United Kingdom
- Prior art keywords
- silicon
- treated
- phenyl
- aqueous
- water
- 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
- 125000005375 organosiloxane group Chemical group 0.000 title abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 16
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 abstract 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 15
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 abstract 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 14
- 239000000203 mixture Substances 0.000 abstract 14
- 239000005049 silicon tetrachloride Substances 0.000 abstract 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 8
- 229910052710 silicon Inorganic materials 0.000 abstract 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 6
- 229960000583 acetic acid Drugs 0.000 abstract 6
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 abstract 6
- 230000007062 hydrolysis Effects 0.000 abstract 6
- 238000006460 hydrolysis reaction Methods 0.000 abstract 6
- 238000006116 polymerization reaction Methods 0.000 abstract 6
- 239000010703 silicon Substances 0.000 abstract 6
- 239000002904 solvent Substances 0.000 abstract 6
- 239000004215 Carbon black (E152) Substances 0.000 abstract 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 4
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 abstract 4
- VISWXCASEQDFSG-UHFFFAOYSA-N ethanolate methylsilicon(3+) Chemical compound [O-]CC.[O-]CC.[O-]CC.C[Si+3] VISWXCASEQDFSG-UHFFFAOYSA-N 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- 229930195733 hydrocarbon Natural products 0.000 abstract 4
- 239000007788 liquid Substances 0.000 abstract 4
- 125000001624 naphthyl group Chemical group 0.000 abstract 4
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 abstract 4
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 abstract 2
- SUVOUQDWGSSOIE-UHFFFAOYSA-N C1(=CC=CC=C1)[Si](Cl)(Cl)Cl.[Si](OCC)(O)(O)O Chemical compound C1(=CC=CC=C1)[Si](Cl)(Cl)Cl.[Si](OCC)(O)(O)O SUVOUQDWGSSOIE-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- HMDDXIMCDZRSNE-UHFFFAOYSA-N [C].[Si] Chemical compound [C].[Si] HMDDXIMCDZRSNE-UHFFFAOYSA-N 0.000 abstract 2
- BHOSGTNQJWDBJD-UHFFFAOYSA-N [O-]CC.C1(=CC=CC=C1)[Si+](C)C Chemical compound [O-]CC.C1(=CC=CC=C1)[Si+](C)C BHOSGTNQJWDBJD-UHFFFAOYSA-N 0.000 abstract 2
- MMUMEHQPEMRODI-UHFFFAOYSA-N [O-]CC.C[Si+](C)C Chemical compound [O-]CC.C[Si+](C)C MMUMEHQPEMRODI-UHFFFAOYSA-N 0.000 abstract 2
- MIBFFZCLAQZZGL-UHFFFAOYSA-N [O-]CC.[O-]CC.C1(=CC=CC=C1)C[Si+2] Chemical compound [O-]CC.[O-]CC.C1(=CC=CC=C1)C[Si+2] MIBFFZCLAQZZGL-UHFFFAOYSA-N 0.000 abstract 2
- XNSDEMACCLVPPQ-UHFFFAOYSA-N [O-]CC.[O-]CC.C1(=CC=CC=C1)[Si+2]C Chemical compound [O-]CC.[O-]CC.C1(=CC=CC=C1)[Si+2]C XNSDEMACCLVPPQ-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- -1 anthracyl Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- IMFKTXPBWZHIJQ-UHFFFAOYSA-N benzyl(dichloro)silicon Chemical compound Cl[Si](Cl)CC1=CC=CC=C1 IMFKTXPBWZHIJQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- KWYZNESIGBQHJK-UHFFFAOYSA-N chloro-dimethyl-phenylsilane Chemical compound C[Si](C)(Cl)C1=CC=CC=C1 KWYZNESIGBQHJK-UHFFFAOYSA-N 0.000 abstract 2
- 238000000576 coating method Methods 0.000 abstract 2
- TYUACSACOUPEAG-UHFFFAOYSA-N dichloro(2-phenylethyl)silicon Chemical compound Cl[Si](Cl)CCC1=CC=CC=C1 TYUACSACOUPEAG-UHFFFAOYSA-N 0.000 abstract 2
- BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 abstract 2
- QFHGBZXWBRWAQV-UHFFFAOYSA-N dichloro-ethyl-phenylsilane Chemical compound CC[Si](Cl)(Cl)C1=CC=CC=C1 QFHGBZXWBRWAQV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000532 dioxanyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 239000012362 glacial acetic acid Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000000206 moulding compound Substances 0.000 abstract 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 230000001105 regulatory effect Effects 0.000 abstract 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 229920001187 thermosetting polymer Polymers 0.000 abstract 2
- 125000003944 tolyl group Chemical group 0.000 abstract 2
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 abstract 2
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 abstract 2
- 239000002966 varnish Substances 0.000 abstract 2
- 125000005023 xylyl group Chemical group 0.000 abstract 2
- 239000002253 acid 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
- C08G77/06—Preparatory processes
Abstract
Organo-siloxane compositions are made by mixing silicon tetrachloride or a tetra-alkoxy silicon with at least one mono-silane having from one to three monovalent hydrocarbon radicals which need not be the same, but which are selected from the group of alkyl, aryl and alkaryl radicals, attached to each silicon atom through carbon-silicon linkages, the remaining valencies of the silicon atoms being satisfied by chlorine or ethoxy radicals, hydrolysing the mixture by the gradual addition of water and if necessary heating the hydrolysis product. In the hydrolysis of the above mixture it is preferred to add the water dissolved in from one to four volumes of a common solvent such as alcohol, dioxane, acetic acid or acetone. Hydrocarbon radicals mentioned as suitable substituents for the mono-silanes referred to above include methyl and ethyl, propyl, butyl, isobutyl, amyl, hexyl, heptyl to octadecyl, phenyl, tolyl, xylyl, mesityl, mono-, di- and tri-ethyl and propyl phenyls, naphthyl, mono-and poly-naphthyls and anthracyl. If the mixture contains halogens, the preferred solvent is dioxane. After removal of the solvent and excess of water, the hydrolysis products are viscous water - immiscible liquids which are capable of further polymerization by heating. The amount of further polymerization is regulated by the use to which the products are to be put. In examples: (1) silicon tetrachloride and phenyl triethoxy silane are treated dropwise with aqueous alcohol; (2) silicon tetrachloride and diethyl silicon dichloride is treated with dry alcohol and the ester so formed hydrolysed with aqueous alcohol; (3) moist air is passed through a solution of silicon tetrachloride and diphenyl silicon dichloride for 18 hours; (4) silicon tetrachloride and diphenyl silicon dichloride is treated first with dry methyl alcohol and then with aqueous acetone; (5), (6) and (7) tetra-ethoxysilicon and dimethyl silicon diethoxide are treated with aqueous hydrochloric acid; (8) tetra-ethoxy silicon and phenyl methyl silicon di-ethoxide are warmed with alcoholic HCl and then diluted with aqueous HCl; (9) silicon tetrachloride and phenyl di-methyl silicon chloride is treated with dioxane and then with aqueous acetic acid; (10) tetra-ethoxy silicon and phenyl dimethyl silicon ethoxide is treated with aqueous alcohol containing a trace of HCl followed by excess of water; (11) tetra-ethoxy silicon and trimethyl silicon ethoxide is treated with aqueous alcohol; (12) tetra-ethoxy silicon methyl silicon tri-ethoxide and dimethyl silicon diethoxide are treated with aqueous alcohol; (13) equi-molecular proportions of ethyl orthosilicate phenyl silicon trichloride and phenylmethyl silicon dichloride are treated with aqueous dioxane; (14) a mixture of phenyl silicon trichloride, dimethyl silicon diethoxide, methyl silicon tri-ethoxide and ethyl orthosilicate in the molar ratio of 4 : 2 : 1 : 1 is treated with aqueous alcohol, and the product heated for one hour at 250 DEG C.; (15) silicon tetrachloride, ethyl silicon trichloride and phenyl ethyl silicon dichloride in the molar ratio 1 : 3 : 2.25 are treated in ether and glacial acetic acid solution with water and heated to 250 DEG C.; (16) a mixture of phenylmethyl silicon diethoxide, methyl silicon triethoxide and ethyl orthosilicate in the molar ratio 2 : 1 : 1 is treated with twice the theoretical amount of water at 60-80 DEG C. in the presence of a small amount of hydrochloric acid; (17) phenylethyl silicon dichloride, ethyl orthosilicate and ethyl silicon trichloride are treated in alcohol-ether solution with water and the product heated to 80 DEG to 300 DEG C. The properties of the products of the invention can be adjusted by varying the oxygen to silicon ratio. When this ratio is between 0.5 and 1.0, the products remain liquid with little tendency to polymerization, with a ratio greater than 1.0 the products form thermosetting compositions; the former class of materials are suitable for electrical filling media for transformers, circuit-breakers, cables and condensers, and the latter class for moulding compounds, film-forming coatings, varnishes and impregnating agents.ALSO:Organo-siloxane compositions are made by mixing silicon tetrachloride or a tetra-alkoxy silicon with at least one mono-silane having from one to three monovalent hydrocarbon radicals which need not be the same, but which are selected from the group of alkyl, aryl, and alkaryl radicals attached to each silicon atom through carbon-silicon linkages, the remaining valencies of the silicon atoms being satisfied by chlorine or ethoxy radicals, hydrolysing the mixture by the gradual addition of water and, if necessary, heating the hydrolysis product. In the hydrolysis of the above mixture, it is preferred to add the water dissolved in from one to four volumes of a common solvent such as alcohol dioxane, acetic acid or acetone. Hydrocarbon radicals mentioned as suitable substituents for the mono-silanes referred to above include methyl and ethyl, propyl, butyl, isobutyl, amyl, hexyl, heptyl to octadecyl, phenyl, tolyl, xylyl, mesityl, mono-, di- and tri-ethyl and propyl phenyls, naphthyl, mono-and poly-naphthyls and anthracyl. If the mixture contains halogens, the preferred solvent is dioxane. After removal of the solvent and excess of water, the hydrolysis products are viscous water-immiscible liquids which are capable of further polymerization by heating. The amount of further polymerization is regulated by the use to which the products are to be put. In examples: (1) silicon tetrachloride and phenyl triethoxy silane are treated dropwise with aqueous alcohol; (2) silicon tetrachloride and diethyl silicon dichloride is treated with dry alcohol and the ester so formed hydrolysed with aqueous alcohol; (3) moist air is passed through a solution of silicon tetrachloride and diphenyl silicon dichloride for 18 hours; (4) silicon tetrachloride and diphenyl silicon dichloride is treated first with dry methyl alcohol and then with aqueous acetone; (5), (6) and (7) tetra-ethoxysilicon and dimethyl silicon diethoxide are treated with aqueous hydrochloric acid; (8) tetra-ethoxy silicon and phenyl methyl silicon di-ethoxide were warmed with alcoholic HCl and then diluted with aqueous HCl acid; (9) silicon tetrachloride and phenyl di-methyl silicon chloride is treated with dioxane and then with aqueous acetic acid; (10) tetra-ethoxy silicon and phenyl dimethyl silicon ethoxide is treated with aqueous alcohol containing a trace of HCl followed by excess of water; (11) tetra-ethoxy silicon and trimethyl silicon ethoxide is treated with aqueous alcohol; (12) tetra-ethoxy silicon methyl silicon triethoxide, and dimethyl silicon diethoxide are treated with aqueous alcohol; (13) equimolecular proportions of ethyl orthosilicate phenyl silicon trichloride and phenylmethyl silicon dichloride are treated with aqueous dioxane; (14) a mixture of phenyl silicon trichloride, dimethyl silicon diethoxide, methyl silicon tri-ethoxide and ethyl orthosilicate in the molar ratio of 4 : 2 : 1 : 1 is treated with aqueous alcohol, and the product heated for one hour at 250 DEG C.; (15) silicon tetrachloride, ethyl silicon trichloride and phenyl ethyl silicon dichloride in the p molar ratio 1 : 3 : 2.25 are treated in ether and glacial acetic acid solution with water and heated to 250 DEG C.; (16) a mixture of phenylmethyl silicon diethoxide, methyl silicon triethoxide and ethyl orthosilicate in the molar ratio 2 : 1 : 1 is treated with twice the theoretical amount of water at 60-80 DEG C. in the presence of a small amount of hydrochloric acid; (17) phenylethyl silicon dichloride, ethyl orthosilicate, and ethyl silicon trichloride are treated in alcohol-ether solution with water and the product heated to 80 DEG to 300 DEG C. The properties of the products of the invention can be adjusted by varying the oxygen to silicon ratio. When this ratio is between 0.5 and 1.0, the products remain liquid with little tendency to polymerization, with a ratio greater than 1.0 the products form thermosetting composition. The former class of materials are suitable for electrical filling media for transformers, circuit-breakers, cables and condensers, and the latter class for moulding compounds, film-forming coatings, varnishes and impregnating agents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US603076XA | 1942-02-26 | 1942-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB603076A true GB603076A (en) | 1948-06-09 |
Family
ID=22028669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3638/44A Expired GB603076A (en) | 1942-02-26 | 1944-02-28 | Improvements in organo-siloxanes and methods of making them |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB603076A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4017528A (en) | 1973-11-16 | 1977-04-12 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Preparation of organically modified silicon dioxides |
| US4774310A (en) * | 1986-06-28 | 1988-09-27 | Dow Corning, Ltd. | Method for making siloxane resins |
-
1944
- 1944-02-28 GB GB3638/44A patent/GB603076A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4017528A (en) | 1973-11-16 | 1977-04-12 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Preparation of organically modified silicon dioxides |
| US4774310A (en) * | 1986-06-28 | 1988-09-27 | Dow Corning, Ltd. | Method for making siloxane resins |
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