DE803079C - Process for the production of silicon-containing polycondensation products - Google Patents
Process for the production of silicon-containing polycondensation productsInfo
- Publication number
- DE803079C DE803079C DEP3077A DEP0003077A DE803079C DE 803079 C DE803079 C DE 803079C DE P3077 A DEP3077 A DE P3077A DE P0003077 A DEP0003077 A DE P0003077A DE 803079 C DE803079 C DE 803079C
- Authority
- DE
- Germany
- Prior art keywords
- silicon
- polycondensation products
- production
- containing polycondensation
- weight
- 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
- 229910052710 silicon Inorganic materials 0.000 title claims description 8
- 239000010703 silicon Substances 0.000 title claims description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims description 5
- 238000006068 polycondensation reaction Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 4
- -1 silicon halide Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 3
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 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 description 4
- 239000005049 silicon tetrachloride Substances 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- 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
- C08G77/60—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 in which all the silicon atoms are connected by linkages other than oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
Description
Verfahren zur Herstellung siliciumhaltiger Polykondensationsprodukte ßs wurde gefunden, daß man siliciumhaltige Polykondensationsprodukte erhält, wenn man i'Mol eines Siliciumhalogenids, das etwa 2 an Silicium gebundene Halogenatome und Alkyl-, Aryl- oder Aralkylreste oder Oxyalkyl-, Oxyaryl- oder Oxyaralkylreste enthält, mit etwa 2 1101 eines Diols umsetzt, was unter Chlorwasserstoffabspaltung stattfindet, und anschließend mit Diisocyanaten behandelt. Die Umsetzungsgeschwindigkeit und die 1Tolekülgröße der entstehenden Polykondensationsprodukte hängen von der Temperatur ab. Es entstehen zähflüssige Produkte, die beim Erhitzen fest werden und sich z. 13. zur Herstellung von Vberzügen, Verklebungen und Formkörpern eignen.Process for the production of silicon-containing polycondensation products It has been found that silicon-containing polycondensation products are obtained if one mole of a silicon halide, which is about 2 halogen atoms bonded to silicon and alkyl, aryl or aralkyl radicals or oxyalkyl, oxyaryl or oxyaralkyl radicals contains, reacts with about 2 1101 of a diol, resulting in elimination of hydrogen chloride takes place, and then treated with diisocyanates. The speed of implementation and the 1 molecule size of the resulting polycondensation products depend on the Temperature. Viscous products are created that solidify when heated and z. 13. Suitable for the production of coatings, bonds and moldings.
Die als Ausgangsstoffe dienenden, durch Alkyl-oder Oxyalkylreste u. dgl. substituierten Siliciumhalogenide sind z. ß. durch Einwirkung der erforderlichen -Menge von Alkyl-, Aryl- oder Aralkylmagnesiumhalogeniden auf Siliciumtetrachlorid erhältlich. Dabei entstehen vorwiegend Derivate des Monosilans. Die durch Oxyalkyl-, Oxyaryl- oder Oxyaralkylreste substituierten Derivate kann man durch Einwirkung von Oxyverbindungen oder Alkylenoxyden auf Siliciumtetrachlorid herstellen.Serving as starting materials, by alkyl or oxyalkyl radicals u. Like. Substituted silicon halides are, for. ß. by acting the required - Amount of alkyl, aryl or aralkyl magnesium halides on silicon tetrachloride available. This mainly results in derivatives of monosilane. The oxyalkyl, Derivatives substituted by oxyaryl or oxyaralkyl radicals can be obtained by action of oxy compounds or alkylene oxides on silicon tetrachloride.
Geeignete Diole sind beispielsweise Ätliylenglykol, Butandiol oder Hexandiol. Man kann neben den Diolen auch geringe Mengen drei- oder noch höherwertiger Alkohole verwenden.Suitable diols are, for example, ethylene glycol, Butanediol or hexanediol. In addition to the diols, small amounts of trivalent or higher valent can also be used Use alcohols.
Als geeignete Diisocyanate seien Toluylendiisocyanat, Tetramethylendiisocyanat und Hexamethylendiisocyanat genannt.Suitable diisocyanates are tolylene diisocyanate and tetramethylene diisocyanate and called hexamethylene diisocyanate.
Beispiel1 256 Gewichtsteile eines Einwirkungsproduktes von 2 Mol Äthylenoxyd auf i Mol Siliciumtetrachlorid werden in 6oo Gewichtsteilen Chlorbenzol gelöst und bei etwa 5o° mit 124 Gewichtsteilen Äthylenglykol versetzt. Anschließend wird zum Austreiben des bei der Reaktion gebildeten Chlorwasserstoffs bis zum Sieden des Chlorbenzols erhitzt. Dann werden in die siedende Lösung langsam i68 Gewichtsteile Hexamethylendiisocyanat eingetragen. Die Lösung wird zunehmend viskoser. Je nach dem gewünschten Kondensationsgrad wird 1%2 bis 5 Stunden gekocht und anschließend das Chlorbenzol abdestilliert. Es entstehen feste zähe Massen, die durch Wärmeeinwirkung weiter kondensiert werden können. Die Produkte sind schmelz- und spritzbar und bis zu mittleren Polymerisationsgraden in organischen Lösungsmitteln löslich.Example 1 256 parts by weight of an action product of 2 moles of ethylene oxide on one mole of silicon tetrachloride are dissolved in 600 parts by weight of chlorobenzene and at about 5o ° mixed with 124 parts by weight of ethylene glycol. Then the Driving off the hydrogen chloride formed in the reaction until the boiling point Chlorobenzene heated. Then 168 parts by weight are slowly added to the boiling solution Hexamethylene diisocyanate entered. The solution becomes increasingly viscous. Depending on the desired degree of condensation 1% is boiled for 2 to 5 hours and then the chlorobenzene is distilled off. Solid viscous masses are created by the action of heat can be further condensed. The products are meltable and sprayable and up to soluble in organic solvents to medium degrees of polymerisation.
Beispie12 24o GPwichsteile eines durch Grignardsche ,Reaktion erhaltenen Einwirkungsproduktes von 1,7 Mol Brombenzol und Magnesium auf i Mol Siliciumtetrachlorid werden in 8oo Gewichtstölen Chlorbenzol gelöst und bei etwa 5o° mit 256 Gewichtsteilen Hexandiol-i,6 versetzt. Anschließend wird verfahren wie im vorstehenden Beispiel beschrieben. Die auskondensierten Produkte sind schmelz-, spritz- und spinnbar.Example: 24o parts of weight of one obtained by Grignard's reaction Action product of 1.7 moles of bromobenzene and magnesium on 1 mole of silicon tetrachloride are dissolved in 8oo parts by weight of chlorobenzene and at about 50 ° with 256 parts by weight Hexanediol-i, 6 added. Then proceed as in the previous example described. The condensed products can be melted, sprayed and spun.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR803079X | 1946-12-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE803079C true DE803079C (en) | 1951-02-26 |
Family
ID=9249929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP3077A Expired DE803079C (en) | 1946-12-11 | 1948-10-02 | Process for the production of silicon-containing polycondensation products |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE803079C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1011624B (en) * | 1953-01-08 | 1957-07-04 | Siemens Ag | Process for the production of hardenable, silicon-containing synthetic resins |
| DE1019725B (en) * | 1953-01-08 | 1957-11-21 | Siemens Ag | Electrical engineering insulating material |
| DE1021443B (en) * | 1953-01-08 | 1957-12-27 | Siemens Ag | High temperature resistant electrical insulating material |
| DE1115013B (en) * | 1958-06-02 | 1961-10-12 | Dow Corning A G | Process for the production of polyadducts from organopolysiloxanes and isocyanates with shaping |
-
1948
- 1948-10-02 DE DEP3077A patent/DE803079C/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1011624B (en) * | 1953-01-08 | 1957-07-04 | Siemens Ag | Process for the production of hardenable, silicon-containing synthetic resins |
| DE1019725B (en) * | 1953-01-08 | 1957-11-21 | Siemens Ag | Electrical engineering insulating material |
| DE1021443B (en) * | 1953-01-08 | 1957-12-27 | Siemens Ag | High temperature resistant electrical insulating material |
| DE1115013B (en) * | 1958-06-02 | 1961-10-12 | Dow Corning A G | Process for the production of polyadducts from organopolysiloxanes and isocyanates with shaping |
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