CN1421446A - Ethynylbenzene silane and its prepn - Google Patents
Ethynylbenzene silane and its prepn Download PDFInfo
- Publication number
- CN1421446A CN1421446A CN 02151140 CN02151140A CN1421446A CN 1421446 A CN1421446 A CN 1421446A CN 02151140 CN02151140 CN 02151140 CN 02151140 A CN02151140 A CN 02151140A CN 1421446 A CN1421446 A CN 1421446A
- Authority
- CN
- China
- Prior art keywords
- compound
- bond
- phenylacetylene
- aryl
- preparation
- 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.)
- Granted
Links
Abstract
The present invention discloses one kind of compound containing phenylethynyl and Si-H bond and its preparation. The compound is prepared with silane dichloride containing Si-H bond and phenylethyne as material and the reaction between phenylethyne and Grignard reagent to prepare organic magnesium compound and further reaction with silane dichloride containing Si-H bond. The compound may be polymerized or copolymerized with other organic silicide containing Si-H bond to prepare material with excellent heat resistance and has mass retention percentage, and the material may find its wide application in aeronautics and astronautics.
Description
Technical field:
The present invention relates to a kind of organosilane monomer and preparation method thereof.
Background technology
Organosilicon polymer is the speciality polymer material, has good performance.In recent years, in molecular chain, contain si-h bond simultaneously and carbon carbon triple-linked organosilicon polymer is constantly reported.These polymkeric substance produce crosslinking curing by the hydrosilylation addition reaction between carbon carbon triple bond and the si-h bond, thereby obtain having the material of good heat-resisting and ablation resistance.
Summary of the invention
The present invention has synthesized a kind of novel silane containing hydrogen that contains two aryl ethane bases from Molecular Structure Design.Because its intramolecularly contains two ethynyls and a si-h bond, so can form polymkeric substance by polyreaction.Simultaneously, owing to contain aryl ethane structure and Siliciumatom, its polymkeric substance thereby have good thermotolerance and ablation resistance has the potential purposes at aspects such as preparation high temperature resistant composite, ceramic forerunners.
Technical scheme:
Phenylacetylene substituted silane of the present invention has following structural formula:
Wherein: R is hydrogen, alkyl or aryl.
The key step for preparing phenylacetylene substituted silane of the present invention is:
With phenylacetylene and hydrogeneous dichlorosilane (RHSiCl
2) be that raw material, anhydrous tetrahydro furan (THF) they are solvent, by Grignard reagent (R
1MgX) make.Its reaction equation is as follows:
Wherein: R is hydrogen, alkyl or aryl, R
1Be alkyl or aryl, X is Cl or Br.
The mol ratio of phenylacetylene and hydrogeneous dichlorosilane is 2-2.2: 1;
Temperature of reaction is 60-70 ℃, and the reaction times is 4-8h.
Specific implementation method
The THF drips of solution that will contain monobromethane is added in the THF suspension of MAGNESIUM METAL, and the dropping time is 30～60 minutes, drips Bi Huiliu 1～2 hour; Be chilled to the THF solution that drips phenylacetylene after the room temperature, the dropping time is 30～60 minutes, drips Bi Huiliu 1～2 hour; Be chilled to the THF solution that drips the dichloro silane containing hydrogen after the room temperature again, the dropping time is 30～60 minutes, drips Bi Huiliu 1～2 hour.Add 1M hydrochloric acid and benzene after being chilled to room temperature, divide oil-yielding stratum, dry filter gets product after steaming desolventizes.Whole process of preparation is preferably under rare gas element (gas that chemical property is stable, as: nitrogen, helium or the argon gas etc.) protection carries out.
Phenylacetylene substituted silane of the present invention, by autohemagglutination or contain the poly-copolymerization of organosilicon of si-h bond with other and make and have good thermotolerance and ablation resistance material, it has a wide range of applications in fields such as Aeronautics and Astronautics.
Below by example is that the invention will be further described, but it does not limit protection scope of the present invention:
Embodiment
With 3.66g metal magnesium chips, granule iodine crystalline substance and 50ml THF add in the four-hole bottle.Drip the solution that is mixed with by 14.85g monobromethane and 50ml THF with constant pressure funnel, dropwise reflux 2h.After the reactant cooling, drip the solution that 13.2g phenylacetylene and 50ml THF are made into, dropwise reheat backflow 1h.After the cooling of question response thing, continue to drip the solution of 7.42g dimethyl dichlorosilane (DMCS) and 40ml THF, dropwise reflux 1h.More than each step all under the nitrogen protection condition, carry out.After the question response thing is chilled to room temperature then, in condition of ice bath downhill reaction bottle, drip the HCl of the 1mol/L of 120ml.After dropwising, in reactant, add 50ml benzene, collect upper strata oily matter, to wherein adding anhydrous Na
2SO
4Spend the night.Remove by filter siccative then, promptly get product after the filtrate decompression steaming is desolventized.
Structured data is as follows:
1H NMR (CDCl
3, 500MHz): δ=0.5 (3H, CH
3), 4.6 (1H, SiH), 7.4-7.6 (10H, C
6H
5),
1MS:m/e (%): m/e=246 (M, 246); IR (streak method) υ
Si-H=2100cm
-1
Claims (5)
1, a kind of phenylacetylene substituted silane is characterized in that, described compound has following structural formula:
Wherein: R is H, alkyl or aryl.
2, compound as claimed in claim 1 is characterized in that, wherein R is a methyl.
3, prepare the method for the described compound of claim 1, it is characterized in that, the key step of described method is with phenylacetylene and hydrogeneous dichlorosilane (RHSiCl
2) for raw material, anhydrous tetrahydro furan are solvent, by Grignard reagent (R
1MgX) make product,
Wherein: R is H, alkyl or aryl, R
1Be alkyl or aryl, X is Cl or Br
The mol ratio of phenylacetylene and hydrogeneous dichlorosilane is 2-2.2: 1;
Temperature of reaction is 60-70 ℃, and the reaction times is 4-8h.
4, preparation method as claimed in claim 3 is characterized in that, wherein said Grignard reagent is CH
3CH
2MgBr.
As claim 3 or 4 described preparation methods, it is characterized in that 5, whole process of preparation is carried out having under the inert gas conditions.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 02151140 CN1203078C (en) | 2002-12-06 | 2002-12-06 | Ethynylbenzene silane and its prepn |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 02151140 CN1203078C (en) | 2002-12-06 | 2002-12-06 | Ethynylbenzene silane and its prepn |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1421446A true CN1421446A (en) | 2003-06-04 |
| CN1203078C CN1203078C (en) | 2005-05-25 |
Family
ID=4751926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 02151140 Expired - Fee Related CN1203078C (en) | 2002-12-06 | 2002-12-06 | Ethynylbenzene silane and its prepn |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1203078C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100400571C (en) * | 2004-05-18 | 2008-07-09 | 华东理工大学 | High-temperature-resistance silicon-containing copolymer and its preparing method |
| CN102010510A (en) * | 2010-10-21 | 2011-04-13 | 华东理工大学 | Novel high-temperature resistant phenylacetylene terminated poly (acetenyl-silane) and preparation method thereof |
| CN101665506B (en) * | 2009-09-10 | 2012-01-04 | 华东理工大学 | Novel boron-and benzene-contained acetenyl oxosilane and preparation method thereof |
-
2002
- 2002-12-06 CN CN 02151140 patent/CN1203078C/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100400571C (en) * | 2004-05-18 | 2008-07-09 | 华东理工大学 | High-temperature-resistance silicon-containing copolymer and its preparing method |
| CN101665506B (en) * | 2009-09-10 | 2012-01-04 | 华东理工大学 | Novel boron-and benzene-contained acetenyl oxosilane and preparation method thereof |
| CN102010510A (en) * | 2010-10-21 | 2011-04-13 | 华东理工大学 | Novel high-temperature resistant phenylacetylene terminated poly (acetenyl-silane) and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1203078C (en) | 2005-05-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Iwahara et al. | Synthesis and properties of ethynylene-disilanylene copolymers | |
| JP2018027962A (en) | New cyclo disilazane derivative and method for manufacturing the same, and silicon containing thin film using cyclo disilazane derivative | |
| KR20150123766A (en) | Novel amino-silyl amine compound, method for manufacturing thereof and silicon-containing thin film use the same | |
| CN104591741A (en) | Method for preparing SiNCB ceramic material | |
| TW201605877A (en) | Monoaminosilane compounds | |
| CN104130417A (en) | High-temperature silicon alkyne resin containing nitrogen and preparation method thereof | |
| CN100564374C (en) | Organic compound with nucleocapsid structure | |
| CN1203078C (en) | Ethynylbenzene silane and its prepn | |
| CN102226000B (en) | Novel boron silicon alkyne hybrid high temperature resistant resin and preparation method thereof | |
| CN103524746B (en) | A kind of Borazine aryne resin and preparation method thereof | |
| CN104004194A (en) | Silicon alkyne hybrid high temperature-resistant resin and preparation method thereof | |
| CN101591438B (en) | Preparation method for liquid polycarbosilane precusor | |
| CN105542172A (en) | Boron-silicon-alkyne polymer containing carborane in main chain and preparation method of boron-silicon-alkyne polymer | |
| CN111333844B (en) | Preparation method of high-heat-resistance silicon oxide alkyne hybrid resin | |
| CN100506827C (en) | Diphenylacetylene silane novle synthesis method | |
| US5552505A (en) | High temperature copolymers from inorganic-organic hybrid polymers and multi-ethynylbenzenes | |
| CN112125931A (en) | Synthesis method of bis (tert-butylamine) bis (dimethylamine) tungsten (VI) | |
| JPH01129034A (en) | Polymer based on boron and nitrogen, its production and use thereof in ceramic product based on boron nitride and production thereof | |
| CN101139442B (en) | Organic-inorganic hybrid resin containing sesquialter siloxane and preparation method and use thereof | |
| CN102010510A (en) | Novel high-temperature resistant phenylacetylene terminated poly (acetenyl-silane) and preparation method thereof | |
| US4845255A (en) | Method of preparing cyclic disilanylene-acetylenes | |
| CN100506826C (en) | Triphenylacetylene silane novle synthesis method | |
| US5777051A (en) | Photoluminescent silacyclobutene monomers and polymers | |
| CN101585850A (en) | Aromatic cyanate ester monomer containing silicon and preparation method thereof | |
| CN101831077A (en) | Phenylo boric acid-silane-ethynyl polymer and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20050525 Termination date: 20151206 |
|
| EXPY | Termination of patent right or utility model |