DE834990C - Process for the preparation of ethyleneimine compounds of silicon - Google Patents
Process for the preparation of ethyleneimine compounds of siliconInfo
- Publication number
- DE834990C DE834990C DEP13866D DEP0013866D DE834990C DE 834990 C DE834990 C DE 834990C DE P13866 D DEP13866 D DE P13866D DE P0013866 D DEP0013866 D DE P0013866D DE 834990 C DE834990 C DE 834990C
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- ethyleneimine
- benzene
- silicon
- 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
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 3
- 229910052710 silicon Inorganic materials 0.000 title claims description 3
- 239000010703 silicon Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000005046 Chlorosilane Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- -1 tributoxyethyleneiminosilane Chemical class 0.000 description 4
- PJMZOZSTBHYHFW-UHFFFAOYSA-N dibenzyl(dichloro)silane Chemical compound C=1C=CC=CC=1C[Si](Cl)(Cl)CC1=CC=CC=C1 PJMZOZSTBHYHFW-UHFFFAOYSA-N 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QEHKWLKYFXJVLL-UHFFFAOYSA-N dichloro(dimethoxy)silane Chemical compound CO[Si](Cl)(Cl)OC QEHKWLKYFXJVLL-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- LWZNVSGTKHWYAU-UHFFFAOYSA-N bis(aziridin-1-yl)-dimethylsilane Chemical compound C1CN1[Si](C)(C)N1CC1 LWZNVSGTKHWYAU-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- CBVJWBYNOWIOFJ-UHFFFAOYSA-N chloro(trimethoxy)silane Chemical compound CO[Si](Cl)(OC)OC CBVJWBYNOWIOFJ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HRYDYCUCHYGDBK-UHFFFAOYSA-N dibutoxy(dichloro)silane Chemical compound CCCCO[Si](Cl)(Cl)OCCCC HRYDYCUCHYGDBK-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- SVHQXUKYPYRNEC-UHFFFAOYSA-N n-ethyl-n-trichlorosilylethanamine Chemical compound CCN(CC)[Si](Cl)(Cl)Cl SVHQXUKYPYRNEC-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- RYFIHIMBHQWVNQ-UHFFFAOYSA-N tributoxy(chloro)silane Chemical compound CCCCO[Si](Cl)(OCCCC)OCCCC RYFIHIMBHQWVNQ-UHFFFAOYSA-N 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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
- D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
Description
Verfahren zur Herstellung von Äthyleniminverbindungen des Siliciums Es wurde gefunden, daß man Äthyleniminverbindungen der allgemeinen Formel worin die Wasserstoffatome des Äthyleniminringes durch Alkylreste ersetzt sein können und worin n die Zahlen 3, 2 oder Z bedeutet und R für einen, zwei oder drei gleiche oder verschiedene organische Reste, mit Ausnahme von a, ß-Alkyleniminresten steht, erhält, wenn man die entsprechenden Chlorsilane mit Äthylenimin oder anderen a, ß-Alkyleniminen umsetzt. Man arbeitet in Gegenwart säurebindender Mittel, z. B. tertiärer Amine, Pyridin, Ammoniak, Natrium- oder Kaliumcarbonat. Die Umsetzung erfolgt zweckmäßig in einem indifferenten organischen Lösungsmittel.Process for the preparation of ethyleneimine compounds of silicon It has been found that one can use ethyleneimine compounds of the general formula in which the hydrogen atoms of the ethyleneimine ring can be replaced by alkyl radicals and in which n is the numbers 3, 2 or Z and R stands for one, two or three identical or different organic radicals, with the exception of a, ß-alkylenimine radicals, if the corresponding chlorosilanes with ethylene imine or other a, ß-alkylene imines. You work in the presence of acid-binding agents, for. B. tertiary amines, pyridine, ammonia, sodium or potassium carbonate. The reaction is expediently carried out in an inert organic solvent.
Diese neuen Verbindungen stellen wertvolle Produkte dar, die zur Veredlung von Textilien und in der Kunststoffindustrie Verwendung finden sollen.These new compounds represent valuable products that can be refined of textiles and in the plastics industry should be used.
Beispiele Z. Zu einer Lösung von 25 Gewichtsteilen Äthylenimin und 75 Gewichtsteilen Triäthylamin in 500 Gewichtsteilen trockenem Benzol läßt man unter Eiskühlung langsam eine Lösung von 142 Gewichtsteilen Tributoxychlorsilan in Zoo Gewichtsteilen Benzol eintropfen. Nach Beendigung des Zutropfens erhöht man die Temperatur langsam auf 2o bis 25°, rührt eine Stunde nach und saugt das ausgeschiedene Triäthylaminchlorhydrat ab. -Die Benzollösung wird fraktioniert destilliert, und man erhält in guter Ausbeute Tributoxyäthyleniminosilan vom Siedepunkt ioo° bei i mm Quecksilber als farblose Flüssigkeit.Examples Z. A solution of 142 parts by weight of tributoxychlorosilane in zoo parts by weight of benzene is slowly added dropwise to a solution of 25 parts by weight of ethyleneimine and 75 parts by weight of triethylamine in 500 parts by weight of dry benzene. After the dropwise addition, the temperature is slowly increased to 20 to 25 °, the mixture is stirred for one hour and the triethylamine chlorohydrate which has precipitated is filtered off with suction. The benzene solution is fractionally distilled, and tributoxyethyleneiminosilane is obtained in good yield with a boiling point of 100 ° at 1 mm of mercury as a colorless liquid.
2. Zu einer Lösung von 51 Gewichtsteilen Äthylenimin und 12o Gewichtsteilen Triäthylamin in 6oo Gewichtsteilen trockenem Benzol läßt man bei 5 bis io° 122 Gewichtsteile Dibutoxydichlorsilan in ioo Gewichtsteilen Benzol eintropfen. Die Aufarbeitung erfolgt gemäß Beispiel i. Man erhält Dibutoxydiäthyleniminosilan als farblose Flüssigkeit, Kpa 93 bis 94°.2. To a solution of 51 parts by weight of ethyleneimine and 12o parts by weight Triethylamine in 600 parts by weight of dry benzene is left at 5 to 10 ° 122 parts by weight Drip in dibutoxydichlorosilane in 100 parts by weight of benzene. The work-up takes place according to example i. Dibutoxydiethyleniminosilane is obtained as a colorless liquid, Kpa 93 to 94 °.
3. Zu einer Lösung von 36 Gewichtsteilen Äthylenimin und 9o Gewichtsteilen Triäthylamin in 6oo Gewichtsteilen trockenem Benzol läßt man bei io bis 15° 42 Gewichtsteile Diäthylaminotrichlorsilan in 5o Gewichtsteilen Benzol eintropfen. Nach Aufarbeitung gemäß Beispiel i erhält man Diäthylaminotriäthyleniminosilan als farblose Flüssigkeit, Kplo ioo°.3. To a solution of 36 parts by weight of ethyleneimine and 90 parts by weight Triethylamine in 600 parts by weight of dry benzene is left at 10 to 15 ° 42 parts by weight Drop in diethylaminotrichlorosilane in 50 parts by weight of benzene. After work-up according to example i, diethylaminotriäthyleniminosilan is obtained as a colorless liquid, Kplo ioo °.
4. Zu einer Lösung von 24 Gewichtsteilen Äthylenimin und 54 Gewichtsteilen Triäthylamin in 3oo Gewichtsteilen Benzol läßt man bei o bis 1o° 4o Gewichtsteile Dimethoxydichlorsilan (Kp. 99 bis ioo°) in 200 Gewichtsteilen Benzol unter Rühren eintropfen. 'Ulan läßt mehrere Stunden nachrühren, saugt vom Triäthylaminchlorhydrat ab, destilliert das Benzol im schwachen Vakuum ab und erhält als Rückstand Dimethoxydiäthyleniminosilan als farblose Flüssigkeit vom Kpli 49 bis 50°.4. To a solution of 24 parts by weight of ethyleneimine and 54 parts by weight Triethylamine in 300 parts by weight of benzene is left at 0 to 10 ° 40 parts by weight Dimethoxydichlorosilane (bp 99 to 100 °) in 200 parts by weight of benzene with stirring a drop. 'Ulan can be stirred for several hours, sucks in the triethylamine chlorohydrate off, the benzene is distilled off in a weak vacuum and the residue is dimethoxydiethyleniminosilane as a colorless liquid from Kpli 49 to 50 °.
An Stelle von Dimethoxydichlorsilan kann Trimethoxychlorsilan (Kp. iio bis 112°) in ähnlicher Weise eingesetzt werden.Instead of dimethoxydichlorosilane, trimethoxychlorosilane (Kp. iio to 112 °) can be used in a similar way.
5. Zu einer Lösung von 18 Gewichtsteilen Äthylenimin und 24 Gewichtsteilen Triäthylamin in 25o Gewichtsteilen trockenem Benzol läßt man bei 5 bis io° 25,8 Gewichtsteile Dimethyldichlorsilan in ioo Gewichtsteilen Benzol eintropfen. Sodann steigert man die Temperatur auf 2o bis 25° und rührt noch 2 Stunden nach. Man saugt nun vom ausgeschiedenen Triäthylaminchlorhydrat ab und erhält nach Abdestillieren des Benzols im Vakuum Dimethyldiäthyleniminosilan als farblose Flüssigkeit. 6. Zu einer Lösung von io Gewichtsteilen Äthylenimin und 25 Gewichtsteilen Triäthylamin in i5o Gewichtsteilen trockenem Benzol läßt man bei 5 bis io° 28,1 Gewichtsteile Dibenzyldichlorsilan in i5o Gewichtsteilen trockenem Benzol eintropfen. 5. 25.8 parts by weight of dimethyldichlorosilane in 100 parts by weight of benzene are added dropwise to a solution of 18 parts by weight of ethyleneimine and 24 parts by weight of triethylamine in 250 parts by weight of dry benzene. The temperature is then increased to 20 to 25 ° and the mixture is stirred for a further 2 hours. The triethylamine chlorohydrate which has separated out is then suctioned off and, after the benzene has been distilled off in vacuo, dimethyldiethyleniminosilane is obtained as a colorless liquid. 6. 28.1 parts by weight of dibenzyldichlorosilane in 150 parts by weight of dry benzene are added dropwise to a solution of 10 parts by weight of ethyleneimine and 25 parts by weight of triethylamine in 150 parts by weight of dry benzene.
Nach dem Aufarbeiten gemäß Beispiel i erhält man Dibenzyldiäthyleniminosilan, Kpo,5 168 bis 17o°.After working up according to Example i, dibenzyldiethyleniminosilane is obtained, Kpo, 5 168 to 17o °.
7. Zu einer Aufschlämmung von io Gewichtsteilen Äthylenimin, 35 Gewichtsteilen wasserfreiem Kaliumcarbonat und 13o Gewichtsteilen trockenem Essigester läßt man 28,1 Gewichtsteile Dibenzyldichlorsilan in 5o Gewichtsteilen Essigester bei o° eintropfen. Man erhält nach dem Aufarbeiten gemäß Beispiel i Dibenzyldiäthyleniminosilan (vgl. Beispiel 6).7. To a slurry of 10 parts by weight of ethylene imine, 35 parts by weight anhydrous potassium carbonate and 130 parts by weight of dry ethyl acetate are left 28.1 parts by weight of dibenzyldichlorosilane in 50 parts by weight of ethyl acetate at 0 °. After working up according to Example i, dibenzyldiethyleniminosilane (cf. Example 6).
B. Zu einer Lösung von 14 Gewichtsteilen C-Methyläthylenimin und 25 Gewichtsteilen Triäthylamin in i5o Gewichtsteilen Benzol läßt man bei o° 28,1 Gewichtsteile Dibenzyldichlorsilan in ioo Gewichtsteilen trockenem Benzol eintropfen. Nach dem Aufarbeiten gemäß Beispiel i erhält man Dibenzyldi-(C-methvläthylenimino)-silan vom KPD,, 173°.B. To a solution of 14 parts by weight of C-methylethyleneimine and 25 Parts by weight of triethylamine in 150 parts by weight of benzene are left at 28.1 parts by weight Drip in dibenzyldichlorosilane in 100 parts by weight of dry benzene. After this Working up according to Example i gives dibenzyldi- (C-methvläthylenimino) silane from KPD ,, 173 °.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP13866D DE834990C (en) | 1948-10-02 | 1948-10-02 | Process for the preparation of ethyleneimine compounds of silicon |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP13866D DE834990C (en) | 1948-10-02 | 1948-10-02 | Process for the preparation of ethyleneimine compounds of silicon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE834990C true DE834990C (en) | 1952-03-27 |
Family
ID=7364845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP13866D Expired DE834990C (en) | 1948-10-02 | 1948-10-02 | Process for the preparation of ethyleneimine compounds of silicon |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE834990C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3336157A (en) * | 1963-12-06 | 1967-08-15 | Nathaniel C Shane | Water and oil repellant finishes and methods of applying them |
| US3468818A (en) * | 1966-08-01 | 1969-09-23 | Nalco Chemical Co | Polymers and process of preparation |
-
1948
- 1948-10-02 DE DEP13866D patent/DE834990C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3336157A (en) * | 1963-12-06 | 1967-08-15 | Nathaniel C Shane | Water and oil repellant finishes and methods of applying them |
| US3468818A (en) * | 1966-08-01 | 1969-09-23 | Nalco Chemical Co | Polymers and process of preparation |
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