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Clathrate sesquialter siloxane aryne resin containing octamethyl pyrophosphoramide and method for preparing the same

A technology of octamethylcage and siloxane aryne, which is applied in the direction of silicon organic compounds, can solve the problems of difficult formation of uniform structure materials, high raw material prices, long synthesis time, etc., and achieve high thermal decomposition residual rate and mechanical properties Excellent, easy-to-apply effect

Inactive Publication Date: 2008-04-02
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Domestic and international researches on polymers containing POSS mainly focus on the use of monofunctional or octafunctional POSS to prepare capped, side chain and star-shaped polymers (Joseph B.Carroll et al., Macromolecules 2003, 36, 6289-6291; Chyi-Ming Leu et al., Chem.Mater.2003, 15, 2261-2265; Junchao Huanget al., Polymer 2005, 46, 7018-7027), while POSS is introduced into the main chain, and the research on polymers with linear structures is compared Less, the main reason: it is difficult to synthesize difunctional POSS compounds, and the raw materials used in the functionalization reaction are mainly cyclopentyl and cyclohexyl POSS, the price of raw materials is high, the synthesis time is long, and the yield is low; POSS synthesizes a linear structure, which requires strict control of the reaction, and it is not easy to form a material with a uniform structure
However, foreign scholars have done some research on linear polymers containing POSS, and there are no relevant reports in China.

Method used

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  • Clathrate sesquialter siloxane aryne resin containing octamethyl pyrophosphoramide and method for preparing the same
  • Clathrate sesquialter siloxane aryne resin containing octamethyl pyrophosphoramide and method for preparing the same
  • Clathrate sesquialter siloxane aryne resin containing octamethyl pyrophosphoramide and method for preparing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Synthesis of compound (II) octamethyl clathrate silsesquioxane

[0032] Add 26.81 g (0.15 mol) of methyltriethoxysilane (MTES) and 78.18 g of absolute ethanol into a 250 ml four-neck flask equipped with stirring, a constant pressure funnel, a thermometer and a spherical condenser, and add them through the constant pressure funnel. 18.00 g (1.00 mol) of ionized water and 1.10 g (0.012 mol) of tetramethylammonium hydroxide were reacted at a constant temperature of 60°C for 40 hours to obtain a yellowish solid. Suction filtration, washing with water, and vacuum drying yielded 8.33 g of a white solid with a yield of 82.6%. solid 29 Si-NMR (99MHz, 25°C) δ: -65.97 (Si-CH 3 , S); FT-IR (KBr, 25°C) v=2971.4cm -1 (CH 3 ), v=1269.63cm -1 (Si-C), γ=1411.6cm -1 (CH 3 ), v=1113.1cm - 1 (Si-O-Si).

Embodiment 2

[0033] Example 2 Synthesis of compound (III) difluorooctamethyl clathrate silsesquioxane

[0034] Add 2.59g (4.83mmol) of compound (II) octamethyl clathrate silsesquioxane and 250ml CHCl in a 500ml four-neck flask equipped with stirring, constant pressure funnel, thermometer and spherical condenser 3 , under nitrogen protection, start stirring, 4.11g (28.98mmol) of boron trifluoride diethyl ether was added dropwise to the system from a constant pressure funnel, reflux at 70°C for 30h, and 10ml of deionized water was used to terminate the reaction. Liquid separation obtains organic phase, removes solvent, obtains yellowish solid, crosses column (SiO 2 , CH 2 Cl 2 ) purification, and then recrystallized in n-hexane solution to obtain 0.50 g of white product with a yield of 18.6%. 1 H-NMR (500MHz, CDCl 3 , 25°C) δ: 0.26 (J=4.18Hz, 6H, D), 0.19 (12H, S), 0.17 (6H, S); 29 Si-NMR (99MHz, CDCl 3 , 25°C) δ: -59.79 (J=252Hz, Si-F, D), -64.40 (Si-CH 3 , S), -64.98 (Si-CH 3 , ...

Embodiment 3

[0035] Example 3 Preparation of aryne resin containing octamethyl clathrate silsesquioxane (OMPOSS-DEB-1)

[0036] Add treated 1.94g (0.0807mol) magnesium powder and 20ml THF into a 250ml four-neck flask equipped with a stirring, constant pressure funnel and a spherical condenser. Under nitrogen protection, slowly drop 5.86g (0.0538mol) through the constant pressure funnel. ) mixed solution of bromoethane and 20ml THF, 1.5h was added dropwise, and refluxed for 1.5h to obtain gray-black ethyl Grignard reagent. A mixed solution of 4.51g (0.0358mol) of diethynylbenzene and 20ml of THF was added dropwise under cooling in an ice-water bath, the reaction mixture gradually changed from grayish black to white, and the dropwise addition was completed within 1.0h, and then refluxed for 2.0h. Under cooling in a water bath, a mixed solution of 10.00 g (0.0179 mol) of compound (III) difluorooctamethyl clathrate silsesquioxane and 100 ml of THF was slowly added through a constant pressur...

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Abstract

The present invention discloses an 8-methyl cage-shaped silsesquioxane resin with a structure as shown in the figure. The resin has the following characteristics: 1) the structure of the synthesized resin can be controlled; 2) the resin is solid at the room temperature; the softening point is low; the resin can be dissolved in a plurality of common solvents; and the application is convenient; 3) the resin can do the solidification reaction with the influence of heat, irradiation, or even light to form a highly cross-linked polymer; and no small molecules are released in the solidification process; 4) the solidified resin has good mechanical properties, excellent chemical resistance and high heat resistance or heat-resistant oxidation, that is, the high temperature of thermal decomposition and the residual rate of thermal decomposition; 5) the resin has good dielectric properties and thermal insulation properties after solidification; 6) the resin can do the ceramic reaction; 7) the resin and the fiber have good bonding performances. The mechanical properties of composite material are good.

Description

technical field [0001] The invention relates to a resin in the field of organic synthesis, in particular to an octamethyl clathrate silsesquioxane aryne resin and a preparation method thereof. Background technique [0002] Cage silsesquioxanes, also known as polyhedral oligomeric silsesquioxanes (Polyhedral Oligomeric Silsesquioxanes, POSS), refer to a class of structural formula (RSiO 1.5 )n compounds, whose spatial structure is regular, can be divided into T according to the number of repeating units n 8 , T 10 , T 12 , R refers to hydrogen, alkyl, aryl and the like. POSS compounds are organic / inorganic hybrid substances at the molecular level, which contain an inorganic skeleton composed of Si-O (SiO 1.5 )n, connecting an organic substituent group R at its apex. The three-dimensional size of POSS is about 1-3 nm. [0003] One or more reactive functional substituents are connected to the vertices of the unique cage structure of POSS, and the nanostructured POSS can b...

Claims

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Application Information

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IPC IPC(8): C08G77/52C07F7/02C08L83/14C03C17/30
Inventor 黄发荣杜磊周燕李强邓诗峰
Owner EAST CHINA UNIV OF SCI & TECH
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