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Aromatic cyanate ester monomer containing silicon and preparation method thereof

A technology for aromatic cyanate ester and cyanate ester, which is applied in the field of cyanate ester monomer and its preparation, and can solve the problems of reducing key physical properties and having no cyanate ester compound with aryl silicon structure.

Inactive Publication Date: 2012-05-23
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with other resin matrices such as polymaleimide, epoxy resin, etc., cyanate resin has better toughness, but many of its other properties, such as fracture resistance, need to be improved. Many additives, including thermoplastic resins, epoxy resins, etc. , bismaleimide, etc. are used for their toughening, but it will always reduce one or more of the key physical properties
However, there are no reports of cyanate ester compounds with aryl silicon structure

Method used

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  • Aromatic cyanate ester monomer containing silicon and preparation method thereof
  • Aromatic cyanate ester monomer containing silicon and preparation method thereof
  • Aromatic cyanate ester monomer containing silicon and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Synthesis of bis(4-bromophenyl)disilane: Dissolve 25g of 1,4-p-dibromobenzene in 80ml of tetrahydrofuran, cool to -78°C, slowly add 31.2ml of 2.5N n-butyllithium n-hexane solution dropwise, After the dropwise addition was completed and the stirring was continued for 0.5 hours, 2.4 ml of diphenyldichlorosilane was added dropwise. After the dropwise addition, the reaction was continued for 5 hours, and the reaction was terminated with dilute hydrochloric acid aqueous solution. The organic phase was separated, dried with anhydrous magnesium sulfate, and the solvent was spin-dried, and the residue was recrystallized with ethyl acetate to obtain 14 g of white crystals with a yield of 87.4%.

[0024] Synthesis of bis(4-hydroxyphenyl)disilane: Dissolve 1.9g of bis(4-bromophenyl)disilane in 40ml of tetrahydrofuran, cool to -78°C, slowly add dropwise 3.7ml of 2.5N n-butyllithium n-hexane solution, after the dropwise addition, add 3.5ml of trimethyl borate dropwise, c...

Embodiment 2

[0029]

[0030] Synthesis of tris(4-bromophenyl)phenylsilane: Dissolve 18g of 1,4-p-dibromobenzene in 80ml of tetrahydrofuran, cool down to -78°C, and slowly add 47.4ml of 2.5N n-butyllithium n-hexane solution dropwise After the dropwise addition was completed and stirring was continued for 4 hours, 1.5 ml of phenyltrichlorosilane was added dropwise, and after the dropwise addition was completed, the reaction was continued for 2 hours, and the reaction was terminated with dilute hydrochloric acid aqueous solution. The organic phase was separated, dried with anhydrous magnesium sulfate, and the solvent was spin-dried, and the residue was recrystallized with dichloromethane to obtain 2 g of white crystals with a yield of 89.2%.

[0031] Synthesis of tris(4-hydroxyphenyl)phenylsilane: Dissolve 2.3g of tetrakis(4-bromophenyl)silane in 50ml of tetrahydrofuran, cool to -78°C, slowly add 9.3ml of 2.5N n-butyl lithium dropwise n-hexane solution, after the dropwise addition, add 2.5...

Embodiment 3

[0036]

[0037] Synthesis of tetrakis(4-bromophenyl)silane: Dissolve 25g of 1,4-p-dibromobenzene in 80ml of tetrahydrofuran, cool to -78°C, slowly add 63.2ml of 2.5N n-butyllithium n-hexane solution dropwise, After the dropwise addition was completed and stirring was continued for 1 hour, 2.5 ml of tetrachlorosilane was added dropwise, and the reaction was continued for 2 hours after the dropwise addition, and the reaction was terminated with dilute hydrochloric acid aqueous solution. The organic phase was separated, dried with anhydrous magnesium sulfate, and the solvent was spin-dried, and the residue was recrystallized with dichloromethane to obtain 16 g of white crystals with a yield of 93.7%.

[0038] Synthesis of tetrakis(4-hydroxyphenyl)silane: Dissolve 1.3g of tetrakis(4-bromophenyl)silane in 50ml of tetrahydrofuran, cool down to -78°C, slowly add 7.3ml of 2.5N n-butyllithium n-hexane solution dropwise After the dropwise addition, 3.5ml of trimethyl borate was added...

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PUM

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Abstract

The invention provides an aromatic cyanate ester monomer containing silicon and a preparation method thereof. The structure of the cyanate ester resin monomer is as follow; in the formula, n is the integer between 2 and 4. The cyanate ester resin monomer is prepared by taking the chlorosilane as the original material, synthesizing an aromatic polyphenol monomer containing silicon, then reacting with the cyan halide. The aromatic cyanate ester monomer containing silicon has high reaction activity. The prepared resin has good thermooxidation resistance and the humidity resistance, is suitable as a substrate for a new high performance polymer composite material and is applied to the fields of the printed circuit board and the aerospace material, wherein the polyfunctional group resin is especially suitable for the low dielectric coefficient material and the polyporous material field owing to the special space network structure.

Description

technical field [0001] The invention relates to a cyanate monomer and a preparation method thereof, in particular to a silicon-containing aromatic cyanate monomer and a preparation method thereof. technical background [0002] Cyanate resin is a new type of resin matrix containing two or more cyanate functional groups (-O-C≡N), which has the characteristics of excellent heat resistance, low toxicity and low moisture absorption of polyimide , and can be cured and molded by a molding process similar to that of epoxy resin, and the monomer or prepolymer does not emit volatile components during curing. This high-performance thermosetting resin has excellent properties such as high glass transition temperature, low dielectric constant and dielectric loss, small thermal expansion coefficient, and high bonding strength to metals. It is widely used in the fields of electronics, aviation, and adhesive industries. Compared with other resin matrices such as polymaleimide, epoxy resin,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/10
Inventor 王忠刚张步峰
Owner DALIAN UNIV OF TECH
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