Aryne modified resin containing silicon

A technology for modifying resin and silicon aryl alkyne, applied in the field of silicon-containing aryl alkyne modified resin, can solve the problems of unsatisfactory fiber cohesion, high brittleness, poor mechanical properties of composite materials, etc.

Inactive Publication Date: 2008-02-27
EAST CHINA UNIV OF SCI & TECH +1
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AI Technical Summary

Problems solved by technology

Such as: Luneva etc. utilize the reaction of acetylene Grignard reagent and alkyl, aryl silicon halide to prepare silicon-containing alkyne resin (L.K.Luneva, A.M.Sladkov, and V.V.Korshak, Vysokomolekulyamye Soedineniya, Seriya A, 1967, 9 (4) : 910-14.), its heat resistance can reach 450 ° C ~ 550 ° C; Itoh et al. used magnesium oxide as a catalyst to synthesize a silicon hydroaryne resin - MSP resin (a.M.Itoh, M.Mitsuzuka, K.Iwata , K.Inoue.Macromolecules, 1994, 27:7917-7917.b.M.Itoh, K.Inoue, et al., Journal of Materials Science, 2002, 37:3795.), has excellent thermal properties after curing, but due to the material The brittleness and shrinkage in the curing process lead to poor mechanical properties of the composite material; Ohshita et al. successfully synthesized a series of silicon-containing polymers whose side groups are aryne groups by metal lithium method (a.J.Ohshita, A.Yamashita, The class The polymer has excellent thermal stability, and the weight loss rate at 1000 ° C is 17%; Buvat et al. have synthesized a phenylacetylene-terminated silicon-hydroaryne resin (called BLJ resin) (Pierrick Buvat., et al., SAMPE Symp. , 2000, 46: 134-144), the cured resin does not have a glass transition below 450 ° C, and the residual rate of decomposition at 1000 ° C under argon is 80%; Huang Farong et al. have also prepared silicon-containing aryne resins with various structures ( CN 1709928)
[0004] In summary, although the existing silicon-containing aryne resins have their own characteristics, their common problems are: the brittleness of the silicon-containing aryne resin after curing is too high, and the adhesion to the fiber is not ideal

Method used

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  • Aryne modified resin containing silicon
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  • Aryne modified resin containing silicon

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preparation example Construction

[0018] (1) Preparation of arylethynyl benzoxazine compounds:

[0019] The bulk condensation method is used to prepare the arylethynyl benzoxazine compounds described in the present invention. This method has the advantages of simple operation, low cost, and less environmental pollution. details as follows:

[0020] Phenolic compounds, m-aminophenylacetylene and paraformaldehyde are placed in a reaction kettle, stirred, heated to 90°C to 110°C, and maintained under this condition for 20 to 40 minutes. Lower the temperature and dissolve the obtained product in halogenated hydrocarbon (such as chloroform, etc.), wash with 3 mol / L sodium hydroxide aqueous solution, and then wash with deionized water until neutral. Finally, the solvent (halogenated hydrocarbon) is evaporated to obtain the arylethynyl benzoxazine compounds of the present invention.

[0021] Wherein the recommended phenolic compound is hydroquinone, 1,4'-diphenol, 1,5-naphthalenediol or the compound shown in formul...

Embodiment 1

[0042] The synthesis of bisphenol A type arylethynyl benzoxazine [compound shown in formula (4)]:

[0043]Add stoichiometric bisphenol A 11.4g (0.0500mol), paraformaldehyde 6.01g (0.200mol), m-aminophenylacetylene 11.7g (0.100mol) ). Heat to 100°C under stirring, and react for 20 minutes. After the reaction, the product was dissolved in chloroform, washed three times with 3 mol / L sodium hydroxide solution, and then washed with deionized water until neutral. Finally, the solvent is distilled off to obtain arylethynyl benzoxazine resin. The yield was 73.7%. 1 H-NMR (CDCl 3 , TMS) δ: 1.60 (C-CH 3 ), 3.06(C≡CH), 4.56(Ar-CH 2 -N), 5.30 (O-CH 2 -N).

[0044]

[0045] Synthesis of dimethyl type silicon-containing aryne polymer [compound shown in formula (5)]:

[0046] Add treated 6.00g (0.247mol) magnesium powder and 50ml THF into a 250ml four-neck flask equipped with a stirring, constant pressure funnel and spherical condenser, and then slowly add 21.6g (0.198mol) of mag...

Embodiment 2

[0052] Synthesis of hexafluorobisphenol A type arylethynyl benzoxazine [compound shown in formula (6)]:

[0053] Add stoichiometric hexafluorobisphenol A16.8g (0.0500mol), paraformaldehyde 6.01g (0.200mol), m-aminophenylacetylene 11.7g ( 0.100mol). Heat to 100°C under stirring, and react for 20 minutes. After the reaction, the product was dissolved in chloroform, washed three times with 3 mol / L sodium hydroxide solution, and then washed with deionized water until neutral. Finally, the solvent was distilled off to obtain arylethynyl benzoxazine resin with a yield of 75.3%.

[0054] 1 H-NMR (CDCl 3 , TMS) δ: 3.06 (C≡CH), 4.60 (Ar-CH 2 -N), 5.36 (O-CH 2 -N).

[0055]

[0056] Preparation of dimethyl silicon-containing aryne modified resin DM-FBPA30:

[0057] Put 12.0g of the compound represented by the formula (6) and 28.0g of the compound represented by the formula (5) into a reaction kettle equipped with a stirrer, a thermometer and a reflux condenser, slowly raise t...

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Abstract

The invention relates to a modified resin with silicon aryne modified by aryne ethynylbenzene and oxazine compound, which is copolymerized by 50-95wt% aryne ethynylbenzene and 5-50wt% oxazine compound, wherein the silicon aryne polymeric compound has the structure as formula (1). The invention improves the modified resin including silicon aryne to be good thermostable property, which displays good dynamic property and fabric recombination property. R is hydrocarbyl group of fatty group or aromatic and R' is hydrocarbyl group of H or C1-C6 fatty group or aromatic in formula (1), n is 1-15.

Description

technical field [0001] The invention relates to a silicon-containing aryne-modified resin, in particular to a silicon-containing aryne-modified resin modified by an arylethynyl benzoxazine compound. Background technique [0002] Silicon-containing aryne resin is a new type of aryne-based thermosetting resin. In addition to the characteristics of aryne-based resins, it also has excellent electrical properties and high-temperature ceramic properties (that is, in this type of polymer at high temperature Can form stable ceramic structures such as SiC or / and SiO 2 Wait). [0003] So far, silicon-containing aryne resins with various structures have been reported. Such as: Luneva etc. utilize the reaction of acetylene Grignard reagent and alkyl, aryl silicon halide to prepare silicon-containing alkyne resin (L.K.Luneva, A.M.Sladkov, and V.V.Korshak, Vysokomolekulyamye Soedineniya, Seriya A, 1967, 9 (4) : 910-14.), its heat resistance can reach 450 ° C ~ 550 ° C; Itoh et al. used...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F238/00
Inventor 黄发荣杜磊黄健翔张健齐会民尹国光周燕万里强
Owner EAST CHINA UNIV OF SCI & TECH
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