Cage octapoly(ethynyl dimethylsiloxy)silsesquioxane and its synthesis method

A technology of ethynyl dimethylsiloxane and ethynyl dimethyl chlorosilane is applied in the field of cage-type octapolysilsesquioxane and its synthesis, which can solve the problems of less terminal alkynyl POSS and the like, and achieve high reactivity , good development and application prospects, the effect of excellent high temperature resistance

Active Publication Date: 2018-02-09
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few studies on terminal alkynyl POSS. Weian Zhang et al. prepared single-terminal alkynyl POSS, and used its terminal alkynyl group, combined with ATPR and click chemistry to prepare mono-, di- and penta-telechelic polyphenylene containing POSS. Ethylene [Weian Zhang, Axel H.E.Muller, A "Click Chemistry" Approach to Linear and Star-Shaped Telechelic POSS-Containing Hybrid Polymers, Macromolecules, 2010, 43, 3148-3152]

Method used

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  • Cage octapoly(ethynyl dimethylsiloxy)silsesquioxane and its synthesis method
  • Cage octapoly(ethynyl dimethylsiloxy)silsesquioxane and its synthesis method
  • Cage octapoly(ethynyl dimethylsiloxy)silsesquioxane and its synthesis method

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Experimental program
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Embodiment 1

[0058] Synthesis of Cage Octa(ethynyldimethylsiloxy)silsesquioxane

[0059] 1). Synthesis of 1,3-diethynyl-1,1,3,3-tetramethyldisiloxane

[0060] 20ml of 1,3-dichloro-1,1,3,3-tetramethyldisiloxane, 100ml of acetone, 400ml of ethynylmagnesium chloride in 0.5M THF and Cu(PPh 3 ) 3 Add 0.11 g of Br into a 500 ml four-necked round-bottomed flask equipped with a condenser, protect it with nitrogen gas, stir it with magnetic force, heat the reactant to 55° C., and react at constant temperature for 8 hours. The solution was concentrated to about 50ml, and a large amount of precipitate was formed, which was washed with n-pentane and filtered. The filtrate was distilled under reduced pressure to obtain 1,3-diethynyl-1,1,3,3-tetramethyldisiloxane as a colorless transparent liquid with a yield of 46% and a purity of 97.7%. 1 H NMR (400MHz, CDCl 3 ): δ0.3(m, 6H, -CH 3 ), 2.4 (m, H, ≡CH).

[0061] 2).Synthesis of ethynyldimethylchlorosilane

[0062] Add 3.01 g of 1,3-diethynyl-1,1,3...

Embodiment 2

[0068] Synthesis of Cage Octa(ethynyldimethylsiloxy)silsesquioxane

[0069] 1). Synthesis of 1,3-diethynyl-1,1,3,3-tetramethyldisiloxane

[0070] 20ml of 1,3-dichloro-1,1,3,3-tetramethyldisiloxane, 100ml of toluene, 400ml of ethynylmagnesium chloride in 0.5M THF and Cu(PPh 3 ) 3 Add 0.22 g of Br into a 500 ml four-necked round-bottomed flask equipped with a condenser, protect it with nitrogen, and stir it magnetically. The reactant is heated to 80° C. and reacted at a constant temperature for 1 h. The solution was concentrated to about 50ml, and a large amount of precipitate was formed, which was washed with n-pentane and filtered. The filtrate was distilled under reduced pressure to obtain 1,3-diethynyl-1,1,3,3-tetramethyldisiloxane as a colorless and transparent liquid product with a yield of 48% and a purity of 97.4%. 1 H NMR (400MHz, CDCl 3 ): δ0.3(m, 6H, -CH 3 ), 2.4 (m, H, ≡CH).

[0071] 2).Synthesis of ethynyldimethylchlorosilane

[0072] Add 3.01 g of 1,3-diethy...

Embodiment 3

[0076] Synthesis of Cage Octa(ethynyldimethylsiloxy)silsesquioxane

[0077] 1). Synthesis of 1,3-diethynyl-1,1,3,3-tetramethyldisiloxane

[0078] 20ml of 1,3-dichloro-1,1,3,3-tetramethyldisiloxane, 100ml of DMF, 400ml of ethynylmagnesium chloride in 0.5M THF and Cu(PPh 3 ) 3 Add 0.33 g of Br into a 500 ml four-necked round-bottomed flask equipped with a condenser, protect it with nitrogen, and stir it magnetically. Heat the reactant to 100°C and react at a constant temperature for 1 h. The solution was concentrated to about 50ml, and a large amount of precipitate was formed, which was washed with n-pentane and filtered. The filtrate was distilled under reduced pressure to obtain 1,3-diethynyl-1,1,3,3-tetramethyldisiloxane as a colorless transparent liquid with a yield of 56% and a purity of 97.6%. FTIR (KBr, cm -1 ): 1098 (Si-O-Si), 1259 (Si-C), 2957 (≡CH); 1 H NMR (400MHz, CDCl 3 ): δ0.3(m, 6H, -CH 3), 2.4 (m, H, ≡CH).

[0079] 2).Synthesis of ethynyldimethylchlorosil...

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Abstract

The invention relates to a synthetic method of octakis (acetylenyl dimethyl siloxane) polysilsesquioxane. The synthetic method comprises the steps that (1) 1,3-acetylene-1,1,3,3-tetramethyldisiloxane is synthesized by Grignard reaction; (2) 1,3-acetylene-1,1,3,3-tetramethyldisiloxane is hydrolyzed to obtain ethinyl dimethyl silicon alcohol, and a chloridizing agent is used for chloridizing silicon hydroxyl to obtain acetenyl dimethylchlorosilane; (3) tetraethoxysilane is used, hydrolytic condensation is performed under an alkaline condition provided by tetramethylammonium hydroxide, and octamer tetramethylammonium silicate is obtained; (4) the octamer tetramethylammonium silicate and the acetenyl dimethylchlorosilane react to obtain the octakis (acetylenyl dimethyl siloxane) polysilsesquioxane. The prepared octakis (acetylenyl dimethyl siloxane) polysilsesquioxane has end alkynyl and excellent high temperature resistance and high reactivity, and can be used for preparing nanometer POSS (polyhedral oligomeric silsesquioxane) materials; the octakis(acetylenyl dimethyl siloxane)polysilsesquioxane can be applied in spatial and medical functional materials and the like and has an excellent development and application prospect.

Description

【Technical field】 [0001] The invention relates to the technical field of material chemistry, in particular to a cage octapoly(ethynyl dimethylsiloxy)silsesquioxane and a synthesis method thereof. 【Background technique】 [0002] Polyhedral oligomeric silsesquioxane (Polyhedral oligomeric silsesquioxane, hereinafter referred to as POSS) is a kind of organosilicon compound with special molecular structure. groups or active functional groups. Due to the special structure of POSS, adding it to the polymer system can significantly improve the thermal properties, mechanical properties and biocompatibility of organic polymers [Zhang Lipei. Synthesis and analysis of functionalized cage silsesquioxane (POSS) Characterization and properties of epoxy resin composites [D]. Beijing, Beijing University of Chemical Technology, 2004.]. Using inactive POSS, the performance of POSS-based polymer materials obtained by physical blending method is unstable and prone to phase separation; while u...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/21
CPCC07F7/21
Inventor 黄发荣步晓君周燕闫德强
Owner EAST CHINA UNIV OF SCI & TECH
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