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Diethynylphenylaminosilane modified silicon-containing aryne resin and preparation method thereof

A technology of diethynylaniline silane and ethynyl aniline silane, which is applied in the field of silicon-containing aryne resin modified by diethynyl aniline silane and its preparation field, can solve the problem of high brittleness of cured products, low thermal performance and mechanical properties of composite materials Low-level problems, to achieve excellent mechanical properties and heat resistance, excellent heat resistance, and low melt viscosity

Active Publication Date: 2015-09-09
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Japan's Itoh etc. synthesized the silicon-containing aryne resin-MSP resin (M Itoh, M Mitsuzuka, et al, Macromolecules, 1994, 27: 7917~7919) containing silicon-hydrogen bond with magnesium oxide as catalyst dehydrogenation, cured product has Excellent thermal performance, but there are disadvantages such as material brittleness and large curing shrinkage, and the mechanical properties of the composite material are low; France's Buvat et al. have prepared a phenylacetylene-terminated silicon-containing aryne resin-BLJ resin (FR2862307), and its molecular weight is easy. control, but the thermal performance is relatively low; the domestic Huang Farong project combined a series of silicon-containing aryne resins (ZL200510027518.5) with different structures, which improved the process performance, storage stability and mechanical properties of silicon-containing aryne resins.
[0004] Although the silicon-containing aryne resin has excellent heat resistance, there are still defects such as high brittleness of the cured product and poor bonding performance with fibers, which greatly limits its wide application in aerospace and other fields.

Method used

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  • Diethynylphenylaminosilane modified silicon-containing aryne resin and preparation method thereof
  • Diethynylphenylaminosilane modified silicon-containing aryne resin and preparation method thereof
  • Diethynylphenylaminosilane modified silicon-containing aryne resin and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Dimethyl-bis(3-ethynylaniline)-silane modified silicon-containing aryne resin (SZa / PSA-20) and its preparation

[0030] 1. Synthesis of dimethyl-bis(3-ethynylaniline)-silane (SZa)

[0031] In a 250ml four-necked flask equipped with a stirrer, a reflux condenser, a thermometer and a vent, nitrogen protection was added, and 30ml of triethylamine (5.05g, 0.050mol) and 3-aminophenylacetylene (5.85g, 0.050mol) were added. Toluene solution, and it was cooled to -10°C, and a mixed solution of 30ml of toluene and dimethyldichlorosilane (3.25g, 0.025mol) was slowly added dropwise to it through a 50ml constant pressure funnel, and reacted for 1h after the dropwise addition was completed. Then heat up to 25°C to react for 4 hours. After the reaction, filter with suction, wash the filtrate with water 4 to 5 times, remove the water with anhydrous sodium sulfate, remove the solvent by rotary evaporation, and recrystallize to obtain white crystals with a melting point of 90.7°C. yl-b...

Embodiment 2

[0040] Dimethyl-bis(3-ethynylaniline)-silane modified silicon-containing aryne resin (SZa / PSA-40) and its preparation

[0041] Add SZa (40g) and PSA (60g) into a flask equipped with a stirrer, a thermometer and a reflux condenser, protect it with nitrogen, slowly heat up to 110°C and start stirring, and continue stirring for 0.5h after the reactants are completely melted. A reddish-brown modified silicon-containing aryne resin was obtained.

[0042] The reddish-brown resin has a viscosity of less than 0.4 Pa s in the range of 100-190°C, and begins to gel when the viscosity rises rapidly at 200°C; DSC test shows that the resin curing initial exothermic temperature is 209°C, and the peak exothermic temperature is 257°C. The exothermic end temperature is 296°C; the resin is cured in sections at 150°C / 2h, 170°C / 2h, and 210°C / 2h, and post-treated at 250°C / 4h to obtain a cured resin. In a nitrogen atmosphere, the thermal decomposition temperature of the cured product, that is, the ...

Embodiment 3

[0044] Diphenyl-bis(3-ethynylaniline)-silane modified silicon-containing aryne resin (SZb / PSA-10) and its preparation

[0045] 1. Synthesis of diphenyl-bis(3-ethynylaniline)-silane (SZb)

[0046] In a 250ml four-necked flask equipped with a stirrer, a reflux condenser, a thermometer and a vent, nitrogen protection was added, and 30ml of triethylamine (5.05g, 0.050mol) and 3-aminophenylacetylene (5.85g, 0.050mol) were added. Toluene solution, and it was cooled to -10°C, and a mixed solution of 30ml toluene and diphenyldichlorosilane (6.40g, 0.025mol) was slowly added dropwise to it through a 50ml constant pressure funnel, and reacted for 1h after the dropwise addition was completed , and then heated up to 70°C for 4 hours. After the reaction, filter with suction, wash the filtrate 4 to 5 times with water, remove the water with anhydrous sodium sulfate, remove the solvent by rotary evaporation, and precipitate a white solid with a melting point of 130.7°C, which is diphenyl yl-...

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Abstract

The present invention relates to a diethynylphenylaminosilane modified silicon-containing aryne resin, wherein 10-40 parts by weight of diethynylphenylaminosilane SZ and 60-90 parts by weight of a silicon-containing aryne resin PSA react for 0.5-4 h at a temperature of 100-150 DEG C under a stirring reaction under the protection of an inert gas to prepare the diethynylphenylaminosilane modified silicon-containing aryne resin. According to the present invention, the diethynylphenylaminosilane modified silicon-containing aryne resin has excellent forming process characteristics such as low melt viscosity, good solubility, low curing temperature, no small molecular gas release during curing, and the like, the cured product has excellent high temperature resistance and provides excellent adhesion with fibers, the quartz fiber-reinforced composite material has excellent mechanical property and dielectric property, and the resin of the present invention can be used in rge high-tech fields of aviation, aerospace and the like.

Description

【Technical field】 [0001] The invention relates to the technical field of resin production, in particular to a silicon-containing aryne resin modified by diethynylaniline silane and a preparation method thereof. 【Background technique】 [0002] Silicon-containing aryne resin is an organic-inorganic hybrid material developed in recent years. It has outstanding heat resistance, excellent dielectric properties and high-temperature ceramic properties. It can be used as high-temperature-resistant materials, wave-transparent materials, and ablation-resistant materials. And high-temperature ceramic precursors, etc., have broad application prospects. [0003] So far, many scholars have done in-depth research on silicon-containing aryne resins. Japan's Itoh etc. synthesized the silicon-containing aryne resin-MSP resin (M Itoh, M Mitsuzuka, et al, Macromolecules, 1994, 27: 7917~7919) containing silicon-hydrogen bond with magnesium oxide as catalyst dehydrogenation, cured product has E...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G77/62
Inventor 黄发荣杜磊周燕杨建辉汪强步晓君李晓杰
Owner EAST CHINA UNIV OF SCI & TECH
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